One-pot protection and activation of amino acids using pentafluorophenyl carbonates

Ramapanicker, Ramesh ; Baig, Nasir Baig Rashid ; De, Kavita ; Chandrasekaran, Srinivasan (2009) One-pot protection and activation of amino acids using pentafluorophenyl carbonates Journal of Peptide Science, 15 (12). pp. 849-855. ISSN 1075-2617

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/psc.118...

Related URL: http://dx.doi.org/10.1002/psc.1187

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to European Peptide Society.
Keywords:Carbonates; Protecting Groups; Amino Acids; One-pot Reactions; Peptide Synthesis; Active Esters
ID Code:7303
Deposited On:25 Oct 2010 11:53
Last Modified:01 Feb 2011 08:32

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