methyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 100605-31-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: Neu5Acα(2,3)Lacβ1Me；NeuAc(a2-3)Gal(b1-4)b-Glc1Me；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-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: 100605-31-0
• 化学式: C₂₄H₄₁NO₁₉
• 分子量: 647.585
• InChiKey: LSQCOHATXULXKJ-YQJFHFFOSA-N

物化性质

• 沸点：
  1088.0±65.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.7
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  324
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 MS 4 Angstroem 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 methyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Preliminary 1H NMR investigation of sialic acid transfer by the trans-sialidase from Trypanosoma cruzi

  摘要：

  H-1 NMR spectroscopy has been used to investigate the transfer of sialic acid from sialic acid donor molecules to acceptor molecules using the trans-sialidase from Typanosoma cruzi. It is clearly demonstrated that NMR spectroscopy is an efficient and powerful means of monitoring the trans-sialidase promoted transfer of sialic acid from donor to acceptor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00572-2

文献信息

• A Multifunctional <i>Pasteurella multocida</i> Sialyltransferase:  A Powerful Tool for the Synthesis of Sialoside Libraries
  作者：Hai Yu、Harshal Chokhawala、Rebekah Karpel、Hui Yu、Bingyuan Wu、Jianbo Zhang、Yingxin Zhang、Qiang Jia、Xi Chen

  DOI：10.1021/ja0561690

  日期：2005.12.1

  A multifunctional sialyltransferase has been cloned from Pasteurella multocida strain P-1059 and expressed in E. coli as a truncated C-terminal His6-tagged recombinant protein (tPm0188Ph). Biochemical studies indicate that the obtained protein is (1) an alpha2,3-sialyltransferase (main function), (2) an alpha2,6-sialyltransferase, (3) an alpha2,3-sialidase, and (4) an alpha2,3-trans-sialidase. The recombinant tPm0188Ph is a powerful tool in the synthesis of structurally diverse sialoside libraries due to its relaxed substrate specificity, high solubility, high expression level, and multifunctionality.
• Thiem, Joachim; Sauerbrei, Bernd, Angewandte Chemie, 1991, vol. 103, # 11, p. 1521 - 1523
  作者：Thiem, Joachim、Sauerbrei, Bernd

  DOI：——

  日期：——
• Preliminary 1H NMR investigation of sialic acid transfer by the trans-sialidase from Trypanosoma cruzi
  作者：Jennifer C Wilson、Milton J Kiefel、Samia Albouz-Abo、Mark von Itzstein

  DOI：10.1016/s0960-894x(00)00572-2

  日期：2000.12

  H-1 NMR spectroscopy has been used to investigate the transfer of sialic acid from sialic acid donor molecules to acceptor molecules using the trans-sialidase from Typanosoma cruzi. It is clearly demonstrated that NMR spectroscopy is an efficient and powerful means of monitoring the trans-sialidase promoted transfer of sialic acid from donor to acceptor. (C) 2000 Elsevier Science Ltd. All rights reserved.