化学
旋转
吡喃糖
立体化学
脑啡肽
呋喃糖
阿玛多利重排
互变异构体
药物化学
有机化学
生物化学
糖基化
类阿片
戒指(化学)
受体
作者
Andreja Jakas,Ŝtefica Horvat
出处
期刊:Journal of the Chemical Society
日期:1996-01-01
卷期号: (5): 789-794
被引量:16
摘要
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 D2O 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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