Issue 5, 1998

Intramolecular rearrangement of the monosaccharide esters of an opioid pentapeptide: formation and identification of novel Amadori compounds related to fructose and tagatose

Abstract

Intramolecular rearrangements leading to Amadori adducts 4 and 5 from monosaccharide esters 1–3 in which either D-glucose, D-mannose or D-galactose is linked through its C-6 hydroxy group to the C-terminal carboxy group of the endogenous opioid pentapeptide leucine-enkephalin (H-Tyr-Gly-Gly-Phe-Leu-OH) are reported. The formation of bicyclic compounds 4 and 5 from the corresponding monosaccharide esters is much faster than formation of the Amadori product from the parent free sugar and leucine-enkephalin. Bicyclic ketoses 4 and 5 are each transformed by hydrolysis into the corresponding 1-amino-1-deoxy-D-fructose (6) and -D-tagatose (7) Amadori products of leucine-enkephalin, indistinguishable by their physical and spectroscopic data from compounds 6 and 7 obtained by independent syntheses. The equilibrium compositions of the prepared Amadori compounds 4–7 in aqueous solutions have been determined by 13C NMR spectroscopy.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1998, 909-914

Intramolecular rearrangement of the monosaccharide esters of an opioid pentapeptide: formation and identification of novel Amadori compounds related to fructose and tagatose

Š. Horvat, M. Roščić, L. Varga-Defterdarović and J. Horvat, J. Chem. Soc., Perkin Trans. 1, 1998, 909 DOI: 10.1039/A707509J

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