84:
50:
704:
20:
152:
in SPPS is very widespread for Fmoc/tBu approach, because its removal with piperidine solution does not disturb the acid-labile linker between the peptide and the resin. A typical SPPS Fmoc deprotection is performed with a solution of 20%
139:
The Fmoc group is rapidly removed by base. Piperidine is usually preferred for Fmoc group removal as it forms a stable adduct with the dibenzofulvene byproduct, preventing it from reacting with the substrate.
91:
372:
Yamada, Kazuhiko; Hashizume, Daisuke; Shimizu, Tadashi; Ohki, Shinobu; Yokoyama, Shigeyuki (2008). "A solid-state 17O NMR, X-ray, and quantum chemical study of N-Ξ±-Fmoc-protected amino acids".
105:
401:"Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates"
354:
in DMF. This method avoids the use of strictly controlled piperidine. No side product was observed for a peptide with 9 residues synthesized with this method.
124:
123:
Because the fluorenyl group is highly fluorescent, certain UV-inactive compounds may be reacted to give the Fmoc derivatives, suitable for analysis by
83:
127:. Analytical uses of Fmoc-Cl that do not use chromatography may be limited by the requirement that excess Fmoc-Cl be removed before an analysis of
482:
75:
347:
581:
528:
599:"Piperazine and DBU: a safer alternative for rapid and efficient Fmoc deprotection in solid phase peptide synthesis"
724:
405:
94:(Fmoc-OSu), which may itself be obtained by the reaction of Fmoc-Cl with the dicyclohexylammonium salt of
729:
434:
Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group".
708:
339:
20% piperidine in DMF (Fmoc group has an approximate half life of 6 seconds in this solution)
158:
646:"Incorporation of Fmoc-Dab(Mtt)-OH during solid-phase peptide synthesis: a word of caution"
610:
95:
8:
614:
469:, Methods in Molecular Biology, vol. 35, Totowa, NJ: Humana Press, pp. 17β27,
681:
113:
520:
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673:
665:
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577:
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488:
478:
43:
657:
618:
569:
551:
J. Jones, Amino Acid and
Peptide Synthesis, 2nd edn., Oxford University Press, 2002
516:
511:
Wellings, Donald A.; Atherton, Eric (1997). "[4] Standard Fmoc protocols".
470:
443:
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381:
67:
39:
35:
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718:
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128:
109:
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Ralhan, Krittika; KrishnaKumar, V. Guru; Gupta, Sharad (8 December 2015).
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492:
351:
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622:
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343:
154:
149:
461:
Fields, Gregg B. (1995), Pennington, Michael W.; Dunn, Ben M. (eds.),
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598:
63:
419:
400:
74:, where the Fmoc group can be introduced by reacting the amine with
90:
The other common method for introducing the Fmoc group is through
148:
The use of Fmoc as a temporary protecting group for amine at the
117:
49:
703:
71:
371:
515:. Methods in Enzymology. Vol. 289. pp. 44β67.
19:
644:
Lam, Pak-Lun; Wu, Yue; Wong, Ka-Leung (30 March 2022).
596:
335:
Common deprotection cocktails for Fmoc during SPPS:
716:
563:
510:
566:Greene's Protective Groups in Organic Synthesis
134:
57:
53:Mechanism of Fmoc protection of amine group
433:
398:
643:
418:
28:fluorenylmethoxycarbonyl protecting group
120:is also a method to install Fmoc group.
48:
18:
92:9-fluorenylmethylsuccinimidyl carbonate
717:
463:"Methods for Removing the Finoc Group"
460:
108:(itself made by reacting Fmoc-Cl with
564:Wuts, P. G. M.; Greene, T.W. (2006).
650:Organic & Biomolecular Chemistry
559:
557:
76:fluorenylmethyloxycarbonyl chloride
13:
106:9-fluorenylmethyloxycarbonyl azide
14:
741:
696:
554:
454:
702:
436:The Journal of Organic Chemistry
143:
82:
637:
590:
545:
504:
427:
392:
386:10.1016/j.molstruc.2007.11.059
374:Journal of Molecular Structure
365:
1:
521:10.1016/s0076-6879(97)89043-x
513:Solid-Phase Peptide Synthesis
406:Canadian Journal of Chemistry
358:
16:Base-labile protecting group
7:
467:Peptide Synthesis Protocols
135:Cleavage & Deprotection
10:
746:
58:Protection & Formation
475:10.1385/0-89603-273-6:17
66:is frequently used as a
609:(126): 104417β104425.
54:
23:
159:N,N-dimethylformamide
52:
22:
725:Biochemistry methods
711:at Wikimedia Commons
266:β HOC(O)NHR + (CH
615:2015RSCAd...5j4417R
448:10.1021/jo00795a005
399:Paquet, A. (1982).
125:reversed phase HPLC
99:-hydroxysuccinimide
662:10.1039/D2OB00070A
623:10.1039/C5RA23441G
574:10.1002/0470053488
279:HOC(O)NHR β CO
232:βOC(O)NHR] β C
114:sodium bicarbonate
55:
24:
730:Protecting groups
707:Media related to
656:(13): 2601β2604.
484:978-1-59259-522-8
442:(22): 3404β3409.
178:βOC(O)NHR + (CH
78:(Fmoc-Cl), e.g.:
44:organic synthesis
737:
706:
690:
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568:. NY: J. Wiley.
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380:(1β3): 187β196.
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68:protecting group
40:protecting group
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413:(8): 976β980.
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104:Reacting with
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144:Roles in SPPS
141:
132:
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603:RSC Advances
602:
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506:
496:, retrieved
466:
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394:
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367:
334:
147:
138:
129:fluorescence
122:
116:and aqueous
110:sodium azide
103:
96:
89:
61:
31:
27:
25:
352:formic acid
244:+ OC(O)NHR
186:NH β (CH
719:Categories
498:2021-10-15
359:References
344:piperazine
311:NH β C
215:βOC(O)NHR]
203:+ [C
155:piperidine
150:N-terminus
686:247175352
670:1477-0539
631:2046-2069
64:carbamate
678:35258068
42:used in
38:-labile
611:Bibcode
539:9353717
493:7894598
350:and 1%
303:+ (CH
161:(DMF).
118:dioxane
34:) is a
684:
676:
668:
629:
580:
537:
527:
491:
481:
220:[C
72:amines
682:S2CID
346:, 1%
283:+ RNH
112:) in
62:Fmoc
709:Fmoc
674:PMID
666:ISSN
627:ISSN
578:ISBN
535:PMID
525:ISBN
489:PMID
479:ISBN
323:N(CH
70:for
36:base
32:Fmoc
26:The
658:doi
619:doi
570:doi
517:doi
471:doi
444:doi
415:doi
382:doi
378:888
348:DBU
342:5%
319:βCH
299:=CH
240:=CH
228:βCH
211:βCH
174:βCH
157:in
721::
680:.
672:.
664:.
654:20
652:.
648:.
625:.
617:.
605:.
601:.
576:.
556:^
533:.
523:.
487:,
477:,
465:,
440:37
438:.
411:60
409:.
403:.
376:.
313:13
293:13
274:NH
257:NH
234:13
222:13
205:13
194:NH
168:13
131:.
101:.
46:.
688:.
660::
633:.
621::
613::
607:5
586:.
572::
541:.
519::
473::
450:.
446::
423:.
417::
388:.
384::
329:5
327:)
325:2
321:2
317:9
315:H
309:5
307:)
305:2
301:2
297:8
295:H
291:C
285:2
281:2
272:5
270:)
268:2
263:2
260:+
255:5
253:)
251:2
242:2
238:8
236:H
230:2
226:8
224:H
213:2
209:8
207:H
200:2
197:+
192:5
190:)
188:2
184:5
182:)
180:2
176:2
172:9
170:H
166:C
97:N
30:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
