methyl β-L-galactopyranosiduronic acid | 219483-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-L-galactopyranosiduronic acid
• 英文别名: (2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methoxyoxane-2-carboxylic acid
• CAS: 219483-90-6
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: BOFXVYGDIRCHEQ-WKYFMQCPSA-N

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：

  methyl β-L-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 76.0h， 生成 C₂₉H₅₁NO₁₈
  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：

  Methyl-D-galactopyranoside 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium bromide 作用下， 以 水 为溶剂， 以74%的产率得到methyl β-L-galactopyranosiduronic acid
  参考文献：
  名称：

  Glycosyltransferase catalyzed assemblage of sialyl-Lewisa-saccharopeptides

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(98)00229-8

文献信息

• 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.
• Glycosyl-transferase catalyzed assemblage of sialyl-lewis x -saccharopeptides
  作者：Gabi Baisch、Reinhold Öhrlein

  DOI：10.1016/s0968-0896(98)00107-2

  日期：1998.10

  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.