β-methyl-D-galactopyranosiduronic acid | 5241-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-methyl-D-galactopyranosiduronic acid
• 英文别名: O¹-methyl-β-D-galactopyranuronic acid；O¹-Methyl-β-D-galactopyranuronsaeure；(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methoxyoxane-2-carboxylic acid
• CAS: 5241-02-1
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: BOFXVYGDIRCHEQ-SKYANUQHSA-N

物化性质

• 沸点：
  461.0±45.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  β-methyl-D-galactopyranosiduronic acid 在 苯磺酰胺 、 β(1-4)gal-t 、 sodium cacodylate buffer 、 sodium methylate 、 O-Benzotriazol-1-yl-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate 、 三乙胺 、 magnesium chloride 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->4)-2-deoxy-2-(methyl-β-D-galactohexopyranosyluronamide)-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl-transferase catalyzed assemblage of sialyl-lewis x -saccharopeptides

  摘要：

  A series of glycohexopyranuronic acids are coupled to glucosamines to give 'disaccharides' which have the natural N-acetyl group of the glcNAc-moiety replaced by various sugar acids (-->saccharopeptides). These saccharopeptides are surprisingly good substrates for beta(1-4)galactosyl-transferase, alpha(2-3)sialyl-transferase, and fucosyl-transferase VI. The enzymes transfer successively galactose, sialic acid, and fucose from the corresponding donors onto these acceptor substrates-despite the far reaching alterations-regio- and stereospecifically in the expected manner to yield a new class of compounds, the sialyl-Lewis(x)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00107-2
• 作为产物：
  描述：

  半乳糖醛酸 在 盐酸 、 barium dihydroxide 、 水 作用下， 生成 β-methyl-D-galactopyranosiduronic acid
  参考文献：
  名称：

  Smolenski; Cichocki, Collection of Czechoslovak Chemical Communications, 1932, vol. 4, p. 500,502

  摘要：

  DOI：

文献信息

• Formation of Uronic Acid by Galactose Oxidase
  作者：Shuichi Matsumura、Akihiro Kuroda、Norihiko Higaki、Yukari Hiruta、Sadao Yoshikawa

  DOI：10.1246/cl.1988.1747

  日期：1988.10.5

  The C-6 hydroxymethyl group of methyl d-galactopyranoside and oligosaccharides containing d-galactopyranosyl residues were found to be oxidized with oxygen by galactose oxidase to the corresponding carboxyl group via an aldehyde intermediate.

  甲基d-半乳糖吡喃糖苷和含有d-半乳糖吡喃糖残基的寡糖的C-6羟甲基组被发现可以在半乳糖氧化酶的作用下，与氧气反应，被氧化为相应的羧酸基团，经过一个醛的中间体。
• 289. The synthesis of conjugated hexuronic acids
  作者：C. A. Marsh

  DOI：10.1039/jr9520001578

  日期：——
• Ehrlich; Guttmann, Chemische Berichte, 1933, vol. 66, p. 220,225
  作者：Ehrlich、Guttmann

  DOI：——

  日期：——
• Synthesis of methyl ethers of methyl (methyl ?-D-galactopyranosid)uronate
  作者：E. V. Evtushenko、Yu. S. Ovodov

  DOI：10.1007/bf00602452

  日期：——
• Glycosyltransferase catalyzed assemblage of sialyl-Lewisa-saccharopeptides
  作者：Gabi Baisch、Reinhold Öhrlein

  DOI：10.1016/s0008-6215(98)00229-8

  日期：1998.11

  A series of methyl hexopyranosiduronic acids are coupled to type I disaccharide amines to give 'trisaccharides' which have the natural N-acetyl group of the type I disaccharides replaced by uronic acids (--> saccharopeptides). These saccharopeptides are surprisingly good substrates for alpha-2,3-sialyltransferase and fucosyltransferase III. The enzymes transfer N-acetylneuraminic acid and fucose, respectively, onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to yield sialyl-Lewis(a)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.