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A novel pyrroleninone cross-link from bovine dentine

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Author: Kleter, G.A. · Damen, J.J.M. · Kettenes-Bosch, J.J. van den · Bank, R.A. · Koppele, J.M. te · Veraart, J.R. · Cate, J.M. ten
Institution: Instituut CIVO-Toxicologie en Voeding TNO
Source:Biochimica et Biophysica Acta - General Subjects, 2, 1381, 179-190
Identifier: 234544
doi: DOI:10.1016/S0304-4165(98)00027-0
Keywords: Nutrition · Collagen · Cow · Cross-linking amino acid · Dentine · Amino acid · Hydroxylysine · Pyridinoline · Pyridone derivative · Reagent · Cattle · Chemical structure · Cross linking · Dentin · Gel permeation chromatography · Ion exchange chromatography · Nonhuman · Nuclear magnetic resonance spectroscopy · Priority journal · Amino Acids · Animals · Cattle · Chromatography, Ion Exchange · Collagen · Cross-Linking Reagents · Dentin · Electrophoresis, Capillary · Magnetic Resonance Spectroscopy · Mass Spectrometry · Molecular Structure · Pyrroles


The aim was to identify suspect collagen cross-links in dentine, eluting close to known cross-links in ion-exchange HPLC. Bovine tooth roots as source of dentine were powdered, demineralised, reduced, and acid-hydrolysed. Cross-linking amino acids were isolated from the acid hydrolysate by size exclusion, adsorption, and sequential ion exchange chromatography. In addition to dihydroxylysinonorleucine and hydroxylysylpyridinoline, an unknown cross-link was isolated (V-2). The ultraviolet, mass, and nuclear magnetic resonance spectra support the proposed structure of V-2, a trimeric amino acid with a pyrroleninone nucleus. Copyright (C) 1998 Elsevier Science B.V.