Document Detail

The application of an aryl hydrazine linker prevents beta-elimination side products in the SPPS of C-terminal cysteine peptides.
MedLine Citation:
PMID:  20474043     Owner:  NLM     Status:  MEDLINE    
Solid-phase synthesis allows for the preparation of some complex cysteine-containing peptides with both a high yield and purity. However, side reactions during chain elongation such as modification of amino acid residues have been found in C-terminal cysteine peptides. We identified 3-(1-piperidinyl)-alanine peptides, corroborated the mechanism of the side reaction, and introduced an efficient approach for the Fmoc-based synthesis of C-terminal cysteine peptides using an aryl hydrazine linker.
Shuaijian Ni; Huibin Zhang; Wenlong Huang; Jinpei Zhou; Hai Qian; Wei Chen
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of peptide science : an official publication of the European Peptide Society     Volume:  16     ISSN:  1099-1387     ISO Abbreviation:  J. Pept. Sci.     Publication Date:  2010 Jun 
Date Detail:
Created Date:  2010-05-17     Completed Date:  2010-08-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9506309     Medline TA:  J Pept Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  309-13     Citation Subset:  IM    
Copyright Information:
(c) 2010 European Peptide Society and John Wiley & Sons, Ltd.
Center for Drug Discovery, China Pharmaceutical University, Nanjing, China.
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MeSH Terms
Alanine / chemistry
Amino Acid Sequence
Cysteine / chemistry*
Hydrazines / chemistry*
Molecular Sequence Data
Molecular Structure
Peptides* / chemical synthesis,  chemistry
Reg. No./Substance:
0/Hydrazines; 0/Peptides; 302-01-2/hydrazine; 52-90-4/Cysteine; 56-41-7/Alanine

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