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Volume 271, Number 24, Issue of June 14, 1996 pp. 14271-14279
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.

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Nitrosation of Tryptophan Residue(s) in Serum Albumin and Model Dipeptides
BIOCHEMICAL CHARACTERIZATION AND BIOACTIVITY

(Received for publication, January 22, 1996, and in revised form, April 2, 1996)

Ying-Yi Zhang ^§ , Ai-Ming Xu , Miguel Nomen ^§ , Mary Walsh ^¶ , John F. Keaney Jr. and Joseph Loscalzo

From the  Whitaker Cardiovascular Institute, Evans Department of Medicine, and Departments of  Biochemistry, and ^¶ Biophysics, Boston University School of Medicine, Boston, Massachusetts 02118-2394 and the ^§ Department of Cell Biology, University of Medicine and Dentistry of New Jersey, Stratford, New Jersey 08084-1489

Nitrosation of bovine serum albumin with acidified NaNO₂ was compared to that of carboxymethyl-bovine serum albumin in which the thiol group is covalently blocked. Differential ultraviolet-visible (UV-Vis) spectroscopy and a modified Saville assay indicated that a non-cysteine residue(s) in carboxymethyl-bovine serum albumin was nitrosated. The nitrosated carboxymethyl-bovine serum albumin exhibited similar vasorelaxation activity as that observed with nitrosated bovine serum albumin. Identification of the nitrosated non-cysteine residue(s) was studied using 16 model dipeptides, each of which contained a glycyl residue and a variable residue. Using photolysis-chemiluminescence analysis, modified Saville assay, differential UV-Vis spectroscopy, and bioassays, L-glycyl-L-tryptophan (Gly-Trp) was found to be the only dipeptide that underwent significant nitrosation under these conditions. Liquid chromatography-UV-Vis spectroscopy-mass spectrometry showed that the NO group was attached to the indole nitrogen of tryptophan. Nitrosated Gly-Trp exhibited dose-dependent vasorelaxation and platelet inhibiting activity with apparent EC₅₀ values of 1.1 ± 0.3 and 3.5 ± 0.9 µM, respectively. Because N-nitroso-Gly-Trp does not release NO radical via spontaneous homolytic N-NO bond fission nor freely diffuse through cellular membranes, the ability of this compound to induce NO-like biological effects suggests the existence of a (membrane-associated) transnitrosation system that facilitates delivery of -NO to its specific biologic target(s).

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