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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

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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Autor(es):
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]
Número total de Autores: 5
Afiliação do(s) autor(es):
[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
Número total de Afiliações: 3
Tipo de documento: Artigo Científico
Fonte: SYNTHESIS-STUTTGART; v. 46, n. 22, p. 3075-3084, NOV 2014.
Citações Web of Science: 1
Resumo

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)

Processo FAPESP: 12/11220-9 - Síntese do fragmento anidrido da tautomicetina
Beneficiário:Danilo Pereira de Sant'Ana
Linha de fomento: Bolsas no Exterior - Estágio de Pesquisa - Doutorado