(2S)-3-[(2S,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoic acid | 239466-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-3-[(2S,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 239466-05-8
• 化学式: C₃₁H₄₆N₂O₂₀
• 分子量: 766.708
• InChiKey: UNWMVYQUJWQEIT-HBKQZYIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  342
• 氢给体数：
  12
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  (2S)-3-[(2S,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoic acid 在 钯 cacodylate buffer 、 氢气 、 bovine serum albumin 作用下， 以 水 为溶剂， 反应 48.0h， 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：

  Gal2Ac3Ac4Ac6Ac(b1-4)GlcNAc3Ac6Ac(b1-2)Man3Ac4Ac6Ac(a)-SPh 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 水 、 sodium methylate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2S)-3-[(2S,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoic 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.