azido 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

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: azido 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: NeuAc(a2-3)Gal(b1-4)Glc(b)-N3；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-azido-4,5-dihydroxy-2-(hydroxymethyl)oxan-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
• 化学式: C₂₃H₃₈N₄O₁₈
• 分子量: 658.571
• InChiKey: FRNVDYWGQXBPFR-UITFWXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  329
• 氢给体数：
  12
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  N-acetyl-D-mannosamine 、 1-叠氮-1-脱氧-Β-D-吡喃乳糖苷 、 sodium pyruvate 在 E_.coli K₁₂ sialic acid aldolase 、 N_.meningitidis CMP-Sia synthetase tPm₀₁₈₈Ph 、 胞苷-5’-三磷酸 、 magnesium chloride 作用下， 以 various solvents 为溶剂， 反应 2.0h， 以92%的产率得到azido 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：

  A Multifunctional Pasteurella multocida Sialyltransferase:  A Powerful Tool for the Synthesis of Sialoside Libraries

  摘要：

  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.

  DOI：

  10.1021/ja0561690

文献信息

• Enzymatic Sialylation of Synthetic Multivalent Scaffolds: From 3′‐Sialyllactose Glycomacromolecules to Novel Neoglycosides
  作者：Patrick B. Konietzny、Hannelore Peters、Marc L. Hofer、Ulla I. M. Gerling‐Driessen、Robert P. de Vries、Thomas Peters、Laura Hartmann

  DOI：10.1002/mabi.202200358

  日期：2022.12

  and sialyltransferase from Pasteurella multocida (PmST1) are combined in a one-pot reaction giving access to sequence-defined sialylated macromolecules. Surprisingly, when employing Tris(hydroxymethyl)aminomethane (Tris) as a buffer, formation of significant amounts of α-linked Tris-sialoside is observed as a side reaction. Further exploring and exploiting this unusual sialylation reaction, different

  唾液酸聚糖在许多生物识别过程中起着关键作用，各种类型的唾液酸化缀合物已成功应用，例如，作为抗病毒药或用于抗肿瘤治疗。这种缀合物的高亲和力结合的一个关键特征是唾液酸聚糖的多价呈递，这通常具有合成挑战。在这里，描述了固相聚合物合成和酶促唾液酸化产生 3'-唾液酸乳糖呈递的精密糖大分子的组合。来自脑膜炎奈瑟菌(NmCSS)的 CMP-Neu5Ac 合成酶和来自多杀性巴氏杆菌的唾液酸转移酶(PmST1) 在一锅反应中组合，可以访问序列定义的唾液酸化大分子。令人惊讶的是，当使用三（羟甲基）氨基甲烷 (Tris) 作为缓冲液时，作为副反应观察到大量α-连接的 Tris-唾液酸苷的形成。进一步探索和利用这种不寻常的唾液酸化反应，合成了不同的新糖苷结构，表明 PmST1 可用于衍生天然碳水化合物和合成羟基化支架上的唾液酸化。
• 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.