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Synthesis of the very acid‐sensitive Fmoc‐Cys(Mmt)‐OH and its application in solid‐phase peptide synthesis

 

作者: KLEOMENIS BARLOS,   DIMITRIOS GATOS,   OLGA HATZI,   NICOLE KOCH,   SOFIA KOUTSOGIANNI,  

 

期刊: International Journal of Peptide and Protein Research  (WILEY Available online 1996)
卷期: Volume 47, issue 3  

页码: 148-153

 

ISSN:0367-8377

 

年代: 1996

 

DOI:10.1111/j.1399-3011.1996.tb01338.x

 

出版商: Blackwell Publishing Ltd

 

关键词: cysteine deprotection;cysteine oxidation;4‐methoxytrityl protection;solid‐phase peptide synthesis;somatostatin synthesis

 

数据来源: WILEY

 

摘要:

S‐4‐methoxytrityl cysteine was synthesized and converted into the corresponding Fmoc‐Cys(Mmt)‐OH by its reaction with Fmoc‐OSu. As compared to the corresponding Fmoc‐Cys(Trt)‐OH, theS‐Mmt‐function was found to be considerably more acid labile. QuantitativeS‐Mmt‐removal occurs selectively in the presence of groups of thetertbutyl type andS‐Trt by treatment with 0.5–1.0% TFA. The new derivative was successfully utilized in the SPPS of Tyr1‐somatostatin on 2‐chlorotrityl resin. In this synthesis groups of the Trt‐type were exclusively used for amino acid side‐chain protection. Quantitative cleavage from the resin and complete deprotection was performed by treatment with 3% TFA in DCM–TES (95:5) for 30 min at RT. We observed no reduction of tryptophan under

 

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