(E)-[(4'R,5'R,6'S)-6'-acetamido-4',5'-dihydroxy-3'-hydroxymethylcyclohex-2'-enylidene]acetic acid | 1091630-18-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-[(4'R,5'R,6'S)-6'-acetamido-4',5'-dihydroxy-3'-hydroxymethylcyclohex-2'-enylidene]acetic acid
• 英文别名: (2E)-2-[(4R,5R,6S)-6-acetamido-4,5-dihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-ylidene]acetic acid
• CAS: 1091630-18-0
• 化学式: C₁₁H₁₅NO₆
• 分子量: 257.243
• InChiKey: NSBPEEXFDHIWGM-ZPJUIYLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-{ethyl [(4'R,5'R,6'S)-6'-acetamido-4',5'-diacetoxy-3'-acetoxymethylcyclohex-2'-enylidene]acetate} 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以75%的产率得到(E)-[(4'R,5'R,6'S)-6'-acetamido-4',5'-dihydroxy-3'-hydroxymethylcyclohex-2'-enylidene]acetic acid
  参考文献：
  名称：

  The synthesis and biological evaluation of some carbocyclic analogues of PUGNAc

  摘要：

  The synthesis of some analogues of O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate, PUGNAc, an inhibitor of beta-N-acetylglucosaminidases, is described. The analogues were tested against a range of beta-N-acetylglucosaminidases to establish any biological activity. As well, the analogues were tested as inhibitors of a uridine diphosphate-N-acetyl-D-glucosamine: polypeptidyl transferase, OGT, a critical protein involved in the post-translational modification of nuclear and cytosolic proteins by N-acetyl-D-glucosamine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.08.012

文献信息

• The synthesis and biological evaluation of some carbocyclic analogues of PUGNAc
  作者：Adrian Scaffidi、Keith A. Stubbs、David J. Vocadlo、Robert V. Stick

  DOI：10.1016/j.carres.2008.08.012

  日期：2008.11

  The synthesis of some analogues of O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate, PUGNAc, an inhibitor of beta-N-acetylglucosaminidases, is described. The analogues were tested against a range of beta-N-acetylglucosaminidases to establish any biological activity. As well, the analogues were tested as inhibitors of a uridine diphosphate-N-acetyl-D-glucosamine: polypeptidyl transferase, OGT, a critical protein involved in the post-translational modification of nuclear and cytosolic proteins by N-acetyl-D-glucosamine. (C) 2008 Elsevier Ltd. All rights reserved.