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Synthesis and 13C NMR investigation of novel Amadori compounds (1-amino-1-deoxy-D-fructose derivatives) related to the opioid peptide, leucine-enkephalin

DOI: 10.1039/P29960000789

Source and publish data:

Journal of the Chemical Society. Perkin Transactions 2 (2001) p. 789 - 794 (1996)

Update date:2022-07-31

Topics:

Authors:

Jakas, AndrejaJakas, Andreja

Horvat, SteficaHorvat, Stefica

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Article abstract of DOI:10.1039/P29960000789

The N-(1-deoxy-D-fructos-1-yl) derivatives (Amadori compounds) of the endogenous opioid pentapeptide, leucine-enkephalin (11), leucine-enkephalin methyl ester (12) and of structurally related peptides (9, 10) are synthesized. The equilibrium compositions of the prepared Amadori compounds 9-12 in D 2O and [2H6]DMSO are determined using 13C NMR spectroscopy. In water, the β-pyranose, α-furanose and β-furanose forms are detected, the β-pyranose tautomer being the most abundant at equilibrium (67-75%). The α-pyranose form and open-chain keto form are not detected. In dimethyl sulfoxide, the equilibrium compositions of 9-12 are markedly shifted towards a higher proportion of furanose forms, amounting to two-thirds of the mixture. In addition to the α- and β-furanoses and β-pyranose tautomers, DMSO solutions of compounds 9-12 contain at equilibrium a relatively high proportion of the acyclic hydrate (gem-diol) form (ca. 10%).

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