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J Chromatogr B Biomed Sci Appl ; 739(2): 273-80, 2000 Mar 10.
Article in English | MEDLINE | ID: mdl-10755371

ABSTRACT

Allysine is the most important precursor of physiologically essential cross-links formation in collagen and elastin and is formed by enzymatic oxidative deamination of lysine residues. Because it is a highly reactive aldehyde, many cross-linking amino acid residues may arise from its reaction with other allysine residues or lysine or even histidine residues. We purified and isolated an allysine bisphenol derivative, 1-amino-1-carboxy-5,5-bis-p-hydroxyphenylpentane (ACPP), from the reaction products of phenol and allysine residue of bovine ligamentum nuchae by acid hydrolysis in 6 M HCl. The structure of ACPP was verified by UV, fast atom bombardment-MS, 1H- and 13C-nuclear magnetic resonance spectroscopies. The optimal reaction condition for ACPP synthesis accompanied by hydrolysis of such proteins was investigated and an ion-paired high-performance liquid chromatographic method for determination of allysine as ACPP was also developed.


Subject(s)
2-Aminoadipic Acid/analogs & derivatives , Chromatography, High Pressure Liquid/methods , Phenols/chemistry , 2-Aminoadipic Acid/analysis , 2-Aminoadipic Acid/chemistry , Animals , Cattle , Reproducibility of Results , Spectrophotometry, Ultraviolet
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