Efficient and Practical Procedure for the Esterification of the Free α-Carboxylic Acid of Amino Acid Residues with β-(Trimethylsilyl)ethoxymethyl Chloride and Triisopropylsilyl Chloride

Jean-Simon Suppo; Danilo Pereira de Sant’Ana; Luiz Carlos Dias; Renata Marcia de Figueiredo; Jean-Marc Campagne

doi:10.1055/s-0034-1379004

Synthesis, Table of Contents

Synthesis 2014; 46(22): 3075-3084
DOI: 10.1055/s-0034-1379004

paper

Efficient and Practical Procedure for the Esterification of the Free α-Carboxylic Acid of Amino Acid Residues with β-(Trimethylsilyl)ethoxymethyl Chloride and Triisopropylsilyl Chloride

Jean-Simon Suppo

^aInstitut Charles Gerhardt Montpellier, UMR 5253 CNRS-UM2-UM1-ENSCM; Ecole Nationale Supérieure de Chimie, 8 Rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France Fax: +33(4)67144322 Email: renata.marcia_de_figueiredo@enscm.fr

,

Danilo Pereira de Sant’Ana

^aInstitut Charles Gerhardt Montpellier, UMR 5253 CNRS-UM2-UM1-ENSCM; Ecole Nationale Supérieure de Chimie, 8 Rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France Fax: +33(4)67144322 Email: renata.marcia_de_figueiredo@enscm.fr

^bInstitute of Chemistry, University of Campinas, UNICAMP, P. O. Box 6154, 13084-971 Campinas-SP, Brazil

,

Luiz Carlos Dias

^bInstitute of Chemistry, University of Campinas, UNICAMP, P. O. Box 6154, 13084-971 Campinas-SP, Brazil

,

Renata Marcia de Figueiredo*

^aInstitut Charles Gerhardt Montpellier, UMR 5253 CNRS-UM2-UM1-ENSCM; Ecole Nationale Supérieure de Chimie, 8 Rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France Fax: +33(4)67144322 Email: renata.marcia_de_figueiredo@enscm.fr

,

Jean-Marc Campagne*

^aInstitut Charles Gerhardt Montpellier, UMR 5253 CNRS-UM2-UM1-ENSCM; Ecole Nationale Supérieure de Chimie, 8 Rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France Fax: +33(4)67144322 Email: renata.marcia_de_figueiredo@enscm.fr

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Abstract

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Dedicated to Professor Dr. Dieter Enders

Abstract

An efficient and practical procedure for the free α-carboxylic acid esterification of amino acid residues with β-(trimethylsilyl)ethoxymethyl chloride and triisopropylsilyl chloride is described. The reaction takes place under mild conditions and the expected protected amino acids are obtained in good to excellent yields. Our method provides a useful alternative for the C-terminal carboxylic acid protection of amino acids and peptides. Moreover, the removal of such protection was also achieved under mild conditions, without affecting either the other protecting groups at the α-amino moiety and side chains or the optical integrity at the α-position of the amino acid residues. Examples of their use in peptide synthesis are also illustrated.

Key words

amino acids - protecting groups - carboxylic acids - synthetic methodology - peptides - organic synthesis

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References

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