Side reactions of monoaminodicarboxylic acids in peptide synthesis
作者:
BOGDAN LIBEREK,
REGINA KASPRZYKOWSKA,
期刊:
International Journal of Peptide and Protein Research
(WILEY Available online 1988)
卷期:
Volume 31,
issue 1
页码: 58-62
ISSN:0367-8377
年代: 1988
DOI:10.1111/j.1399-3011.1988.tb00006.x
出版商: Blackwell Publishing Ltd
关键词: δ‐amide to nitrile dehydration during activation and coupling;homoglutamine side reactions;monoaminodicarboxylic acid side reactions;proximity effects;side reactions in peptide synthesis
数据来源: WILEY
摘要:
N‐benzyloxycarbonyl‐l‐homoglutamine was studied to answer the question whether or not there is any tendency for the dehydration of the δ‐carboxamide group during activation and coupling. Only a minor conversion to nitrile by‐products was found in the activation of the α‐carboxyl group and formation of peptide bond with the help of dicyclohexylcarbodiimide. Addition ofN‐hydroxybenzotriazole to the reacting mixture eliminates the side chain dehydration reaction. The dehydration reaction is also overcome by protection of the side chain carboxamide with the benzyloxycarbonylcarbam
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