81:. This procedure can then be repeated again to identify the next amino acid. A major drawback to this technique is that the peptides being sequenced in this manner cannot have more than 50 to 60 residues (and in practice, under 30). The peptide length is limited due to the cyclical derivatization not always going to completion. The derivatization problem can be resolved by cleaving large peptides into smaller peptides before proceeding with the reaction. It is able to accurately
54:
72:
conditions, this derivative of the terminal amino acid is cleaved as a thiazolinone derivative. The thiazolinone amino acid is then selectively extracted into an organic solvent and treated with acid to form the more stable phenylthiohydantoin (PTH)- amino acid derivative that can be identified by
133:
Following 2D SDS PAGE the proteins can be transferred to a polyvinylidene difluoride (PVDF) blotting membrane for further analysis. Edman degradations can be performed directly from a PVDF membrane. N-terminal residue sequencing resulting in five to ten amino acid may be sufficient to identify a
125:), since the favored five-membered ring intermediate is unable to be formed. Edman degradation is generally not useful to determine the positions of disulfide bridges. It also requires peptide amounts of 1 picomole or above for discernible results.
1240:
101:
for the sequencing process. The Edman degradation reaction was automated in 1967 by Edman and Beggs to speed up the process and 100 automated devices were in use worldwide by 1973.
3455:
2571:
2516:
3284:
2626:
2776:
1410:
3505:
3279:
1105:
2381:
302:
2951:
2151:
895:
3116:
3046:
3026:
2521:
1688:
1150:
1569:
1125:
338:
2871:
3349:
3299:
1703:
2806:
3445:
3254:
2911:
2891:
2851:
1658:
601:
260:
3440:
3370:
3269:
2926:
2781:
2411:
2256:
1866:
1493:
1270:
3520:
3304:
2616:
2106:
1781:
2326:
3515:
3229:
3091:
2881:
2846:
3405:
3344:
2876:
2791:
2761:
2741:
2606:
2601:
1976:
1901:
1544:
1498:
1365:
626:
3510:
3470:
3420:
3096:
2896:
2646:
2576:
1065:
636:
2711:
1604:
1325:
3264:
3106:
2976:
2971:
2786:
2261:
2171:
1761:
1693:
1584:
1160:
915:
840:
295:
3021:
3629:
3550:
3435:
3334:
3274:
2921:
2716:
2676:
2651:
2561:
2021:
1055:
985:
621:
551:
2141:
3540:
3126:
3016:
2636:
2361:
2146:
2091:
1936:
1896:
1728:
1483:
1200:
1050:
3500:
3061:
2506:
3535:
3450:
3425:
3400:
3385:
3309:
3224:
3121:
3081:
2946:
2901:
2666:
2211:
2196:
2061:
1851:
1519:
1275:
955:
930:
900:
491:
64:
is reacted with an uncharged N-terminal amino group, under mildly alkaline conditions, to form a cyclical
3485:
3430:
3375:
3086:
3006:
2906:
2621:
2586:
2431:
2321:
2036:
2031:
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1330:
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2401:
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456:
288:
2751:
1015:
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3056:
2986:
2941:
2916:
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2011:
2001:
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1450:
1310:
1305:
1285:
970:
767:
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631:
451:
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3101:
3011:
2981:
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2641:
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2186:
1743:
1683:
1648:
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1435:
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2991:
3624:
3619:
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1971:
1718:
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1205:
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2501:
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2056:
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1265:
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571:
348:
343:
3570:
3156:
3111:
2826:
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2701:
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1916:
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1811:
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1733:
1599:
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1554:
1375:
1335:
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1190:
945:
815:
790:
328:
143:
8:
3614:
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3131:
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2816:
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2226:
2216:
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1946:
1821:
1796:
1708:
1564:
1549:
1534:
1355:
1300:
1070:
920:
865:
736:
651:
511:
436:
113:
of the protein, it will not work if the N-terminus has been chemically modified (e.g. by
38:
3555:
2206:
1390:
581:
3294:
3244:
3214:
3076:
2866:
2656:
2541:
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2231:
2161:
2126:
2121:
2101:
2096:
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1951:
1801:
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1220:
1140:
1035:
935:
870:
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506:
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220:
203:
27:
252:
3031:
2351:
2236:
2201:
2166:
2111:
2066:
1981:
1961:
1911:
1906:
1876:
1861:
1678:
1614:
1579:
1405:
1280:
1155:
1080:
1060:
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566:
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363:
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118:
2026:
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2311:
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2241:
2016:
1826:
1806:
1776:
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1609:
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1425:
1380:
1370:
1360:
1255:
1235:
1230:
1215:
1210:
1090:
1085:
1025:
1010:
1000:
845:
835:
701:
691:
591:
586:
561:
501:
353:
312:
248:
215:
181:
681:
3475:
3166:
3001:
2996:
2291:
2276:
2221:
2176:
2136:
2086:
2051:
2046:
1991:
1986:
1921:
1871:
1791:
1619:
1503:
1478:
1440:
1415:
1400:
1385:
1320:
1195:
1145:
1135:
1115:
1075:
885:
875:
860:
656:
576:
446:
416:
401:
396:
148:
78:
3480:
3390:
3329:
2421:
2331:
2301:
2076:
1931:
1668:
1445:
1315:
1130:
1100:
800:
696:
471:
333:
74:
280:
3593:
3490:
3191:
3036:
2931:
2726:
2116:
2081:
2071:
2006:
1996:
1886:
1723:
1539:
1250:
1225:
1095:
741:
726:
711:
606:
536:
516:
431:
42:
2531:
1891:
1643:
1420:
1020:
820:
671:
666:
531:
386:
122:
270:
229:
1030:
676:
646:
411:
168:
Edman, P.; Högfeldt, Erik; Sillén, Lars Gunnar; Kinell, Per-Olof (1950).
114:
86:
30:
243:
Niall HD (1973). "Automated edman degradation: The protein sequenator".
3314:
2841:
2191:
110:
90:
23:
93:. An advantage of the Edman degradation is that it only uses 10 - 100
721:
391:
121:). Sequencing will stop if a non-α-amino acid is encountered (e.g.
82:
53:
381:
170:"Method for determination of the amino acid sequence in peptides"
98:
34:
69:
41:
is labeled and cleaved from the peptide without disrupting the
94:
247:. Methods in Enzymology. Vol. 27. pp. 942–1010.
167:
89:
with modern machines capable of over 99% efficiency per
57:
Edman degradation with generic amino acid peptide chain
3456:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
2517:Divinylcyclopropane-cycloheptadiene rearrangement
3591:
109:Because the Edman degradation proceeds from the
310:
201:
2777:Thermal rearrangement of aromatic hydrocarbons
1411:Thermal rearrangement of aromatic hydrocarbons
3506:Lectka enantioselective beta-lactam synthesis
766:
296:
16:Method of sequencing amino acids in a peptide
3285:Inverse electron-demand Diels–Alder reaction
1106:Heterogeneous metal catalyzed cross-coupling
2627:Lobry de Bruyn–Van Ekenstein transformation
303:
289:
3117:Petrenko-Kritschenko piperidone synthesis
2572:Fritsch–Buttenberg–Wiechell rearrangement
219:
185:
3280:Intramolecular Diels–Alder cycloaddition
242:
52:
3592:
3300:Metal-centered cycloaddition reactions
2952:Debus–Radziszewski imidazole synthesis
896:Bodroux–Chichibabin aldehyde synthesis
37:. In this method, the amino-terminal
3446:Diazoalkane 1,3-dipolar cycloaddition
3350:Vinylcyclopropane (5+2) cycloaddition
3255:Diazoalkane 1,3-dipolar cycloaddition
3027:Hurd–Mori 1,2,3-thiadiazole synthesis
2522:Dowd–Beckwith ring-expansion reaction
1689:Hurd–Mori 1,2,3-thiadiazole synthesis
765:
602:LFER solvent coefficients (data page)
284:
2257:Sharpless asymmetric dihydroxylation
1494:Methoxymethylenetriphenylphosphorane
2382:Allen–Millar–Trippett rearrangement
128:
45:between other amino acid residues.
13:
3521:Nitrone-olefin (3+2) cycloaddition
3516:Niementowski quinazoline synthesis
3305:Nitrone-olefin (3+2) cycloaddition
3230:Azide-alkyne Huisgen cycloaddition
3092:Niementowski quinazoline synthesis
2847:Azide-alkyne Huisgen cycloaddition
2152:Meerwein–Ponndorf–Verley reduction
1704:Leimgruber–Batcho indole synthesis
221:10.1111/j.1432-1033.1967.tb00047.x
14:
3641:
3345:Trimethylenemethane cycloaddition
3047:Johnson–Corey–Chaykovsky reaction
2912:Cadogan–Sundberg indole synthesis
2892:Bohlmann–Rahtz pyridine synthesis
2852:Baeyer–Emmerling indole synthesis
1659:Cadogan–Sundberg indole synthesis
1151:Johnson–Corey–Chaykovsky reaction
3441:Cook–Heilbron thiazole synthesis
3270:Hexadehydro Diels–Alder reaction
3097:Niementowski quinoline synthesis
2927:Cook–Heilbron thiazole synthesis
2872:Bischler–Möhlau indole synthesis
2782:Tiffeneau–Demjanov rearrangement
2412:Baker–Venkataraman rearrangement
1570:Horner–Wadsworth–Emmons reaction
1241:Mizoroki-Heck vs. Reductive Heck
1126:Horner–Wadsworth–Emmons reaction
637:Neighbouring group participation
2977:Fiesselmann thiophene synthesis
2807:Westphalen–Lettré rearrangement
2787:Vinylcyclopropane rearrangement
2617:Kornblum–DeLaMare rearrangement
2262:Epoxidation of allylic alcohols
2172:Noyori asymmetric hydrogenation
2107:Kornblum–DeLaMare rearrangement
1782:Gallagher–Hollander degradation
187:10.3891/acta.chem.scand.04-0283
3436:Chichibabin pyridine synthesis
2922:Chichibabin pyridine synthesis
2882:Blum–Ittah aziridine synthesis
2717:Ring expansion and contraction
986:Cross dehydrogenative coupling
236:
202:Edman P, Begg G (March 1967).
195:
161:
104:
1:
3406:Bischler–Napieralski reaction
3364:Heterocycle forming reactions
3017:Hemetsberger indole synthesis
2877:Bischler–Napieralski reaction
2792:Wagner–Meerwein rearrangement
2762:Sommelet–Hauser rearrangement
2742:Seyferth–Gilbert homologation
2607:Ireland–Claisen rearrangement
2602:Hofmann–Martius rearrangement
2362:2,3-sigmatropic rearrangement
1977:Corey–Winter olefin synthesis
1902:Barton–McCombie deoxygenation
1545:Corey–Winter olefin synthesis
1499:Seyferth–Gilbert homologation
1366:Seyferth–Gilbert homologation
253:10.1016/S0076-6879(73)27039-8
154:
3511:Lehmstedt–Tanasescu reaction
3471:Gabriel–Colman rearrangement
3426:Bucherer carbazole synthesis
3421:Borsche–Drechsel cyclization
3401:Bernthsen acridine synthesis
3386:Bamberger triazine synthesis
3371:Algar–Flynn–Oyamada reaction
3082:Nazarov cyclization reaction
2947:De Kimpe aziridine synthesis
2902:Bucherer carbazole synthesis
2897:Borsche–Drechsel cyclization
2667:Nazarov cyclization reaction
2647:Meyer–Schuster rearrangement
2577:Gabriel–Colman rearrangement
2327:Wolffenstein–Böters reaction
2212:Reduction of nitro compounds
2062:Grundmann aldehyde synthesis
1867:Algar–Flynn–Oyamada reaction
1276:Olefin conversion technology
1271:Nozaki–Hiyama–Kishi reaction
1066:Gabriel–Colman rearrangement
956:Claisen-Schmidt condensation
901:Bouveault aldehyde synthesis
48:
7:
3486:Hantzsch pyridine synthesis
3265:Enone–alkene cycloadditions
3087:Nenitzescu indole synthesis
3007:Hantzsch pyridine synthesis
2972:Ferrario–Ackermann reaction
2622:Kowalski ester homologation
2587:Halogen dance rearrangement
2432:Benzilic acid rearrangement
1857:Akabori amino-acid reaction
1817:Von Braun amide degradation
1762:Barbier–Wieland degradation
1714:Nenitzescu indole synthesis
1694:Kharasch–Sosnovsky reaction
1585:Julia–Kocienski olefination
1489:Kowalski ester homologation
1186:Kowalski ester homologation
1161:Julia–Kocienski olefination
916:Cadiot–Chodkiewicz coupling
841:Aza-Baylis–Hillman reaction
786:Acetoacetic ester synthesis
497:Dynamic binding (chemistry)
487:Conrotatory and disrotatory
462:Charge remote fragmentation
137:
134:Protein of Interest (POI).
10:
3646:
3551:Robinson–Gabriel synthesis
3501:Kröhnke pyridine synthesis
3335:Retro-Diels–Alder reaction
3275:Imine Diels–Alder reaction
3062:Kröhnke pyridine synthesis
2677:Newman–Kwart rearrangement
2652:Mislow–Evans rearrangement
2562:Fischer–Hepp rearrangement
2507:Di-Ď€-methane rearrangement
2287:Stephen aldehyde synthesis
2022:Eschweiler–Clarke reaction
1739:Williamson ether synthesis
1056:Fujiwara–Moritani reaction
961:Combes quinoline synthesis
926:Carbonyl olefin metathesis
627:More O'Ferrall–Jencks plot
552:Grunwald–Winstein equation
522:Electron-withdrawing group
457:Catalytic resonance theory
3561:Urech hydantoin synthesis
3541:Pomeranz–Fritsch reaction
3466:Fischer oxazole synthesis
3363:
3200:1,3-Dipolar cycloaddition
3190:
3172:Urech hydantoin synthesis
3142:Reissert indole synthesis
3127:Pomeranz–Fritsch reaction
3057:Knorr quinoline synthesis
2987:Fischer oxazole synthesis
2917:Camps quinoline synthesis
2837:1,3-Dipolar cycloaddition
2825:
2737:Semipinacol rearrangement
2712:Ramberg–Bäcklund reaction
2697:Piancatelli rearrangement
2637:McFadyen–Stevens reaction
2392:Alpha-ketol rearrangement
2340:
2147:McFadyen–Stevens reaction
2092:Kiliani–Fischer synthesis
2012:Elbs persulfate oxidation
1937:Bouveault–Blanc reduction
1897:Baeyer–Villiger oxidation
1835:
1752:
1729:Schotten–Baumann reaction
1632:
1605:Ramberg–Bäcklund reaction
1512:
1484:Kiliani–Fischer synthesis
1464:
1326:Ramberg–Bäcklund reaction
1311:Pinacol coupling reaction
1306:Piancatelli rearrangement
1201:Liebeskind–Srogl coupling
1051:Fujimoto–Belleau reaction
774:
768:List of organic reactions
632:Negative hyperconjugation
377:
319:
3536:Pictet–Spengler reaction
3451:Einhorn–Brunner reaction
3416:Boger pyridine synthesis
3310:Oxo-Diels–Alder reaction
3225:Aza-Diels–Alder reaction
3122:Pictet–Spengler reaction
3022:Hofmann–Löffler reaction
3012:Hegedus indole synthesis
2982:Fischer indole synthesis
2857:Bartoli indole synthesis
2812:Willgerodt rearrangement
2642:McLafferty rearrangement
2552:Ferrier carbocyclization
2367:2,3-Wittig rearrangement
2357:1,2-Wittig rearrangement
2197:Parikh–Doering oxidation
2187:Oxygen rebound mechanism
1852:Adkins–Peterson reaction
1744:Yamaguchi esterification
1684:Hegedus indole synthesis
1649:Bartoli indole synthesis
1520:Bamford–Stevens reaction
1436:Weinreb ketone synthesis
1396:Stork enamine alkylation
1171:Knoevenagel condensation
1041:Ferrier carbocyclization
931:Castro–Stephens coupling
557:Hammett acidity function
547:Free-energy relationship
492:Curtin–Hammett principle
477:Conformational isomerism
245:Part D: Enzyme Structure
68:derivative. Then, under
3496:Knorr pyrrole synthesis
3431:Bucherer–Bergs reaction
3376:Allan–Robinson reaction
3355:Wagner-Jauregg reaction
3147:Ring-closing metathesis
3072:Larock indole synthesis
3052:Knorr pyrrole synthesis
2907:Bucherer–Bergs reaction
2772:Stieglitz rearrangement
2752:Skattebøl rearrangement
2722:Ring-closing metathesis
2582:Group transfer reaction
2547:Favorskii rearrangement
2487:Cornforth rearrangement
2417:Bamberger rearrangement
2322:Wolff–Kishner reduction
2142:Markó–Lam deoxygenation
2037:Fleming–Tamao oxidation
2032:Fischer–Tropsch process
1719:Oxymercuration reaction
1699:Knorr pyrrole synthesis
1525:Barton–Kellogg reaction
1431:Wagner-Jauregg reaction
1351:Ring-closing metathesis
1341:Reimer–Tiemann reaction
1331:Rauhut–Currier reaction
1246:Nef isocyanide reaction
1206:Malonic ester synthesis
1176:Knorr pyrrole synthesis
1111:High dilution principle
1046:Friedel–Crafts reaction
981:Cross-coupling reaction
906:Bucherer–Bergs reaction
891:Blanc chloromethylation
881:Blaise ketone synthesis
856:Baylis–Hillman reaction
851:Barton–Kellogg reaction
826:Allan–Robinson reaction
732:Woodward–Hoffmann rules
467:Charge-transfer complex
3461:Feist–Benary synthesis
3235:Bradsher cycloaddition
3205:4+4 Photocycloaddition
3162:Simmons–Smith reaction
3107:Paternò–Büchi reaction
2967:Feist–Benary synthesis
2957:Dieckmann condensation
2707:Pummerer rearrangement
2687:Oxy-Cope rearrangement
2662:Myers allene synthesis
2612:Jacobsen rearrangement
2527:Electrocyclic reaction
2502:Demjanov rearrangement
2457:Buchner ring expansion
2427:Beckmann rearrangement
2407:Aza-Cope rearrangement
2402:Arndt–Eistert reaction
2377:Alkyne zipper reaction
2297:Transfer hydrogenation
2272:Sharpless oxyamination
2247:Selenoxide elimination
2132:Lombardo methylenation
2057:Griesbaum coozonolysis
1967:Corey–Itsuno reduction
1942:Boyland–Sims oxidation
1882:Angeli–Rimini reaction
1530:Boord olefin synthesis
1474:Arndt–Eistert reaction
1466:Homologation reactions
1266:Nitro-Mannich reaction
1181:Kolbe–Schmitt reaction
991:Cross-coupling partner
911:Buchner ring expansion
831:Arndt–Eistert reaction
597:Kinetic isotope effect
344:Rearrangement reaction
204:"A protein sequenator"
58:
3630:Degradation reactions
3320:Pauson–Khand reaction
3157:Sharpless epoxidation
3112:Pechmann condensation
2992:Friedländer synthesis
2942:Davis–Beirut reaction
2797:Wallach rearrangement
2767:Stevens rearrangement
2702:Pinacol rearrangement
2682:Overman rearrangement
2597:Hofmann rearrangement
2592:Hayashi rearrangement
2557:Ferrier rearrangement
2512:Dimroth rearrangement
2497:Curtius rearrangement
2492:Criegee rearrangement
2472:Claisen rearrangement
2462:Carroll rearrangement
2397:Amadori rearrangement
2387:Allylic rearrangement
2267:Sharpless epoxidation
2002:Dess–Martin oxidation
1927:Bohn–Schmidt reaction
1787:Hofmann rearrangement
1590:Kauffmann olefination
1513:Olefination reactions
1451:Wurtz–Fittig reaction
1286:Palladium–NHC complex
1166:Kauffmann olefination
1121:Homologation reaction
971:Corey–House synthesis
951:Claisen rearrangement
747:Yukawa–Tsuno equation
707:Swain–Lupton equation
687:Spherical aromaticity
622:Möbius–Hückel concept
407:Aromatic ring current
369:Substitution reaction
62:Phenyl isothiocyanate
56:
3526:Paal–Knorr synthesis
3396:Barton–Zard reaction
3340:Staudinger synthesis
3290:Ketene cycloaddition
3260:Diels–Alder reaction
3240:Cheletropic reaction
3220:Alkyne trimerisation
3102:Paal–Knorr synthesis
3067:Kulinkovich reaction
3042:Jacobsen epoxidation
2962:Diels–Alder reaction
2757:Smiles rearrangement
2747:Sigmatropic reaction
2632:Lossen rearrangement
2482:Corey–Fuchs reaction
2447:Boekelheide reaction
2442:Bergmann degradation
2372:Achmatowicz reaction
2157:Methionine sulfoxide
1957:Clemmensen reduction
1917:Bergmann degradation
1847:Acyloin condensation
1812:Strecker degradation
1767:Bergmann degradation
1734:Ullmann condensation
1600:Peterson olefination
1575:Hydrazone iodination
1555:Elimination reaction
1456:Zincke–Suhl reaction
1376:Sonogashira coupling
1336:Reformatsky reaction
1296:Peterson olefination
1261:Nierenstein reaction
1191:Kulinkovich reaction
1006:Diels–Alder reaction
966:Corey–Fuchs reaction
946:Claisen condensation
816:Alkyne trimerisation
791:Acyloin condensation
757:ÎŁ-bishomoaromaticity
717:Thorpe–Ingold effect
329:Elimination reaction
144:Bergmann degradation
3546:Prilezhaev reaction
3531:Pellizzari reaction
3210:(4+3) cycloaddition
3177:Van Leusen reaction
3152:Robinson annulation
3137:Pschorr cyclization
3132:Prilezhaev reaction
2862:Bergman cyclization
2817:Wolff rearrangement
2802:Weerman degradation
2692:Pericyclic reaction
2672:Neber rearrangement
2567:Fries rearrangement
2452:Brook rearrangement
2437:Bergman cyclization
2282:Staudinger reaction
2227:Rosenmund reduction
2217:Reductive amination
2182:Oppenauer oxidation
1972:Corey–Kim oxidation
1947:Cannizzaro reaction
1822:Weerman degradation
1797:Isosaccharinic acid
1709:Mukaiyama hydration
1565:Hofmann elimination
1550:Dehydrohalogenation
1535:Chugaev elimination
1356:Robinson annulation
1301:Pfitzinger reaction
1071:Gattermann reaction
1016:Wulff–Dötz reaction
996:Dakin–West reaction
921:Carbonyl allylation
866:Bergman cyclization
652:Kennedy J. P. Orton
572:Hammond's postulate
542:Flippin–Lodge angle
512:Electromeric effect
437:Beta-silicon effect
422:Baker–Nathan effect
66:phenylthiocarbamoyl
3295:McCormack reaction
3245:Conia-ene reaction
3077:Madelung synthesis
2867:Biginelli reaction
2657:Mumm rearrangement
2542:Favorskii reaction
2477:Cope rearrangement
2467:Chan rearrangement
2232:Rubottom oxidation
2162:Miyaura borylation
2127:Lipid peroxidation
2122:Lindgren oxidation
2102:Kornblum oxidation
2097:Kolbe electrolysis
2042:Fukuyama reduction
1952:Carbonyl reduction
1802:Marker degradation
1664:Diazonium compound
1654:Boudouard reaction
1633:Carbon-heteroatom
1560:Grieco elimination
1346:Rieche formylation
1291:Passerini reaction
1221:Meerwein arylation
1141:Hydroxymethylation
1036:Favorskii reaction
936:Chan rearrangement
871:Biginelli reaction
796:Aldol condensation
642:2-Norbornyl cation
617:Möbius aromaticity
612:Markovnikov's rule
507:Effective molarity
452:Bürgi–Dunitz angle
442:Bicycloaromaticity
59:
3610:Protein structure
3605:Organic reactions
3600:Molecular biology
3587:
3586:
3583:
3582:
3579:
3578:
3571:Wohl–Aue reaction
3215:6+4 Cycloaddition
3032:Iodolactonization
2352:1,2-rearrangement
2317:Wohl–Aue reaction
2237:Sabatier reaction
2202:Pinnick oxidation
2167:Mozingo reduction
2112:Leuckart reaction
2067:Haloform reaction
1982:Criegee oxidation
1962:Collins oxidation
1912:Benkeser reaction
1907:Bechamp reduction
1877:Andrussow process
1862:Alcohol oxidation
1772:Edman degradation
1679:Haloform reaction
1628:
1627:
1615:Takai olefination
1580:Julia olefination
1406:Takai olefination
1281:Olefin metathesis
1156:Julia olefination
1081:Grignard reaction
1061:Fukuyama coupling
976:Coupling reaction
941:Chan–Lam coupling
811:Alkyne metathesis
806:Alkane metathesis
662:Phosphaethynolate
567:George S. Hammond
527:Electronic effect
482:Conjugated system
364:Stereospecificity
359:Stereoselectivity
324:Addition reaction
313:organic reactions
262:978-0-12-181890-6
119:pyroglutamic acid
26:, is a method of
20:Edman degradation
3637:
3566:Wenker synthesis
3556:Stollé synthesis
3411:Bobbitt reaction
3381:Auwers synthesis
3325:Povarov reaction
3250:Cyclopropanation
3188:
3187:
3182:Wenker synthesis
2937:Darzens reaction
2887:Bobbitt reaction
2732:Schmidt reaction
2537:Enyne metathesis
2312:Whiting reaction
2307:Wharton reaction
2252:Shapiro reaction
2242:Sarett oxidation
2207:Prévost reaction
2017:Emde degradation
1827:Wohl degradation
1807:Ruff degradation
1777:Emde degradation
1674:Grignard reagent
1610:Shapiro reaction
1595:McMurry reaction
1462:
1461:
1426:Ullmann reaction
1391:Stollé synthesis
1381:Stetter reaction
1371:Shapiro reaction
1361:Sakurai reaction
1256:Negishi coupling
1236:Minisci reaction
1231:Michael reaction
1216:McMurry reaction
1211:Mannich reaction
1091:Hammick reaction
1086:Grignard reagent
1026:Enyne metathesis
1011:Doebner reaction
1001:Darzens reaction
846:Barbier reaction
836:Auwers synthesis
763:
762:
737:Woodward's rules
702:Superaromaticity
692:Spiroaromaticity
592:Inductive effect
587:Hyperconjugation
562:Hammett equation
502:Edwards equation
354:Regioselectivity
305:
298:
291:
282:
281:
275:
274:
240:
234:
233:
223:
199:
193:
191:
189:
174:Acta Chem. Scand
165:
129:Coupled analysis
123:isoaspartic acid
117:or formation of
3645:
3644:
3640:
3639:
3638:
3636:
3635:
3634:
3590:
3589:
3588:
3575:
3476:Gewald reaction
3359:
3186:
3167:Skraup reaction
3002:Graham reaction
2997:Gewald reaction
2828:
2821:
2343:
2336:
2292:Swern oxidation
2277:Stahl oxidation
2222:Riley oxidation
2177:Omega oxidation
2137:Luche reduction
2087:Jones oxidation
2052:Glycol cleavage
2047:Ganem oxidation
1992:Davis oxidation
1987:Dakin oxidation
1922:Birch reduction
1872:Amide reduction
1838:
1831:
1792:Hooker reaction
1754:
1748:
1636:
1634:
1624:
1620:Wittig reaction
1508:
1504:Wittig reaction
1479:Hooker reaction
1460:
1441:Wittig reaction
1416:Thorpe reaction
1401:Suzuki reaction
1386:Stille reaction
1321:Quelet reaction
1196:Kumada coupling
1146:Ivanov reaction
1136:Hydrovinylation
1116:Hiyama coupling
1076:Glaser coupling
886:Blaise reaction
876:Bingel reaction
861:Benary reaction
778:
776:
770:
761:
657:Passive binding
577:Homoaromaticity
427:Baldwin's rules
402:Antiaromaticity
397:Anomeric effect
373:
315:
309:
279:
278:
263:
241:
237:
208:Eur. J. Biochem
200:
196:
166:
162:
157:
149:Dansyl chloride
140:
131:
107:
79:electrophoresis
51:
22:, developed by
17:
12:
11:
5:
3643:
3633:
3632:
3627:
3625:Chemical tests
3622:
3620:Name reactions
3617:
3612:
3607:
3602:
3585:
3584:
3581:
3580:
3577:
3576:
3574:
3573:
3568:
3563:
3558:
3553:
3548:
3543:
3538:
3533:
3528:
3523:
3518:
3513:
3508:
3503:
3498:
3493:
3488:
3483:
3481:Hantzsch ester
3478:
3473:
3468:
3463:
3458:
3453:
3448:
3443:
3438:
3433:
3428:
3423:
3418:
3413:
3408:
3403:
3398:
3393:
3391:Banert cascade
3388:
3383:
3378:
3373:
3367:
3365:
3361:
3360:
3358:
3357:
3352:
3347:
3342:
3337:
3332:
3330:Prato reaction
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3292:
3287:
3282:
3277:
3272:
3267:
3262:
3257:
3252:
3247:
3242:
3237:
3232:
3227:
3222:
3217:
3212:
3207:
3202:
3196:
3194:
3185:
3184:
3179:
3174:
3169:
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3114:
3109:
3104:
3099:
3094:
3089:
3084:
3079:
3074:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3034:
3029:
3024:
3019:
3014:
3009:
3004:
2999:
2994:
2989:
2984:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2919:
2914:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2839:
2833:
2831:
2823:
2822:
2820:
2819:
2814:
2809:
2804:
2799:
2794:
2789:
2784:
2779:
2774:
2769:
2764:
2759:
2754:
2749:
2744:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2689:
2684:
2679:
2674:
2669:
2664:
2659:
2654:
2649:
2644:
2639:
2634:
2629:
2624:
2619:
2614:
2609:
2604:
2599:
2594:
2589:
2584:
2579:
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2422:Banert cascade
2419:
2414:
2409:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2369:
2364:
2359:
2354:
2348:
2346:
2342:Rearrangement
2338:
2337:
2335:
2334:
2332:Zinin reaction
2329:
2324:
2319:
2314:
2309:
2304:
2302:Wacker process
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2229:
2224:
2219:
2214:
2209:
2204:
2199:
2194:
2189:
2184:
2179:
2174:
2169:
2164:
2159:
2154:
2149:
2144:
2139:
2134:
2129:
2124:
2119:
2114:
2109:
2104:
2099:
2094:
2089:
2084:
2079:
2077:Hydrogenolysis
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2029:
2027:Étard reaction
2024:
2019:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1974:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1932:Bosch reaction
1929:
1924:
1919:
1914:
1909:
1904:
1899:
1894:
1889:
1884:
1879:
1874:
1869:
1864:
1859:
1854:
1849:
1843:
1841:
1837:Organic redox
1833:
1832:
1830:
1829:
1824:
1819:
1814:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1769:
1764:
1758:
1756:
1750:
1749:
1747:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1696:
1691:
1686:
1681:
1676:
1671:
1669:Esterification
1666:
1661:
1656:
1651:
1646:
1640:
1638:
1630:
1629:
1626:
1625:
1623:
1622:
1617:
1612:
1607:
1602:
1597:
1592:
1587:
1582:
1577:
1572:
1567:
1562:
1557:
1552:
1547:
1542:
1537:
1532:
1527:
1522:
1516:
1514:
1510:
1509:
1507:
1506:
1501:
1496:
1491:
1486:
1481:
1476:
1470:
1468:
1459:
1458:
1453:
1448:
1446:Wurtz reaction
1443:
1438:
1433:
1428:
1423:
1418:
1413:
1408:
1403:
1398:
1393:
1388:
1383:
1378:
1373:
1368:
1363:
1358:
1353:
1348:
1343:
1338:
1333:
1328:
1323:
1318:
1316:Prins reaction
1313:
1308:
1303:
1298:
1293:
1288:
1283:
1278:
1273:
1268:
1263:
1258:
1253:
1248:
1243:
1238:
1233:
1228:
1223:
1218:
1213:
1208:
1203:
1198:
1193:
1188:
1183:
1178:
1173:
1168:
1163:
1158:
1153:
1148:
1143:
1138:
1133:
1131:Hydrocyanation
1128:
1123:
1118:
1113:
1108:
1103:
1101:Henry reaction
1098:
1093:
1088:
1083:
1078:
1073:
1068:
1063:
1058:
1053:
1048:
1043:
1038:
1033:
1028:
1023:
1018:
1013:
1008:
1003:
998:
993:
988:
983:
978:
973:
968:
963:
958:
953:
948:
943:
938:
933:
928:
923:
918:
913:
908:
903:
898:
893:
888:
883:
878:
873:
868:
863:
858:
853:
848:
843:
838:
833:
828:
823:
818:
813:
808:
803:
801:Aldol reaction
798:
793:
788:
782:
780:
775:Carbon-carbon
772:
771:
760:
759:
754:
752:Zaitsev's rule
749:
744:
739:
734:
729:
724:
719:
714:
709:
704:
699:
697:Steric effects
694:
689:
684:
679:
674:
669:
664:
659:
654:
649:
644:
639:
634:
629:
624:
619:
614:
609:
604:
599:
594:
589:
584:
579:
574:
569:
564:
559:
554:
549:
544:
539:
534:
529:
524:
519:
514:
509:
504:
499:
494:
489:
484:
479:
474:
469:
464:
459:
454:
449:
444:
439:
434:
429:
424:
419:
414:
409:
404:
399:
394:
389:
384:
378:
375:
374:
372:
371:
366:
361:
356:
351:
349:Redox reaction
346:
341:
336:
334:Polymerization
331:
326:
320:
317:
316:
308:
307:
300:
293:
285:
277:
276:
261:
235:
194:
159:
158:
156:
153:
152:
151:
146:
139:
136:
130:
127:
106:
103:
75:chromatography
50:
47:
15:
9:
6:
4:
3:
2:
3642:
3631:
3628:
3626:
3623:
3621:
3618:
3616:
3613:
3611:
3608:
3606:
3603:
3601:
3598:
3597:
3595:
3572:
3569:
3567:
3564:
3562:
3559:
3557:
3554:
3552:
3549:
3547:
3544:
3542:
3539:
3537:
3534:
3532:
3529:
3527:
3524:
3522:
3519:
3517:
3514:
3512:
3509:
3507:
3504:
3502:
3499:
3497:
3494:
3492:
3491:Herz reaction
3489:
3487:
3484:
3482:
3479:
3477:
3474:
3472:
3469:
3467:
3464:
3462:
3459:
3457:
3454:
3452:
3449:
3447:
3444:
3442:
3439:
3437:
3434:
3432:
3429:
3427:
3424:
3422:
3419:
3417:
3414:
3412:
3409:
3407:
3404:
3402:
3399:
3397:
3394:
3392:
3389:
3387:
3384:
3382:
3379:
3377:
3374:
3372:
3369:
3368:
3366:
3362:
3356:
3353:
3351:
3348:
3346:
3343:
3341:
3338:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3291:
3288:
3286:
3283:
3281:
3278:
3276:
3273:
3271:
3268:
3266:
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3197:
3195:
3193:
3192:Cycloaddition
3189:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3037:Isay reaction
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2975:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2932:Cycloaddition
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2834:
2832:
2830:
2827:Ring forming
2824:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2727:Rupe reaction
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2373:
2370:
2368:
2365:
2363:
2360:
2358:
2355:
2353:
2350:
2349:
2347:
2345:
2339:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2117:Ley oxidation
2115:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2082:Hydroxylation
2080:
2078:
2075:
2073:
2072:Hydrogenation
2070:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2033:
2030:
2028:
2025:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2007:DNA oxidation
2005:
2003:
2000:
1998:
1997:Deoxygenation
1995:
1993:
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1925:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1887:Aromatization
1885:
1883:
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1848:
1845:
1844:
1842:
1840:
1834:
1828:
1825:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1768:
1765:
1763:
1760:
1759:
1757:
1751:
1745:
1742:
1740:
1737:
1735:
1732:
1730:
1727:
1725:
1724:Reed reaction
1722:
1720:
1717:
1715:
1712:
1710:
1707:
1705:
1702:
1700:
1697:
1695:
1692:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1641:
1639:
1635:bond forming
1631:
1621:
1618:
1616:
1613:
1611:
1608:
1606:
1603:
1601:
1598:
1596:
1593:
1591:
1588:
1586:
1583:
1581:
1578:
1576:
1573:
1571:
1568:
1566:
1563:
1561:
1558:
1556:
1553:
1551:
1548:
1546:
1543:
1541:
1540:Cope reaction
1538:
1536:
1533:
1531:
1528:
1526:
1523:
1521:
1518:
1517:
1515:
1511:
1505:
1502:
1500:
1497:
1495:
1492:
1490:
1487:
1485:
1482:
1480:
1477:
1475:
1472:
1471:
1469:
1467:
1463:
1457:
1454:
1452:
1449:
1447:
1444:
1442:
1439:
1437:
1434:
1432:
1429:
1427:
1424:
1422:
1419:
1417:
1414:
1412:
1409:
1407:
1404:
1402:
1399:
1397:
1394:
1392:
1389:
1387:
1384:
1382:
1379:
1377:
1374:
1372:
1369:
1367:
1364:
1362:
1359:
1357:
1354:
1352:
1349:
1347:
1344:
1342:
1339:
1337:
1334:
1332:
1329:
1327:
1324:
1322:
1319:
1317:
1314:
1312:
1309:
1307:
1304:
1302:
1299:
1297:
1294:
1292:
1289:
1287:
1284:
1282:
1279:
1277:
1274:
1272:
1269:
1267:
1264:
1262:
1259:
1257:
1254:
1252:
1251:Nef synthesis
1249:
1247:
1244:
1242:
1239:
1237:
1234:
1232:
1229:
1227:
1226:Methylenation
1224:
1222:
1219:
1217:
1214:
1212:
1209:
1207:
1204:
1202:
1199:
1197:
1194:
1192:
1189:
1187:
1184:
1182:
1179:
1177:
1174:
1172:
1169:
1167:
1164:
1162:
1159:
1157:
1154:
1152:
1149:
1147:
1144:
1142:
1139:
1137:
1134:
1132:
1129:
1127:
1124:
1122:
1119:
1117:
1114:
1112:
1109:
1107:
1104:
1102:
1099:
1097:
1096:Heck reaction
1094:
1092:
1089:
1087:
1084:
1082:
1079:
1077:
1074:
1072:
1069:
1067:
1064:
1062:
1059:
1057:
1054:
1052:
1049:
1047:
1044:
1042:
1039:
1037:
1034:
1032:
1029:
1027:
1024:
1022:
1019:
1017:
1014:
1012:
1009:
1007:
1004:
1002:
999:
997:
994:
992:
989:
987:
984:
982:
979:
977:
974:
972:
969:
967:
964:
962:
959:
957:
954:
952:
949:
947:
944:
942:
939:
937:
934:
932:
929:
927:
924:
922:
919:
917:
914:
912:
909:
907:
904:
902:
899:
897:
894:
892:
889:
887:
884:
882:
879:
877:
874:
872:
869:
867:
864:
862:
859:
857:
854:
852:
849:
847:
844:
842:
839:
837:
834:
832:
829:
827:
824:
822:
819:
817:
814:
812:
809:
807:
804:
802:
799:
797:
794:
792:
789:
787:
784:
783:
781:
777:bond forming
773:
769:
764:
758:
755:
753:
750:
748:
745:
743:
742:Y-aromaticity
740:
738:
735:
733:
730:
728:
727:Walsh diagram
725:
723:
720:
718:
715:
713:
712:Taft equation
710:
708:
705:
703:
700:
698:
695:
693:
690:
688:
685:
683:
682:ÎŁ-aromaticity
680:
678:
675:
673:
670:
668:
665:
663:
660:
658:
655:
653:
650:
648:
645:
643:
640:
638:
635:
633:
630:
628:
625:
623:
620:
618:
615:
613:
610:
608:
607:Marcus theory
605:
603:
600:
598:
595:
593:
590:
588:
585:
583:
582:HĂĽckel's rule
580:
578:
575:
573:
570:
568:
565:
563:
560:
558:
555:
553:
550:
548:
545:
543:
540:
538:
537:Evelyn effect
535:
533:
530:
528:
525:
523:
520:
518:
517:Electron-rich
515:
513:
510:
508:
505:
503:
500:
498:
495:
493:
490:
488:
485:
483:
480:
478:
475:
473:
470:
468:
465:
463:
460:
458:
455:
453:
450:
448:
445:
443:
440:
438:
435:
433:
432:Bema Hapothle
430:
428:
425:
423:
420:
418:
415:
413:
410:
408:
405:
403:
400:
398:
395:
393:
390:
388:
385:
383:
380:
379:
376:
370:
367:
365:
362:
360:
357:
355:
352:
350:
347:
345:
342:
340:
337:
335:
332:
330:
327:
325:
322:
321:
318:
314:
306:
301:
299:
294:
292:
287:
286:
283:
272:
268:
264:
258:
254:
250:
246:
239:
231:
227:
222:
217:
213:
209:
205:
198:
188:
183:
179:
175:
171:
164:
160:
150:
147:
145:
142:
141:
135:
126:
124:
120:
116:
112:
102:
100:
96:
92:
88:
84:
80:
76:
71:
67:
63:
55:
46:
44:
43:peptide bonds
40:
36:
32:
29:
25:
21:
2532:Ene reaction
1892:Autoxidation
1771:
1753:Degradation
1644:Azo coupling
1421:Ugi reaction
1021:Ene reaction
821:Alkynylation
672:Polyfluorene
667:Polar effect
532:Electrophile
447:Bredt's rule
417:Baird's rule
387:Alpha effect
244:
238:
214:(1): 80–91.
211:
207:
197:
177:
173:
163:
132:
108:
65:
60:
19:
18:
1031:Ethenolysis
677:Ring strain
647:Nucleophile
472:Clar's rule
412:Aromaticity
180:: 283–293.
115:acetylation
105:Limitations
87:amino acids
31:amino acids
3615:Proteomics
3594:Categories
3315:Ozonolysis
2842:Annulation
2192:Ozonolysis
311:Topics in
155:References
111:N-terminus
95:pico-moles
91:amino acid
28:sequencing
24:Pehr Edman
2829:reactions
2344:reactions
1839:reactions
1755:reactions
1637:reactions
779:reactions
85:up to 30
49:Mechanism
722:Vinylogy
392:Annulene
339:Reagents
138:See also
83:sequence
382:A value
271:4773306
230:6059350
99:peptide
39:residue
35:peptide
269:
259:
228:
73:using
70:acidic
33:in a
267:PMID
257:ISBN
226:PMID
249:doi
216:doi
182:doi
97:of
77:or
3596::
265:.
255:.
224:.
210:.
206:.
176:.
172:.
304:e
297:t
290:v
273:.
251::
232:.
218::
212:1
192:.
190:.
184::
178:4
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