634:
804:
439:
972:
1329:
1205:
24:
135:
260:
b: InChI=1S/C35H34N4O6.Mg/c1-7-18-15(3)22-11-23-16(4)20(9-10-28(41)42)32(38-23)30-31(35(44)45-6)34(43)29-17(5)24(39-33(29)30)12-26-19(8-2)21(14-40)27(37-26)13-25(18)36-22;/h7,11-14,16,20,31H,1,8-10H2,2-6H3,(H3,36,37,38,39,40,41,42,43);/q;+2/p-2/t16-,20-,31+;/m0./s1
250:
a: InChI=1S/C35H36N4O5.Mg/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22;/h8,12-14,17,21,31H,1,9-11H2,2-7H3,(H3,36,37,38,39,40,41,42);/q;+2/p-2/t17-,21-,31+;/m0./s1
1907:"Origin of the Two Carbonyl Oxygens of Bacteriochlorophyll a. Demonstration of two Different Pathways for the Formation of Ring e in Rhodobacter sphaeroides and Roseobacter denitrificans, and a Common Hydratase Mechanism for 3-acetyl Group Formation"
1311:
are the light harvesting pigments found in photosynthetic bacteria: they do not produce oxygen as a side-product. There are many such structures but all are biosynthetically related by being derived from chlorophyllide
1807:"The Chlorophyll Biosynthetic Enzyme Mg-Protoporphyrin IX Monomethyl Ester (Oxidative) Cyclase (Characterization and Partial Purification from Chlamydomonas reinhardtii and Synechocystis sp. PCC 6803)"
1435:
1946:
Parham, Ramin; Rebeiz, Constantin A. (1992). "Chloroplast biogenesis: [4-vinyl] chlorophyllide a reductase is a divinylchlorophyllide a-specific, NADPH-dependent enzyme".
820:
1505:
1475:
1409:
1258:
1185:
1112:
1069:
1014:
965:
854:
789:
718:
1424:
2022:
Muraki N, Nomata J, Ebata K, Mizoguchi T, Shiba T, Tamiaki H, Kurisu G, Fujita Y (May 2010). "X-ray crystal structure of the light-independent protochlorophyllide reductase".
2515:
1025:
894:
the same overall transformation occurs but the oxygen incorporated into magnesium-protoporphyrin IX 13-monomethyl ester comes from water in the reaction
2413:
2540:
807:
The chlorin ring system forms as the esterified propionate sidechain is cyclised on to the main porphyrin ring to form divinylprotochlorophyllide
2679:
1854:
Stuart, David; Sandström, Malin; Youssef, Helmy M.; Zakhrabekova, Shakhira; Jensen, Poul Erik; Bollivar, David W.; Hansson, Mats (2020-09-08).
1368:) of the pyrrole ring B, giving the characteristic 18-electron aromatic system of many bacteriochlorophylls. This is carried out by the enzyme
751:
2368:
276:
1086:
catalysed by an enzyme which can take a variety of substrates and perform the required vinyl-group reduction, for example in this case
930:
1419:
The next two steps convert the vinyl group first into a 1-hydroxyethyl group and then into the acetyl group of bacteriochlorophyllide
2744:
2075:"Synthesis of chlorophyll b: Localization of chlorophyllide a oxygenase and discovery of a stable radical in the catalytic subunit"
2073:
Eggink, Laura L.; Lobrutto, Russell; Brune, Daniel C.; Brusslan, Judy; Yamasato, Akihiro; Tanaka, Ayumi; Hoober, J Kenneth (2004).
2301:
471:
929:
of the macrocycle is retained. These reactions proceed independently and in some organisms the sequence is reversed. The enzyme
811:
The chlorin ring system features a five-membered carbon ring E is created when one of the propionate groups of the porphyrin is
1758:"Purification and kinetic characterization of the magnesium protoporphyrin IX methyltransferase from Synechocystis PCC6803"
56:)-3-(2-carboxyethyl)-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-9-vinyl-23,25-didehydrophorbine-23,25-diide
2174:
Tsuzuki, Yuki; Tsukatani, Yusuke; Yamakawa, Hisanori; Itoh, Shigeru; Fujita, Yuichi; Yamamoto, Haruki (29 March 2022).
2242:
877:
241:
2126:"Pre-Loading of Chlorophyll Synthase with Tetraprenyl Diphosphate is an Obligatory Step in Chlorophyll Biosynthesis"
577:
into protoporphyrin IX in for example mammals gives haem, the oxygen-carrying cofactor in blood, but plants combine
2786:
1079:
In the organisms which use this alternative sequence of reduction steps, the process is completed by the reaction
344:
990:
512:
1735:
2176:"Effects of Light and Oxygen on Chlorophyll d Biosynthesis in a Marine Cyanobacterium Acaryochloris marina"
1528:
1515:
These three enzyme-catalysed reactions can occur in different sequences to produce bacteriochlorophyllide
2294:
1905:
Porra, Robert J.; Schafer, Wolfram; Gad'On, Nasr; Katheder, Ingrid; Drews, Gerhart; Scheer, Hugo (1996).
1490:
1460:
1394:
1243:
1170:
1097:
1054:
999:
950:
839:
774:
703:
589:
Details of the late stages of the biosynthetic pathway to chlorophyll differ in the plants (for example
1369:
1134:
2225:
Senge, Mathias O.; Smith, Kevin M. (2004). "Biosynthesis and
Structures of the Bacteriochlorophylls".
1856:"Aerobic Barley Mg-protoporphyrin IX Monomethyl Ester Cyclase is Powered by Electrons from Ferredoxin"
2262:
792:
508:
1527:
is not attached directly: rather, the initial intermediate is the ester with R=geranylgeranyl (from
284:
a: CCC1=C(C)C2=Cc3c(C=C)c(C)c4C=C5(C)(CCC(O)=O)C6=55(n34)n3c(=CC1=25)c(C)c1C(=O)(C(=O)OC)C6=c31
1439:
1428:
1373:
1227:
1150:
1080:
1033:
983:
938:
895:
824:
759:
664:
1365:
1360:
890:
2781:
2609:
2287:
1354:
914:
685:
555:
193:
2708:
2687:
2615:
1040:
720:
559:
40:
975:
The reduction of ring D of protochlorophyllide completes the biosynthesis of chlorophyllide
185:
2605:
2595:
2319:
2031:
1655:
1223:
769:
645:
591:
528:
427:
399:
110:
102:
2125:
8:
2601:
2556:
2530:
1308:
934:
885:
660:
524:
516:
91:
2035:
1659:
164:
156:
2721:
2591:
2202:
2175:
2156:
2055:
1999:
1982:
1882:
1855:
1782:
1757:
1681:
1624:
403:
2101:
2074:
1831:
1806:
925:
and the second adds two atoms of hydrogen to the pyrrole ring D, although the overall
2520:
2448:
2398:
2238:
2207:
2148:
2106:
2047:
2004:
1963:
1928:
1923:
1906:
1887:
1836:
1787:
1716:
1699:
Battersby, A. R. (2000). "Tetrapyrroles: the
Pigments of Life. A Millennium review".
1673:
1616:
1578:
633:
603:
597:
570:
227:
1628:
2734:
2643:
2637:
2587:
2380:
2230:
2197:
2187:
2160:
2140:
2096:
2086:
2059:
2039:
1994:
1955:
1918:
1877:
1867:
1826:
1818:
1777:
1769:
1708:
1685:
1663:
1608:
1570:
1296:, both made from corresponding chlorophyllides ultimately made from chlorophyllide
482:
299:
219:
1561:
Willows, Robert D. (2003). "Biosynthesis of chlorophylls from protoporphyrin IX".
1523:
to the final pigments for photosynthesis. The phytyl ester of bacteriochlorophyll
1032:
as its cofactor and is not dependent on light; it performs the a similar reaction
2700:
2458:
2403:
2343:
812:
520:
459:
581:
instead to give, after further transformations, chlorophyll for photosynthesis.
2477:
2453:
1520:
803:
494:
388:
338:
1612:
2775:
2752:
2661:
2655:
2579:
2548:
2408:
2229:. Advances in Photosynthesis and Respiration. Vol. 2. pp. 137–151.
873:
613:
544:
500:
438:
419:
381:
374:
2234:
2673:
2353:
2311:
2211:
2192:
2152:
2110:
2051:
1891:
1840:
1791:
1720:
1620:
1582:
1341:
1328:
971:
504:
467:
370:
2091:
2008:
1981:
Apel, Klaus; Santel, Hans-Joachim; Redlinger, Tom E.; Falk, Heinz (2005).
1967:
1932:
1872:
1677:
1599:
Bollivar, David W. (2007). "Recent advances in chlorophyll biosynthesis".
827:
750:) ester on one of the propionate groups, which is catalysed by the enzyme
746:
The next step towards the chlorophyllides is the formation of a methyl (CH
488:
2651:
2348:
2279:
2124:
Schmid, H. C.; Rassadina, V.; Oster, U.; Schoch, S.; RĂĽdiger, W. (2002).
1822:
1442:
1431:
1337:
926:
922:
918:
898:
755:
584:
567:
450:, the methyl group show in the green box is replaced with a formyl group.
407:
2144:
2043:
1959:
1736:"3,8-divinyl-chlorophyllide a biosynthesis I (aerobic, light-dependent)"
1531:) which is then subject to additional steps as three of the sidechain's
1376:
1230:
1153:
1083:
986:
941:
762:
2669:
2525:
2431:
2390:
2338:
1773:
1226:
completes the biosynthesis of chlorophyll a by catalysing the reaction
1036:
1029:
869:
667:
532:
326:
175:
2468:
2440:
2333:
1712:
1668:
1643:
1574:
1273:
1024:
This reaction is light-dependent but there is an alternative enzyme,
724:
578:
551:
1204:
337:
Except where otherwise noted, data are given for materials in their
2729:
2358:
1983:"The Protochlorophyllide Holochrome of Barley (Hordeum vulgare L.)"
1644:"Biosynthesis of the pigments of life: formation of the macrocycle"
1268:
This forms an ester of the carboxylic acid group in chlorophyllide
909:
Two further transformations are required to produce chlorophyllide
563:
540:
479:
23:
1853:
1303:
819:
rings C and D. A series of chemical steps catalysed by the enzyme
402:
in the final step of the pathway. Thus the main interest in these
134:
2625:
1047:
3,8-divinylprotochlorophyllide + reduced ferredoxin + 2 ATP + 2 H
816:
653:
205:
821:
Magnesium-protoporphyrin IX monomethyl ester (oxidative) cyclase
741:
2507:
2501:
2495:
2489:
1532:
1277:
865:
657:
649:
622:
411:
392:
1904:
1641:
1319:
833:
Mg-protoporphyrin IX 13-monomethyl ester + 3 NADPH + 3 H + 3 O
618:
415:
395:
146:
123:
2173:
1642:
Battersby AR, Fookes CJ, Matcham GW, McDonald E (May 1980).
1122:
2485:
2072:
1352:
is a typical example; its biosynthesis has been studied in
574:
536:
2123:
2021:
1199:
880:: the cyclase protein is named XanL and is encoded by the
499:
In the early steps of the biosynthesis, which starts from
642:
1756:
Shepherd, Mark; Reid, James D.; Hunter, C. Neil (2003).
1026:
Ferredoxin:protochlorophyllide reductase (ATP-dependent)
1980:
489:
Biosynthesis steps up to formation of protoporphyrin IX
478:) and highlighted in the green box, is replaced with a
904:
656:. The metal is inserted into protoporphyrin IX by the
617:) in which it has been studied. However, although the
585:
Biosynthesis of chlorophyllides from protoporphyrin IX
1493:
1463:
1397:
1246:
1173:
1100:
1057:
1002:
989:
in which the pyrrole ring D is reduced by the enzyme
953:
842:
777:
706:
625:
vary, the chemical reactions involved are identical.
1483:
3-deacetyl 3-(1-hydroxyethyl)bacteriochlorophyllide
1477:
3-deacetyl 3-(1-hydroxyethyl)bacteriochlorophyllide
1284:
is made by the same enzyme acting on chlorophyllide
641:Chlorophyll is characterised by having a magnesium
554:and chlorophyll itself. The next intermediates are
1755:
1499:
1469:
1403:
1252:
1179:
1106:
1063:
1008:
959:
848:
783:
712:
2773:
226:
218:
1304:Use in the biosynthesis of bacteriochlorophylls
426:is also an intermediate in the biosynthesis of
109:
101:
1727:
2578:
2295:
2263:"Pathway: bacteriochlorophyll a biosynthesis"
1804:
752:Magnesium protoporphyrin IX methyltransferase
742:Esterification of the ring C propionate group
1945:
798:
637:Magnesium is inserted into protoporphyrin IX
1141:is the enzyme that converts chlorophyllide
1075:+ oxidized ferredoxin + 2 ADP + 2 phosphate
947:3,8-divinylprotochlorophyllide + NADPH + H
933:converts 3,8-divinylprotochlorophyllide to
2309:
2302:
2288:
2256:
2254:
2224:
1594:
1592:
931:divinyl chlorophyllide a 8-vinyl-reductase
192:
184:
2201:
2191:
2100:
2090:
1998:
1922:
1881:
1871:
1830:
1781:
1698:
1667:
1449:3-deacetyl 3-vinylbacteriochlorophyllide
1415:+ 2 oxidized ferredoxin + ADP + phosphate
1411:3-deacetyl 3-vinylbacteriochlorophyllide
856:divinylprotochlorophyllide + 3 NADP + 5 H
628:
2260:
1805:Bollivar DW, Beale SI (September 1996).
1733:
1598:
1556:
1554:
1552:
1550:
1548:
1364:. The first step is the reduction (with
1340:or 1-hydroxyethyl group in place of the
1327:
1203:
970:
815:to the carbon atom linking the original
802:
632:
437:
2251:
2167:
1589:
1560:
1200:Use in the biosynthesis of chlorophylls
791:Mg-protoporphyrin IX 13-methyl ester +
2774:
1436:bacteriochlorophyllide a dehydrogenase
868:the electrons are provided by reduced
2283:
1545:
1324:: bacteriochlorin ring and sidechains
263:Key: QPDWBRHRBKXUNS-IEEIVXFASA-L
253:Key: ANWUQYTXRXCEMZ-NYABAGMLSA-L
163:
155:
2265:. MetaCyc Metabolic Pathway Database
1738:. MetaCyc Metabolic Pathway Database
1336:(R=H). Earlier intermediates have a
1288:. The same is known for chlorophyll
1500:{\displaystyle \rightleftharpoons }
1470:{\displaystyle \rightleftharpoons }
1404:{\displaystyle \rightleftharpoons }
1253:{\displaystyle \rightleftharpoons }
1180:{\displaystyle \rightleftharpoons }
1149:by catalysing the overall reaction
1107:{\displaystyle \rightleftharpoons }
1064:{\displaystyle \rightleftharpoons }
1009:{\displaystyle \rightleftharpoons }
960:{\displaystyle \rightleftharpoons }
905:Reduction steps to chlorophyllide a
849:{\displaystyle \rightleftharpoons }
784:{\displaystyle \rightleftharpoons }
713:{\displaystyle \rightleftharpoons }
208:
13:
2227:Anoxygenic Photosynthetic Bacteria
2000:10.1111/j.1432-1033.1980.tb06100.x
14:
2798:
1423:. The reactions are catalysed by
982:This is followed by the reaction
1987:European Journal of Biochemistry
1924:10.1111/j.1432-1033.1996.0085u.x
1911:European Journal of Biochemistry
1387:+ 2 reduced ferredoxin + ATP + H
996:protochlorophyllide + NADPH + H
22:
2218:
2117:
2066:
2015:
1974:
1939:
1372:, which catalyses the reaction
1043:3,8-divinylprotochlorophyllide
341:(at 25 °C , 100 kPa).
1898:
1847:
1798:
1749:
1692:
1635:
1494:
1464:
1398:
1247:
1174:
1101:
1058:
1003:
954:
843:
778:
707:
1:
1538:
1094:+ 2 reduced ferredoxin + 2 H
991:protochlorophyllide reductase
872:, which can obtain them from
663:which catalyzes the reaction
433:
1529:geranylgeranyl pyrophosphate
1425:chlorophyllide a 3-hydratase
878:Ferredoxin—NADP(+) reductase
607:) and bacteria (for example
82:: Chlorophyllide b
76:: Chlorophyllide a
7:
823:gives the overall reaction
727:+ Mg-protoporphyrin IX + 2
446:, (R=H). In chlorophyllide
331:614.973 g/mol
10:
2803:
1370:chlorophyllide a reductase
1090:3,8-divinylchlorophyllide
1071:3,8-divinylchlorophyllide
967:protochlorophyllide + NADP
917:reactions: one converts a
531:. The latter is the first
507:is created by the enzymes
495:Porphyrin § Synthesis
492:
2743:
2720:
2699:
2624:
2569:
2539:
2476:
2467:
2439:
2430:
2389:
2376:
2367:
2329:
2318:
1613:10.1007/s11120-006-9076-6
1039:but with the alternative
799:From porphyrin to chlorin
793:S-adenosyl-L-homocysteine
462:(R=H). In chlorophyllide
406:has been in the study of
335:
292:
272:
237:
66:
61:
39:
34:
21:
2516:Magnesium protoporphyrin
391:groups are converted to
2787:Photosynthetic pigments
2261:R. Caspi (2015-12-08).
2235:10.1007/0-306-47954-0_8
1734:R. Caspi (2007-07-18).
1701:Natural Product Reports
1601:Photosynthesis Research
1563:Natural Product Reports
1507:bacteriochlorophyllide
1361:Rhodobacter sphaeroides
1332:Bacteriochlorophyllide
1118:+ 2 oxidized ferredoxin
891:Rhodobacter sphaeroides
768:Mg-protoporphyrin IX +
535:intermediate common to
2193:10.3390/plants11070915
1501:
1471:
1405:
1355:Rhodobacter capsulatus
1345:
1254:
1220:
1181:
1108:
1065:
1010:
979:
961:
876:or, in the dark, from
850:
808:
785:
714:
638:
629:Insertion of magnesium
609:Rubrivivax gelatinosus
556:coproporphyrinogen III
451:
2616:Protoporphyrinogen IX
2092:10.1186/1471-2229-4-5
1873:10.3390/plants9091157
1502:
1472:
1406:
1366:trans stereochemistry
1331:
1255:
1240:+ phytyl diphosphate
1207:
1182:
1109:
1066:
1011:
974:
962:
851:
806:
786:
715:
636:
560:protoporphyrinogen IX
441:
2709:Bacteriochlorophyll
2688:Bacteriochlorophyll
2133:Biological Chemistry
1823:10.1104/pp.112.1.105
1491:
1461:
1395:
1348:Bacteriochlorophyll
1309:Bacteriochlorophylls
1244:
1224:Chlorophyll synthase
1171:
1123:From chlorophyllide
1098:
1055:
1028:, that uses reduced
1000:
951:
840:
775:
770:S-adenosylmethionine
704:
673:protoporphyrin IX +
592:Arabidopsis thaliana
529:uroporphyrinogen III
428:bacteriochlorophylls
400:chlorophyll synthase
387:respectively. Their
2722:Isobacteriochlorins
2557:Protochlorophyllide
2531:Zinc protoporphyrin
2145:10.1515/BC.2002.198
2044:10.1038/nature08950
2036:2010Natur.465..110M
1960:10.1021/bi00151a011
1762:Biochemical Journal
1660:1980Natur.285...17B
1535:bonds are reduced.
1272:with the 20-carbon
935:protochlorophyllide
886:anaerobic organisms
661:magnesium chelatase
525:hydroxymethylbilane
517:aminolevulinic acid
474:for chlorophyllide
18:
2602:Coproporphyrinogen
1774:10.1042/BJ20021394
1497:
1467:
1401:
1346:
1250:
1221:
1177:
1145:to chlorophyllide
1127:to chlorophyllide
1104:
1061:
1006:
980:
957:
846:
809:
781:
710:
639:
452:
404:chemical compounds
345:Infobox references
81:
75:
16:
2769:
2768:
2765:
2764:
2761:
2760:
2565:
2564:
2521:Protoporphyrin IX
2449:Adenosylcobalamin
2426:
2425:
2422:
2421:
2399:Phycoerythrobilin
2079:BMC Plant Biology
1954:(36): 8460–8464.
604:Triticum aestivum
598:Nicotiana tabacum
571:protoporphyrin IX
422:. Chlorophyllide
353:Chemical compound
351:
350:
136:Interactive image
79:
73:
2794:
2735:Sirohydrochlorin
2701:Bacteriochlorins
2588:Uroporphyrinogen
2576:
2575:
2474:
2473:
2437:
2436:
2381:Phytochromobilin
2374:
2373:
2327:
2326:
2304:
2297:
2290:
2281:
2280:
2274:
2273:
2271:
2270:
2258:
2249:
2248:
2222:
2216:
2215:
2205:
2195:
2171:
2165:
2164:
2130:
2121:
2115:
2114:
2104:
2094:
2070:
2064:
2063:
2019:
2013:
2012:
2002:
1978:
1972:
1971:
1943:
1937:
1936:
1926:
1902:
1896:
1895:
1885:
1875:
1851:
1845:
1844:
1834:
1811:Plant Physiology
1802:
1796:
1795:
1785:
1753:
1747:
1746:
1744:
1743:
1731:
1725:
1724:
1713:10.1039/B002635M
1696:
1690:
1689:
1671:
1669:10.1038/285017a0
1639:
1633:
1632:
1596:
1587:
1586:
1575:10.1039/B110549N
1558:
1506:
1504:
1503:
1498:
1476:
1474:
1473:
1468:
1410:
1408:
1407:
1402:
1259:
1257:
1256:
1251:
1186:
1184:
1183:
1178:
1167:+ 2 NADPH + 2 H
1113:
1111:
1110:
1105:
1070:
1068:
1067:
1062:
1015:
1013:
1012:
1007:
966:
964:
963:
958:
855:
853:
852:
847:
790:
788:
787:
782:
737:
736:
735:
719:
717:
716:
711:
700:
698:
697:
683:
682:
681:
515:which transform
470:at position 13 (
410:biosynthesis in
300:Chemical formula
230:
222:
210:
196:
188:
167:
159:
138:
113:
105:
29:Chlorophyllide a
26:
19:
15:
2802:
2801:
2797:
2796:
2795:
2793:
2792:
2791:
2772:
2771:
2770:
2757:
2739:
2716:
2695:
2620:
2571:
2561:
2541:Phytoporphyrins
2535:
2478:Protoporphyrins
2463:
2459:Methylcobalamin
2418:
2414:Phycoviolobilin
2404:Phycocyanobilin
2385:
2363:
2344:Stercobilinogen
2322:
2314:
2308:
2278:
2277:
2268:
2266:
2259:
2252:
2245:
2223:
2219:
2172:
2168:
2139:(11): 1769–78.
2128:
2122:
2118:
2071:
2067:
2030:(7294): 110–4.
2020:
2016:
1979:
1975:
1944:
1940:
1903:
1899:
1852:
1848:
1803:
1799:
1754:
1750:
1741:
1739:
1732:
1728:
1697:
1693:
1654:(5759): 17–21.
1640:
1636:
1597:
1590:
1559:
1546:
1541:
1492:
1489:
1488:
1462:
1459:
1458:
1456:
1396:
1393:
1392:
1390:
1383:chlorophyllide
1326:
1306:
1245:
1242:
1241:
1236:chlorophyllide
1202:
1194:
1187:chlorophyllide
1172:
1169:
1168:
1166:
1159:chlorophyllide
1135:Chlorophyllide
1132:
1114:chlorophyllide
1099:
1096:
1095:
1056:
1053:
1052:
1050:
1016:chlorophyllide
1001:
998:
997:
952:
949:
948:
907:
859:
841:
838:
837:
836:
801:
776:
773:
772:
749:
744:
734:
732:
731:
730:
728:
705:
702:
701:
696:
693:
692:
691:
689:
680:
678:
677:
676:
674:
631:
587:
573:. Insertion of
548:
521:porphobilinogen
497:
491:
472:IUPAC numbering
460:carboxylic acid
454:Chlorophyllide
442:Chlorophyllide
436:
364:Chlorophyllide
357:Chlorophyllide
354:
347:
342:
320:
316:
312:
308:
302:
288:
285:
280:
279:
268:
265:
264:
261:
255:
254:
251:
245:
244:
233:
211:
199:
170:
141:
127:
116:
94:
85:
57:
30:
27:
17:Chlorophyllide
12:
11:
5:
2800:
2790:
2789:
2784:
2767:
2766:
2763:
2762:
2759:
2758:
2756:
2755:
2749:
2747:
2741:
2740:
2738:
2737:
2732:
2726:
2724:
2718:
2717:
2715:
2714:
2705:
2703:
2697:
2696:
2694:
2693:
2685:
2667:
2649:
2634:Chlorophyllide
2630:
2628:
2622:
2621:
2619:
2618:
2613:
2599:
2584:
2582:
2580:Porphyrinogens
2573:
2567:
2566:
2563:
2562:
2560:
2559:
2554:
2545:
2543:
2537:
2536:
2534:
2533:
2528:
2523:
2518:
2513:
2482:
2480:
2471:
2465:
2464:
2462:
2461:
2456:
2454:Cyanocobalamin
2451:
2445:
2443:
2434:
2428:
2427:
2424:
2423:
2420:
2419:
2417:
2416:
2411:
2406:
2401:
2395:
2393:
2387:
2386:
2384:
2383:
2377:
2371:
2365:
2364:
2362:
2361:
2356:
2351:
2346:
2341:
2336:
2330:
2324:
2316:
2315:
2307:
2306:
2299:
2292:
2284:
2276:
2275:
2250:
2243:
2217:
2166:
2116:
2065:
2014:
1993:(1): 251–258.
1973:
1938:
1897:
1846:
1817:(1): 105–114.
1797:
1768:(2): 351–360.
1748:
1726:
1707:(6): 507–526.
1691:
1634:
1607:(2): 173–194.
1588:
1569:(6): 327–341.
1543:
1542:
1540:
1537:
1521:esterification
1513:
1512:
1496:
1481:
1466:
1454:
1445:) as follows:
1417:
1416:
1400:
1388:
1325:
1318:
1305:
1302:
1280:. Chlorophyll
1266:
1265:
1249:
1201:
1198:
1197:
1196:
1192:
1176:
1164:
1131:
1121:
1120:
1119:
1103:
1077:
1076:
1060:
1048:
1022:
1021:
1005:
969:
968:
956:
906:
903:
862:
861:
857:
845:
834:
800:
797:
796:
795:
780:
747:
743:
740:
739:
738:
733:
709:
694:
679:
630:
627:
586:
583:
546:
493:Main article:
490:
487:
435:
432:
398:by the enzyme
389:propionic acid
373:precursors of
352:
349:
348:
343:
339:standard state
336:
333:
332:
329:
323:
322:
318:
314:
310:
306:
303:
298:
295:
294:
290:
289:
287:
286:
283:
275:
274:
273:
270:
269:
267:
266:
262:
259:
258:
256:
252:
249:
248:
240:
239:
238:
235:
234:
232:
231:
223:
214:
212:
204:
201:
200:
198:
197:
189:
180:
178:
172:
171:
169:
168:
160:
151:
149:
143:
142:
140:
139:
130:
128:
121:
118:
117:
115:
114:
106:
97:
95:
90:
87:
86:
84:
83:
77:
71:
67:
64:
63:
59:
58:
43:
37:
36:
32:
31:
28:
9:
6:
4:
3:
2:
2799:
2788:
2785:
2783:
2782:Tetrapyrroles
2780:
2779:
2777:
2754:
2753:Cofactor F430
2751:
2750:
2748:
2746:
2742:
2736:
2733:
2731:
2728:
2727:
2725:
2723:
2719:
2713:
2712:
2707:
2706:
2704:
2702:
2698:
2692:
2691:
2686:
2683:
2682:
2677:
2676:
2671:
2668:
2665:
2664:
2659:
2658:
2653:
2650:
2647:
2646:
2641:
2640:
2635:
2632:
2631:
2629:
2627:
2623:
2617:
2614:
2611:
2607:
2603:
2600:
2597:
2593:
2589:
2586:
2585:
2583:
2581:
2577:
2574:
2568:
2558:
2555:
2553:
2552:
2547:
2546:
2544:
2542:
2538:
2532:
2529:
2527:
2524:
2522:
2519:
2517:
2514:
2511:
2510:
2505:
2504:
2499:
2498:
2493:
2492:
2487:
2484:
2483:
2481:
2479:
2475:
2472:
2470:
2466:
2460:
2457:
2455:
2452:
2450:
2447:
2446:
2444:
2442:
2438:
2435:
2433:
2429:
2415:
2412:
2410:
2409:Phycourobilin
2407:
2405:
2402:
2400:
2397:
2396:
2394:
2392:
2388:
2382:
2379:
2378:
2375:
2372:
2370:
2366:
2360:
2357:
2355:
2352:
2350:
2347:
2345:
2342:
2340:
2337:
2335:
2332:
2331:
2328:
2325:
2321:
2317:
2313:
2312:tetrapyrroles
2305:
2300:
2298:
2293:
2291:
2286:
2285:
2282:
2264:
2257:
2255:
2246:
2244:0-7923-3681-X
2240:
2236:
2232:
2228:
2221:
2213:
2209:
2204:
2199:
2194:
2189:
2185:
2181:
2177:
2170:
2162:
2158:
2154:
2150:
2146:
2142:
2138:
2134:
2127:
2120:
2112:
2108:
2103:
2098:
2093:
2088:
2084:
2080:
2076:
2069:
2061:
2057:
2053:
2049:
2045:
2041:
2037:
2033:
2029:
2025:
2018:
2010:
2006:
2001:
1996:
1992:
1988:
1984:
1977:
1969:
1965:
1961:
1957:
1953:
1949:
1942:
1934:
1930:
1925:
1920:
1916:
1912:
1908:
1901:
1893:
1889:
1884:
1879:
1874:
1869:
1865:
1861:
1857:
1850:
1842:
1838:
1833:
1828:
1824:
1820:
1816:
1812:
1808:
1801:
1793:
1789:
1784:
1779:
1775:
1771:
1767:
1763:
1759:
1752:
1737:
1730:
1722:
1718:
1714:
1710:
1706:
1702:
1695:
1687:
1683:
1679:
1675:
1670:
1665:
1661:
1657:
1653:
1649:
1645:
1638:
1630:
1626:
1622:
1618:
1614:
1610:
1606:
1602:
1595:
1593:
1584:
1580:
1576:
1572:
1568:
1564:
1557:
1555:
1553:
1551:
1549:
1544:
1536:
1534:
1530:
1526:
1522:
1518:
1510:
1486:
1482:
1480:
1452:
1448:
1447:
1446:
1444:
1441:
1437:
1433:
1430:
1426:
1422:
1414:
1386:
1382:
1381:
1380:
1378:
1375:
1371:
1367:
1363:
1362:
1357:
1356:
1351:
1343:
1339:
1335:
1330:
1323:
1317:
1315:
1310:
1301:
1299:
1295:
1291:
1287:
1283:
1279:
1275:
1271:
1264:+ diphosphate
1263:
1239:
1235:
1234:
1233:
1232:
1229:
1225:
1219:
1215:
1211:
1206:
1190:
1162:
1158:
1157:
1156:
1155:
1152:
1148:
1144:
1140:
1138:
1130:
1126:
1117:
1093:
1089:
1088:
1087:
1085:
1082:
1074:
1046:
1045:
1044:
1042:
1038:
1035:
1031:
1027:
1019:
995:
994:
993:
992:
988:
985:
978:
973:
946:
945:
944:
943:
940:
936:
932:
928:
924:
920:
916:
912:
902:
900:
897:
893:
892:
887:
883:
879:
875:
874:photosystem I
871:
867:
832:
831:
830:
829:
826:
822:
818:
814:
805:
794:
771:
767:
766:
765:
764:
761:
757:
753:
726:
722:
687:
672:
671:
670:
669:
666:
662:
659:
655:
651:
647:
644:
635:
626:
624:
620:
616:
615:
614:Synechocystis
610:
606:
605:
600:
599:
594:
593:
582:
580:
576:
572:
569:
566:to the fully
565:
561:
557:
553:
549:
542:
538:
534:
530:
526:
522:
518:
514:
510:
506:
502:
501:glutamic acid
496:
486:
484:
481:
477:
473:
469:
465:
461:
457:
449:
445:
440:
431:
429:
425:
421:
420:cyanobacteria
417:
413:
409:
405:
401:
397:
394:
390:
386:
385:
379:
378:
372:
368:
367:
361:
360:
346:
340:
334:
330:
328:
325:
324:
304:
301:
297:
296:
291:
282:
281:
278:
271:
257:
247:
246:
243:
236:
229:
224:
221:
216:
215:
213:
207:
203:
202:
195:
190:
187:
182:
181:
179:
177:
174:
173:
166:
161:
158:
153:
152:
150:
148:
145:
144:
137:
132:
131:
129:
125:
120:
119:
112:
107:
104:
99:
98:
96:
93:
89:
88:
78:
72:
69:
68:
65:
60:
55:
51:
47:
42:
38:
33:
25:
20:
2710:
2689:
2680:
2674:
2662:
2656:
2644:
2638:
2633:
2550:
2549:Chlorophyll
2508:
2502:
2496:
2490:
2354:Urobilinogen
2267:. Retrieved
2226:
2220:
2183:
2179:
2169:
2136:
2132:
2119:
2082:
2078:
2068:
2027:
2023:
2017:
1990:
1986:
1976:
1951:
1948:Biochemistry
1947:
1941:
1917:(1): 85–92.
1914:
1910:
1900:
1863:
1859:
1849:
1814:
1810:
1800:
1765:
1761:
1751:
1740:. Retrieved
1729:
1704:
1700:
1694:
1651:
1647:
1637:
1604:
1600:
1566:
1562:
1524:
1516:
1514:
1508:
1484:
1478:
1450:
1420:
1418:
1412:
1384:
1359:
1353:
1349:
1347:
1342:acetyl group
1333:
1321:
1313:
1307:
1297:
1293:
1289:
1285:
1281:
1269:
1267:
1261:
1260:chlorophyll
1237:
1222:
1217:
1213:
1209:
1208:Chlorophyll
1188:
1160:
1146:
1142:
1136:
1133:
1128:
1124:
1115:
1091:
1078:
1072:
1023:
1017:
981:
976:
937:in reaction
910:
908:
889:
881:
863:
810:
745:
640:
612:
608:
602:
596:
590:
588:
513:cosynthetase
505:tetrapyrrole
498:
475:
468:methyl group
463:
455:
453:
447:
443:
423:
383:
382:chlorophyll
376:
375:chlorophyll
371:biosynthetic
365:
363:
358:
356:
355:
62:Identifiers
53:
49:
45:
44:Magnesium (3
2652:Chlorophyll
2391:Phycobilins
2369:Phytobilins
2349:Stercobilin
1866:(9): 1157.
1338:vinyl group
927:aromaticity
923:ethyl group
919:vinyl group
913:. Both are
756:methylation
646:coordinated
562:, which is
533:macrocyclic
408:chlorophyll
293:Properties
165:CHEBI:38209
157:CHEBI:16900
2776:Categories
2670:Pheophytin
2572:porphyrins
2526:Pterobilin
2469:Porphyrins
2441:Corrinoids
2432:Macrocycle
2339:Biliverdin
2269:2020-06-04
2186:(7): 915.
1742:2020-06-04
1539:References
1519:ready for
1511:+ NADH + H
1195:O + 2 NADP
1030:ferredoxin
870:ferredoxin
828:1.14.13.81
545:cofactor F
434:Structures
327:Molar mass
176:ChemSpider
122:3D model (
111:14428-12-7
103:14897-06-4
92:CAS Number
41:IUPAC name
2334:Bilirubin
2310:Types of
1495:⇌
1465:⇌
1443:1.1.1.396
1432:4.2.1.165
1399:⇌
1274:diterpene
1248:⇌
1175:⇌
1139:oxygenase
1102:⇌
1059:⇌
1041:substrate
1004:⇌
955:⇌
915:reduction
899:1.21.98.3
884:gene. In
844:⇌
779:⇌
763:2.1.1.11
758:reaction
725:phosphate
708:⇌
652:called a
648:within a
579:magnesium
552:cobalamin
509:deaminase
70:Compounds
2745:Corphins
2730:Siroheme
2626:Chlorins
2359:Urobilin
2323:(Linear)
2212:35406896
2153:12530542
2111:15086960
2052:20400946
1892:32911631
1841:12226378
1792:12489983
1721:11152419
1629:23808539
1621:17370354
1583:12828371
1391:O + 2 H
1377:1.3.7.15
1276:alcohol
1231:2.5.1.62
1154:1.3.7.13
1084:1.3.7.13
987:1.3.1.33
942:1.3.1.75
888:such as
882:Xantha-l
813:cyclised
568:aromatic
564:oxidised
541:sirohaem
369:are the
228:15775275
225:b:
217:a:
194:34999243
191:b:
183:a:
162:b:
154:a:
133:a:
108:b:
100:a:
2570:Reduced
2320:Bilanes
2203:9003380
2161:3099209
2060:4427639
2032:Bibcode
2009:7439188
1968:1390630
1933:8706723
1883:7570240
1783:1223276
1686:9070849
1678:6769048
1656:Bibcode
1037:1.3.7.7
817:pyrrole
754:in the
668:6.6.1.1
654:chlorin
623:enzymes
458:, is a
321:
206:PubChem
2241:
2210:
2200:
2180:Plants
2159:
2151:
2109:
2102:406501
2099:
2058:
2050:
2024:Nature
2007:
1966:
1931:
1890:
1880:
1860:Plants
1839:
1832:157929
1829:
1790:
1780:
1719:
1684:
1676:
1648:Nature
1627:
1619:
1581:
1533:alkene
1487:+ NAD
1434:) and
1344:shown.
1278:phytol
1216:, and
1020:+ NADP
921:to an
866:barley
658:enzyme
650:ligand
480:formyl
466:, the
412:plants
396:esters
393:phytyl
277:SMILES
220:439664
186:388735
35:Names
2157:S2CID
2129:(PDF)
2085:: 5.
2056:S2CID
1682:S2CID
1625:S2CID
1320:BChl
1191:+ 3 H
1163:+ 2 O
619:genes
483:group
416:algae
242:InChI
147:ChEBI
124:JSmol
2486:Heme
2239:ISBN
2208:PMID
2149:PMID
2107:PMID
2048:PMID
2005:PMID
1964:PMID
1929:PMID
1888:PMID
1837:PMID
1788:PMID
1717:PMID
1674:PMID
1617:PMID
1579:PMID
1358:and
1292:and
621:and
611:and
601:and
575:iron
558:and
537:haem
523:and
519:via
511:and
503:, a
418:and
380:and
362:and
2610:III
2596:III
2231:doi
2198:PMC
2188:doi
2141:doi
2137:383
2097:PMC
2087:doi
2040:doi
2028:465
1995:doi
1991:111
1956:doi
1919:doi
1915:239
1878:PMC
1868:doi
1827:PMC
1819:doi
1815:112
1778:PMC
1770:doi
1766:371
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