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Issue 5, 1998
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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.

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Article type: Paper
DOI: 10.1039/A707509J
J. Chem. Soc., Perkin Trans. 1, 1998, 909-914

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    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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