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Urethane‐protected α‐amino acid N‐carboxyanhydrides and peptide synthesis
Author(s) -
Fuller William D.,
Goodman Murray,
Naider Fred R.,
Zhu YunFei
Publication year - 1996
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/(sici)1097-0282(1996)40:2<183::aid-bip1>3.0.co;2-s
Subject(s) - chemistry , pyridine , peptide synthesis , peptide , protecting group , condensation , amino acid , combinatorial chemistry , organic chemistry , polymer chemistry , biochemistry , alkyl , physics , thermodynamics
The preparation, physical properties and analytical data are reported for seventy urethane‐protected (Boc, Cbz, FMOC) amino acid N‐carboxyanhydrides (UNCAs). Most of the UNCAs are crystalline and the X‐ray diffraction patterns for several of these are described. UNCAs are stable to routine laboratory manipulations and can be stored for extended periods of time (1–2 years at below 0°C). Most are completely stable to the conditions commonly employed for peptide synthesis. The correct choice of base is key for the successful introduction of urethane protecting groups into NCAs. N‐Methylmorpholine is used for the introduction of FMOC, Cbz or Boc from the chloroformates, and pyridine is used for the introduction of the Boc group from Boc anhydride. UNCAs represent a unique class of preactivated, isolable and stable amino acid derivatives that generate no side products or co‐products, other than CO 2 , during condensation reactions. The application of UNCAs in peptide synthesis in both solid phase and in solution is reviewed in detail. © 1996 John Wiley & Sons, Inc.