Tetrahedron

Use of N-trifluoroacetyl-protected amino acid chlorides in peptide coupling reactions with virtually complete preservation of stereochemistry

…, A Rusowicz, S Swaminathan, J Livshitz, EJ Delaney

Index: Jass, Paul A.; Rosso, Victor W.; Racha, Saibaba; Soundararajan, Nachimuthu; Venit, John J.; Rusowicz, Andrew; Swaminathan, Shankar; Livshitz, Julia; Delaney, Edward J. Tetrahedron, 2003 , vol. 59, # 45 p. 9019 - 9029

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Citation Number: 12

Abstract

The use of protected amino acid chlorides for peptide coupling reactions has long been avoided due to the extensive racemization that commonly occurs during either the acid chloride formation or the coupling reaction itself. Conditions are described which allow N- trifluoroacetyl-protected amino acid chlorides to be generated in high purity and with high retention of stereochemical integrity. Control of temperature is the predominant factor in ...