Stability of Side‐Chain Protecting Groups in Solid‐Phase Peptide Synthesis
作者:
Bruce W. Erickson,
R. B. Merrifield,
期刊:
Israel Journal of Chemistry
(WILEY Available online 1974)
卷期:
Volume 12,
issue 1‐2
页码: 79-85
ISSN:0021-2148
年代: 1974
DOI:10.1002/ijch.197400009
出版商: WILEY‐VCH Verlag
数据来源: WILEY
摘要:
AbstractThe relative first‐order rates of deprotection of N∈‐benzyloxycarbonyllysine in 2%, 10%, and 50% trifluoroacetic acid in dichloromethane at 20° are 1, 50, and 1000, respectively. The N∈‐2‐chlorobenzyloxycarbonyl group is at least 60 times more stable than the N∈‐benzyloxycarbonyl group under solid‐phase conditions, because no branched peptides (<0.2 mole%) were formed during synthesis of decalysylvaline using Nα‐tert‐butyloxycarbonyl‐N∈‐2‐chlorobenzyloxycarbonyllysine. Since O‐2‐chlorobenzylserine, Nim‐tosylhistidine, Nim‐2,4‐dinitrophenylhistidine and S‐4‐methylbenzylcysteine were completely stable in 50% trifluoroacetic acid–dichloromethane for over 200 h, these side‐chain protecting groups should be suitabl
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