(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3S,4S,5S,6R)-2-[(2S)-2-carboxy-2-(phenylmethoxycarbonylamino)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid | 239466-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3S,4S,5S,6R)-2-[(2S)-2-carboxy-2-(phenylmethoxycarbonylamino)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 239466-06-9
• 化学式: C₄₂H₆₃N₃O₂₈
• 分子量: 1057.97
• InChiKey: PTZXRYGCNVRXHN-YMVKRGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.4
• 重原子数：
  73
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  488
• 氢给体数：
  17
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3S,4S,5S,6R)-2-[(2S)-2-carboxy-2-(phenylmethoxycarbonylamino)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid 在 钯 氢气 作用下， 以 水 为溶剂， 生成 Neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-Ser
  参考文献：
  名称：

  The first synthesis of neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-ser — a newly discovered component of α-dystroglycan

  摘要：

  Glycopeptide (1), Neu5Aca2-3Gal beta 1-4GlcNAc beta 1-2Man alpha 1-Ser, was synthesized using a chemoenzymatic strategy. Gal beta 1-4GlcNA beta 1-2Man trisaccharide was prepared using glycosidase assisted oligosaccharide synthesis. After coupling of this trisaccharide with a serine derivative by chemical glycosylation, sialic add was introduced using sialyltransferase to produce a tetrasaccharide serine derivative. Removal of protecting group afforded glycopeptide (1). Use of a chemoenzymatic strategy allowed for the elimination of numerous synthetic steps and efficient preparation of the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00930-2
• 作为产物：
  描述：

  在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 cacodylate buffer 、 水 、 sodium methylate 、 溶剂黄146 、 bovine serum albumin 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3S,4S,5S,6R)-2-[(2S)-2-carboxy-2-(phenylmethoxycarbonylamino)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  The first synthesis of neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-ser — a newly discovered component of α-dystroglycan

  摘要：

  Glycopeptide (1), Neu5Aca2-3Gal beta 1-4GlcNAc beta 1-2Man alpha 1-Ser, was synthesized using a chemoenzymatic strategy. Gal beta 1-4GlcNA beta 1-2Man trisaccharide was prepared using glycosidase assisted oligosaccharide synthesis. After coupling of this trisaccharide with a serine derivative by chemical glycosylation, sialic add was introduced using sialyltransferase to produce a tetrasaccharide serine derivative. Removal of protecting group afforded glycopeptide (1). Use of a chemoenzymatic strategy allowed for the elimination of numerous synthetic steps and efficient preparation of the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00930-2

文献信息

• The first synthesis of neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-ser — a newly discovered component of α-dystroglycan
  作者：Ichiro Matsuo、Megumi Isomura、Katsumi Ajisaka

  DOI：10.1016/s0040-4039(99)00930-2

  日期：1999.7

  Glycopeptide (1), Neu5Aca2-3Gal beta 1-4GlcNAc beta 1-2Man alpha 1-Ser, was synthesized using a chemoenzymatic strategy. Gal beta 1-4GlcNA beta 1-2Man trisaccharide was prepared using glycosidase assisted oligosaccharide synthesis. After coupling of this trisaccharide with a serine derivative by chemical glycosylation, sialic add was introduced using sialyltransferase to produce a tetrasaccharide serine derivative. Removal of protecting group afforded glycopeptide (1). Use of a chemoenzymatic strategy allowed for the elimination of numerous synthetic steps and efficient preparation of the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.