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

Author(s)

Suppo, Jean-Simon ^{[1, 2]} ; de Sant'Ana, Danilo Pereira ^{[3, 1, 2]} ; Dias, Luiz Carlos ^[3] ; de Figueiredo, Renata Marcia ^{[1, 2]} ; Campagne, Jean-Marc ^{[1, 2]}

Affiliation

^[1] UMR 5253 CNRS UM2 UM1 ENSCM, Inst Charles Gerhardt Montpellier, F-34296 Montpellier 5 - France

^[2] Ecole Natl Super Chim, F-34296 Montpellier 5 - France

^[3] Univ Estadual Campinas, Inst Chem, UNICAMP, BR-13084971 Campinas, SP - Brazil

• Document type: Journal article
• Source: SYNTHESIS-STUTTGART; v. 46, n. 22, p. 3075-3084, NOV 2014.
• Web of Science Citations: 0

Abstract

An efficient and practical procedure for the free -carboxylic acid esterification of amino acid residues with -(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 -amino moiety and side chains or the optical integrity at the -position of the amino acid residues. Examples of their use in peptide synthesis are also illustrated. (AU)

• FAPESP's process: 12/11220-9 - Synthesis of anhydride fragment from tautomycetin
• Grantee: Danilo Pereira de Sant'Ana
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate