Fluorescent properties of amino acids labeled with ortho-aminobenzoic acid

Fluorescent properties of amino acids labeled with ortho-aminobenzoic acid

Autor Ito, A. S. Google Scholar
Turchiello, RDF Google Scholar
Hirata, I. Y. Google Scholar
Cezari, MHS Google Scholar
Meldal, M. Google Scholar
Juliano, L. Google Scholar
Instituição Universidade Federal de São Paulo (UNIFESP)
Universidade de São Paulo (USP)
Dept Chem
Resumo ortho-Aminobenzoic acid (Abz) has been used as a convenient fluorescent donor group in internally quenched fluorescent peptides, which are employed as substrates for several proteolytic enzymes. As Abz is usually bound to the N-amino terminal of these peptides, it is of interest to investigate the Abz group fluorescent properties bound to different amino acids. We report in this article the optical absorption and fluorescent properties, in aqueous media, of Abz bound to the alpha-amino group of Ala, Gly, Leu, ne, Val, Pro, Phe, Arg, Glu, Met, Asn, Tyr, and Trp, with monomethyl-amidated alpha-carboxyl group, in order to explore the origin of the drastic reduction of Abz attached to N-alpha amino group of prolyl-peptides, we also examined the fluorescence properties of Abz-NHCH3, Abz-N(CH3)(2), and Abz-pyrrolidine. Molecular dynamics simulation and NMR data indicated a lack of periplanarity of the Abz-dimethylamide, which could be the origin of low fluorescence quantum yield of Abz-prolyl-peptides. (C) 1998 John Wiley & Sons, Inc.
Palavra-chave ortho-aminobenzoylamino acids
fluorescence
protease
peptide
peptide synthesis
Idioma Inglês
Data de publicação 1998-01-01
Publicado em Biospectroscopy. W Sussex: John Wiley & Sons Ltd, v. 4, n. 6, p. 395-402, 1998.
ISSN 1075-4261 (Sherpa/Romeo, fator de impacto)
Publicador Wiley-Blackwell
Extensão 395-402
Fonte http://dx.doi.org/10.1002/(SICI)1520-6343(1998)4:6<395
Direito de acesso Acesso restrito
Tipo Artigo
Web of Science WOS:000077234300004
Endereço permanente http://repositorio.unifesp.br/handle/11600/25836

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