GlcNAc(b1-2)Man(a)-SPh | 239466-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: GlcNAc(b1-2)Man(a)-SPh
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 239466-00-3
• 化学式: C₂₀H₂₉NO₁₀S
• 分子量: 475.517
• InChiKey: XUSVHPIKLWDTRW-PRLMBHFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  204
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  GlcNAc(b1-2)Man(a)-SPh 、 4-硝基苯基-D-吡喃葡糖苷 以 水 、 二甲基亚砜 为溶剂， 以15%的产率得到Gal(b1-4)GlcNAc(b1-2)Man(a)-SPh
  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：

  O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-D-mannopyranose 在 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 GlcNAc(b1-2)Man(a)-SPh
  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.