5-thio-α-D-mannopyranosylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 5-thio-α-D-mannopyranosylamine
• 英文别名: 5-Thio-A/B-D-mannopyranosylamine；(2S,3S,4S,5S,6R)-2-amino-6-(hydroxymethyl)thiane-3,4,5-triol
• 化学式: C₆H₁₃NO₄S
• 分子量: 195.24
• InChiKey: FGVRMLQUWLZGLJ-PQMKYFCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  132
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2,3,4,6-penta-O-acetyl-5-thio-α-D-mannopyranose 在 氨 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 49.5h， 生成 5-thio-α-D-mannopyranosylamine
  参考文献：
  名称：

  5-Thio-d-glycopyranosylamines and their amidinium salts as potential transition-state mimics of glycosyl hydrolases: synthesis, enzyme inhibitory activities, X-ray crystallography, and molecular modeling

  摘要：

  The synthesis of new glycosidase inhibitors, namely, the glycosylamines of 5-thioglucose and 5-thiomannose and their corresponding amidinium salts are described. We report also the crystal structures of 5-thio-D-mannopyranosyl amine 1 and 5-thio-D-mannopyranosylamidinium bromide 2 bound in the enzyme active site of Golgi alpha-mannosidase II (GM II). Compounds 1 and 2 have been found to be inhibitors with IC50 values of 0.07 and 0.9 mM, respectively. We also report the docked structures of 5-thin-D-glucopyranosylamine 3 and 5-thio-D-glucopyranosylamidinium bromide 4 in the active site of glucoamylase G2, derived by molecular modeling. Compounds 3 and 4 were found to be inhibitors with K-i values of 0.015 and 0.098 mM, respectively. The results led to conclusions about the nature of the transition state and strategy for the inhibition of glycosyl hydrolases in general. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.021

文献信息

• 5-Thio-d-glycopyranosylamines and their amidinium salts as potential transition-state mimics of glycosyl hydrolases: synthesis, enzyme inhibitory activities, X-ray crystallography, and molecular modeling
  作者：Lizie M. Kavlekar、Douglas A. Kuntz、Xin Wen、Blair D. Johnston、Birte Svensson、David R. Rose、B. Mario Pinto

  DOI：10.1016/j.tetasy.2005.01.021

  日期：2005.3

  The synthesis of new glycosidase inhibitors, namely, the glycosylamines of 5-thioglucose and 5-thiomannose and their corresponding amidinium salts are described. We report also the crystal structures of 5-thio-D-mannopyranosyl amine 1 and 5-thio-D-mannopyranosylamidinium bromide 2 bound in the enzyme active site of Golgi alpha-mannosidase II (GM II). Compounds 1 and 2 have been found to be inhibitors with IC50 values of 0.07 and 0.9 mM, respectively. We also report the docked structures of 5-thin-D-glucopyranosylamine 3 and 5-thio-D-glucopyranosylamidinium bromide 4 in the active site of glucoamylase G2, derived by molecular modeling. Compounds 3 and 4 were found to be inhibitors with K-i values of 0.015 and 0.098 mM, respectively. The results led to conclusions about the nature of the transition state and strategy for the inhibition of glycosyl hydrolases in general. (C) 2005 Elsevier Ltd. All rights reserved.