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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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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]
Total Authors: 5
[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
Total Affiliations: 3
Document type: Journal article
Source: SYNTHESIS-STUTTGART; v. 46, n. 22, p. 3075-3084, NOV 2014.
Web of Science Citations: 0

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