The chemistry of the collagen cross-links. A convenient synthesis of the reduction products of several collagen cross-links and cross-link precursors.
New synthetic routes to the reduction products of several collagen cross-links and cross-link precursors are described. By the use of these routes hydroxynorleucine, 5,6-dihydroxynorleucine, hydroxylysinonorleucine and hydroxylysinohydroxynorleucine can be synthesized via one common synthetic intermediate. The synthetic routes provide a convenient source of these unusual amino acids, as well as confirming the structure of hydroxylysinohydroxynorleucine and the other lysine-derived residues found in borohydride-reduced collagens.
D000596:Amino Acids / Q000032:analysis; D000641:Ammonia / Q000032:analysis; D003094:Collagen / Q000032:analysis / Q000138:chemical synthesis*; D005557:Formaldehyde / Q000032:analysis; D006900:Hydroxylation; D008239:Lysine; D008274:Magnesium; D013058:Mass Spectrometry; D009646:Norleucine; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis; D010504:Periodic Acid
D000596:Amino Acids; D010455:Peptides; D010504:Periodic Acid; D005557:Formaldehyde; D000641:Ammonia; D009646:Norleucine; D003094:Collagen; D008274:Magnesium; D008239:Lysine