methyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranoside | 136378-93-3

• 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-galactopyranoside
• 英文别名: Neu5Acα(2,3)Galβ1Me；methyl (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranoside；Neu5Ac-2-O-α-(2->3)-GalβMe；methyl [(3,5-dideoxy-5-acetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onic acid](2→3)-β-D-galactopyranoside；NeuAc(a2-3)b-Gal1Me；(2S,4S,5R,6R)-5-acetamido-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 136378-93-3
• 化学式: C₁₈H₃₁NO₁₄
• 分子量: 485.442
• InChiKey: KMPGBWYXWJYCKQ-BOROWPCNSA-N

物化性质

• 沸点：
  924.6±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranoside 在 Vibrio cholerae sialidase 作用下， 以 重水 为溶剂， 反应 2.0h， 生成 N-acetyl neuraminic acid 、 甲基-Β-D-吡喃半乳糖苷
  参考文献：
  名称：

  Investigation of the Stability of Thiosialosides toward Hydrolysis by Sialidases Using NMR Spectroscopy

  摘要：

  H-1 NMR spectroscopy has been used to investigate whether the alpha(2-->6)-linked thiosialoside 3 and the alpha(2-->3)-linked thiosialoside 9 are hydrolyzed in the presence of Vibrio cholerae sialidase, Similarly, the hydrolysis of the O-ketosides Neu5Ac-2-O-alpha-(2-->3)-Gal beta Me (4) and the alpha-(2-->6)-sialyllactoside 7, representing natural alpha(2-->3)- and alpha(2-->6)-linked sialosides, respectively, was investigated. The results of the H-1 NMR experiments clearly demonstrate that the thiosialosides are not hydrolyzed by Vibrio cholerae sialidase, As expected, the O-sialosides are hydrolyzed to give N-acetyl-alpha-D-neuraminic acid as the first product of substrate cleavage.

  DOI：

  10.1021/ol990652w
• 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 、 4 A molecular sieve 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 methyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranoside
  参考文献：
  名称：

  Investigation of the Stability of Thiosialosides toward Hydrolysis by Sialidases Using NMR Spectroscopy

  摘要：

  H-1 NMR spectroscopy has been used to investigate whether the alpha(2-->6)-linked thiosialoside 3 and the alpha(2-->3)-linked thiosialoside 9 are hydrolyzed in the presence of Vibrio cholerae sialidase, Similarly, the hydrolysis of the O-ketosides Neu5Ac-2-O-alpha-(2-->3)-Gal beta Me (4) and the alpha-(2-->6)-sialyllactoside 7, representing natural alpha(2-->3)- and alpha(2-->6)-linked sialosides, respectively, was investigated. The results of the H-1 NMR experiments clearly demonstrate that the thiosialosides are not hydrolyzed by Vibrio cholerae sialidase, As expected, the O-sialosides are hydrolyzed to give N-acetyl-alpha-D-neuraminic acid as the first product of substrate cleavage.

  DOI：

  10.1021/ol990652w

文献信息

• Chemoenzymatic Synthesis of Sialyl Oligosaccharides with Sialidases Employing Transglycosylation Methodology
  作者：Dirk Schmidt、Bernd Sauerbrei、Joachim Thiem

  DOI：10.1021/jo000871r

  日期：2000.12.1

  disease virus show a distinct preference for alpha(2-3) directed sialylations. Using combined chemical and enzymatic methodologies structures such as T-(Thomsen-Friedenreich) antigen [beta-D-Gal-(1-3)-alpha-D-GalNAc-OThr], Tn-(Thomsen nouveau) antigen (alpha-D-GalNAc-OThr) and beta-D-Gal-(1-4)-alpha-D-2-deoxy-Gal-OMe were sialylated in alpha(2-3)- and alpha(2-6)-positions regioselectively or in high

  利用霍乱弧菌，产气荚膜梭菌，鼠伤寒沙门氏菌和新城疫病毒的唾液酸酶的转糖活性，合成了一系列唾液寡糖。根据它们的水解活性，霍乱弧菌和产气荚膜梭菌的唾液酸酶优先催化唾液酸α（2-6）-键的形成，而伤寒沙门氏菌和新城疫病毒的唾液酸酶对α（2-3）表现出明显的偏爱。 ）定向唾液酸化。使用诸如T-（Thomsen-Friedenreich）抗原[β-D-Gal-（1-3）-α-D-GalNAc-OThr]的化学和酶学组合方法，在α（2-3）-中将Tn-（Thomsen nouveau）抗原（α-D-GalNAc-OThr）和β-D-Gal-（1-4）-α-D-2-脱氧-Gal-OMe唾液酸化。和α（2-6）-位置选择性或高区域异构体过量，并通过简单的分离程序纯化。取决于酶源和受体结构，转唾液酸化的产率在10％至30％之间变化。
• Synthesis of sialyloligosaccharides using the trans-sialidase from Trypanosoma cruzi: novel branched and di-sialylated products from digalactoside acceptors
  作者：Suddham Singh、Michaela Scigelova、Marianne Lilja Hallberg、Oliver W. Howarth、David H. G. Crout、Sergio Schenkman

  DOI：10.1039/b002302g

  日期：——

  The trans-sialidase from Trypanosoma cruzi efficiently catalyses transfer of α-sialyl residues from p-nitrophenyl sialic acid (p-nitrophenyl N-acetylneuraminic acid) to acceptors containing β-galactose units.

  来自克氏锥虫的转唾液酸酶 有效催化 α-唾液酸残基的转移 对硝基苯基唾液酸（对硝基苯基 N-乙酰神经氨酸）到含有β-半乳糖的受体 单位。
• Stereoselective Synthesis of 5-<i>epi</i>-α-Sialosides Related to the Pseudaminic Acid Glycosides. Reassessment of the Stereoselectivity of the 5-Azido-5-deacetamidosialyl Thioglycosides and Use of Triflate as Nucleophile in the Zbiral Deamination of Sialic Acids
  作者：Bibek Dhakal、Szymon Buda、David Crich

  DOI：10.1021/acs.joc.6b02221

  日期：2016.11.18

  With a view to the eventual synthesis of glycosyl donors for the stereocontrolled synthesis of pseudaminic acid glycosides, the stereocontrolled synthesis of a d-glycero-d-gulo sialic acid adamantanylthioglycoside carrying an axial azide at the 5-position is described. The synthesis employs levulinic acid as nucleophile in the oxidative deamination of an N-acetylneuraminic acid thioglycoside leading

  为了最终合成用于立体控制合成假氨基酸糖苷的糖基供体，描述了在5-位携带轴向叠氮化物的d-甘油-d-古洛糖唾液酸金刚烷基硫糖苷的立体控制合成。该合成采用乙酰丙酸作为亲核试剂，对N-乙酰神经氨酸硫代糖苷进行氧化脱氨，从而形成选择性保护为 5- O的 3-脱氧-d-甘油-d-半乳糖-2-nonulosonic 酸 (KDN) 衍生物-乙酰丙酸。用三氟甲磺酸酯替代乙酰丙酸酯能够引入轴向叠氮化物，从而形成糖基供体。当直接获得 5- O-三氟甲磺酸基 KDN 衍生物时，更短的合成在氧化脱氨步骤中使用三氟甲磺酸盐作为亲核试剂。在-78℃下用5-叠氮基-d-甘油-d- gulo配置的唾液酸金刚烷基硫代糖苷进行的糖基化反应对于赤道糖苷的形成具有选择性，这表明赤道伪胺酸糖苷的合成将有可能作为合适的供体变得可用。还发现在 5 位带有赤道叠氮化物的类似N-乙酰神经氨酸金刚烷硫糖苷在相同条件下对赤道糖苷形成具有选择
• 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.
• 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.