2-乙酰氨基葡萄烯糖 | 10293-59-1

• 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
• 中文名称: 2-乙酰氨基葡萄烯糖
• 英文名称: 2-acetamidoglucal
• 英文别名: N-acetyl-D-glucal；2-Acetamido-1,2-dideoxy-D-arabino-hex-1-enopyranose；N-[(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-5-yl]acetamide
• CAS: 10293-59-1
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: LKFJQOCOGNNTCY-BWZBUEFSSA-N

物化性质

• 沸点：
  488.1±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到2-乙酰氨基葡萄烯糖
  参考文献：
  名称：

  Characterizing non-hydrolyzing Neisseria meningitidis serogroup A UDP-N-acetylglucosamine (UDP-GlcNAc) 2-epimerase using UDP-N-acetylmannosamine (UDP-ManNAc) and derivatives

  摘要：

  Neisseria meningitidis serogroup A non-hydrolyzing uridine 5'-diphosphate-N-acetylglucosamine (UDP-GlcNAc) 2-epimerase (NmSacA) catalyzes the interconversion between UDP-GlcNAc and uridine 5'-diphosphate-N-acetylmannosamine (UDP-ManNAc). It is a key enzyme involved in the biosynthesis of the capsular polysaccharide [-6ManNAc alpha 1-phosphate-](n) of N. meningitidis serogroup A, one of the six serogroups (A, B, C, W-135, X, and Y) that account for most cases of N. meningitidis-caused bacterial septicemia and meningitis. N. meningitidis serogroup A is responsible for large epidemics in the developing world, especially in Africa. Here we report that UDP-ManNAc could be used as a substrate for C-terminal His(6)-tagged recombinant NmSacA (NmSacA-His(6)) in the absence of UDP-GlcNAc. NmSacA-His(6) was activated by UDP-GlcNAc and inhibited by 2-acetamidoglucal and UDP. Substrate specificity study showed that NmSacA-His(6) could tolerate several chemoenzymatically synthesized UDP-ManNAc derivatives as substrates although its activity was much lower than non-modified UDP-ManNAc. Homology modeling and molecular docking revealed likely structural determinants of NmSacA substrate specificity. This is the first detailed study of N. meningitidis serogroup A UDP-GlcNAc 2-epimerase. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.10.016

文献信息

• Means and methods for producing Neisseria meningitidis capsular polysaccharides of low dispersity
  申请人：Medizinische Hochschule Hannover

  公开号：US10407703B2

  公开（公告）日：2019-09-10

  The present invention relates to in vitro methods for producing Neisseria meningitidis capsular polysaccharides which have a defined length. The present invention also relates to compositions comprising at least one capsule polymerase, at least one donor carbohydrate and at least one acceptor carbohydrate, wherein the ratio of donor carbohydrate to acceptor carbohydrate is a ratio from 10:1 to 400:1. Moreover, the present invention provides truncated versions of the capsule polymerases of Neisseria meningitidis serogroups A and X. Also provided herein are pharmaceuticals, in particular vaccines, comprising the synthetic capsular polysaccharides of Neisseria meningitidis which have a defined length. Furthermore, the invention provides for methods for the production of said vaccines.

  本发明涉及生产具有规定长度的脑膜炎奈瑟氏菌荚膜多糖的体外方法。本发明还涉及包含至少一种胶囊聚合酶、至少一种供体碳水化合物和至少一种受体碳水化合物的组合物，其中供体碳水化合物与受体碳水化合物的比例为 10:1 至 400:1。此外，本发明还提供了脑膜炎奈瑟菌 A 和 X 血清群胶囊聚合酶的截短版本。本发明还提供了包含脑膜炎奈瑟菌合成胶囊多糖的药物，特别是疫苗，这些胶囊多糖具有确定的长度。此外，本发明还提供了生产上述疫苗的方法。
• EP0532530A4
  申请人：——

  公开号：EP0532530A4

  公开（公告）日：1993-05-26
• DERIVATIVES OF 6-AMINOOCTAHYDROINDOLIZINETRIOL
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0532530B1

  公开（公告）日：1997-07-23
• MEANS AND METHODS FOR PRODUCING NEISSERIA MENINGITIDIS CAPSULAR POLYSACCHARIDES OF LOW DISPERSITY
  申请人：Medizinische Hochschule Hannover

  公开号：EP3131576A2

  公开（公告）日：2017-02-22
• US5079254A
  申请人：——

  公开号：US5079254A

  公开（公告）日：1992-01-07