phenyl β-D-galactopyranosyl)-(1-> 4)-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-> 3)-β-D-galactopyranosyl-(-> 4)-1-thio-β-D-glucopyranoside | 301663-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl β-D-galactopyranosyl)-(1-> 4)-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-> 3)-β-D-galactopyranosyl-(-> 4)-1-thio-β-D-glucopyranoside
• 英文别名: Gal(b1-4)GlcNAc(b1-3)Gal(b1-4)Glc(b)-SPh；N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 301663-21-8
• 化学式: C₃₂H₄₉NO₂₀S
• 分子量: 799.802
• InChiKey: NAZKWQZKXVCMMA-XJISQGHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  362
• 氢给体数：
  13
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  N-acetylneuraminic acid sodium salt 、 phenyl β-D-galactopyranosyl)-(1-> 4)-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-> 3)-β-D-galactopyranosyl-(-> 4)-1-thio-β-D-glucopyranoside 生成 phenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2-> 3)-β-D-galactopyranosyl-(1-> 4)-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-> 3)-β-D-galactopyranosyl-(1-> 4)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Polymer-supported and chemoenzymatic synthesis of the Neisseria meningitidis pentasaccharide: a methodological comparison

  摘要：

  Neisseria meningitidis trisaccharide [GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], tetrasaccharide [Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], and a pentasaccharide [Neu5Ac alpha(2 --> 3)Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-SPh] were prepared via conventional chemical synthesis, polymer-supported synthesis, and chemoenzymatic methods, starting from D-lactose. The polymer polyethyleneglycol monomethylether (MPEG) and the linker dioxyxylene (DOX) were used with a lactose-bound acceptor to improve the purification process. Several enzymes (LgtA, GalE-LgtB fusion, and CMP-Neu5Ac synthetase/sialyltransferase fusion) were used for syntheses of these oligosaccharides. Excellent stereo- and regioselectivities as well as high yield (> 90% from Gal beta(1 --> 4)Glc-SPh) of the pentasaccharide were obtained. Both of the convenient processes are suitable for efficient preparation of target oligosaccharides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00086-0
• 作为产物：
  描述：

  β-phenylsulfanyl lactoside 生成 phenyl β-D-galactopyranosyl)-(1-> 4)-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-> 3)-β-D-galactopyranosyl-(-> 4)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Polymer-supported and chemoenzymatic synthesis of the Neisseria meningitidis pentasaccharide: a methodological comparison

  摘要：

  Neisseria meningitidis trisaccharide [GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], tetrasaccharide [Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], and a pentasaccharide [Neu5Ac alpha(2 --> 3)Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-SPh] were prepared via conventional chemical synthesis, polymer-supported synthesis, and chemoenzymatic methods, starting from D-lactose. The polymer polyethyleneglycol monomethylether (MPEG) and the linker dioxyxylene (DOX) were used with a lactose-bound acceptor to improve the purification process. Several enzymes (LgtA, GalE-LgtB fusion, and CMP-Neu5Ac synthetase/sialyltransferase fusion) were used for syntheses of these oligosaccharides. Excellent stereo- and regioselectivities as well as high yield (> 90% from Gal beta(1 --> 4)Glc-SPh) of the pentasaccharide were obtained. Both of the convenient processes are suitable for efficient preparation of target oligosaccharides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00086-0

文献信息

• Polymer-supported and chemoenzymatic synthesis of the Neisseria meningitidis pentasaccharide: a methodological comparison
  作者：Fengyang Yan、Warren W. Wakarchuk、Michel Gilbert、James C. Richards、Dennis M. Whitfield

  DOI：10.1016/s0008-6215(00)00086-0

  日期：2000.8

  Neisseria meningitidis trisaccharide [GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], tetrasaccharide [Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-R], and a pentasaccharide [Neu5Ac alpha(2 --> 3)Gal beta(1 --> 4)GlcNAc beta(1 --> 3)Gal beta(1 --> 4)Glc-SPh] were prepared via conventional chemical synthesis, polymer-supported synthesis, and chemoenzymatic methods, starting from D-lactose. The polymer polyethyleneglycol monomethylether (MPEG) and the linker dioxyxylene (DOX) were used with a lactose-bound acceptor to improve the purification process. Several enzymes (LgtA, GalE-LgtB fusion, and CMP-Neu5Ac synthetase/sialyltransferase fusion) were used for syntheses of these oligosaccharides. Excellent stereo- and regioselectivities as well as high yield (> 90% from Gal beta(1 --> 4)Glc-SPh) of the pentasaccharide were obtained. Both of the convenient processes are suitable for efficient preparation of target oligosaccharides. (C) 2000 Elsevier Science Ltd. All rights reserved.