174193-56-7Relevant academic research and scientific papers
Synthesis and conformational analysis of the Amadori compound N-(2,3:4,5-di-O-isopropylidene-1-deoxy-β-D-fructopyranos-1-yl)-L-tyrosine benzyl ester
Kojic-Prodic, Biserka,Milinkovic, Vjekoslav,Kidric, Jurka,Pristovsek, Primoz,Horvat, Stefica,Jakas, Andreja
, p. 21 - 40 (1995)
The title compound, a precursor in the synthesis of other analogues of Amadori type, was prepared and characterized by X-ray structure analysis and NMR spectroscopy.The molecule crystallized in the orthorhombic space group P21212sub
Synthesis and 13C NMR investigation of novel Amadori compounds (1-amino-1-deoxy-D-fructose derivatives) related to the opioid peptide, leucine-enkephalin
Jakas, Andreja,Horvat, Stefica
, p. 789 - 794 (2007/10/03)
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%).
