Fluorescent properties of amino acids labeled with ortho-aminobenzoic acid

Fluorescent properties of amino acids labeled with ortho-aminobenzoic acid

Author 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
Institution Universidade Federal de São Paulo (UNIFESP)
Universidade de São Paulo (USP)
Dept Chem
Abstract 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.
Keywords ortho-aminobenzoylamino acids
fluorescence
protease
peptide
peptide synthesis
Language English
Date 1998-01-01
Published in Biospectroscopy. W Sussex: John Wiley & Sons Ltd, v. 4, n. 6, p. 395-402, 1998.
ISSN 1075-4261 (Sherpa/Romeo, impact factor)
Publisher Wiley-Blackwell
Extent 395-402
Origin http://dx.doi.org/10.1002/(SICI)1520-6343(1998)4:6<395
Access rights Closed access
Type Article
Web of Science ID WOS:000077234300004
URI http://repositorio.unifesp.br/handle/11600/25836

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