Document Detail


One-pot protection and activation of amino acids using pentafluorophenyl carbonates.
MedLine Citation:
PMID:  19856278     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Protection of the amino group and activation of the carboxylic acid groups are the most important steps associated with any peptide synthesis protocol; hence, a one-pot process to achieve these is highly desirable. A possible strategy is to use pentafluorophenyl carbonates to simultaneously protect the amino group as a carbamate derivative and activate the carboxylic acid group as a pentafluorophenyl ester. A detailed study is carried out to understand the scope and limitations of this method using five different pentaflurophenyl carbonates. The efficiency of these one-pot reactions depends largely on the nature of the pentafluorophenyl carbonates and also on the nature of the amino acids. Electron deficient and sterically less demanding carbonates reacted faster than the others, whereas amino acids with longer aliphatic side chains gave better yields than more polar amino acids.
Authors:
Ramesh Ramapanicker; Nasir Baig Rashid Baig; Kavita De; Srinivasan Chandrasekaran
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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:  15     ISSN:  1099-1387     ISO Abbreviation:  J. Pept. Sci.     Publication Date:  2009 Dec 
Date Detail:
Created Date:  2009-11-09     Completed Date:  2010-01-11     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9506309     Medline TA:  J Pept Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  849-55     Citation Subset:  IM    
Copyright Information:
(c) 2009 European Peptide Society and John Wiley & Sons, Ltd.
Affiliation:
Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry*
Carbonates / chemistry*
Carboxylic Acids / chemistry*
Fluorine Compounds / chemistry*
Molecular Structure
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Carbonates; 0/Carboxylic Acids; 0/Fluorine Compounds

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