benzyl-O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl-O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: Neu5Ac2-3Gal1-4-GlaNAc-OBn; Sial(alpha2,3)Gal(beta1,4)GlcNAc-oBn；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-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: C₃₂H₄₈N₂O₁₉
• 分子量: 764.735
• InChiKey: PGWZIARJSVVTOB-GHVOKIGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  333
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  [(2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-4-acetyloxy-2-(phosphonooxymethyl)oxolan-3-yl] acetate 在 DL-dithiothreitol 、 magnesium chloride sodium hydroxide 、 HEPES buffer 、 Neisseria α(2,3)-sialyltransferase 、 sodium methylate 、 alkaline phosphatase 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 benzyl-O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  用于碳水化合物合成的微生物糖基转移酶：来自奈瑟氏淋球菌的 α-2,3-唾液酸转移酶

  摘要：

  来自淋病奈瑟菌的 α-2,3-唾液酸转移酶在大肠杆菌中过度生产，以利用其底物特异性和合成效用。本研究合成了几种潜在的受体底物，包括单糖和寡糖、糖脂、糖肽及其硫酸盐衍生物。还制备了一些在 C-5 位进行修饰的 CMP-唾液酸衍生物作为供体底物进行评估。发现与其他唾液酸转移酶相比，该酶表现出更广泛的受体底物特异性，尽管供体特异性非常有限。已证明该酶在代表性唾液酸糖缀合物的制备性合成中的应用。在这项工作和其他人的工作的基础上，

  DOI：

  10.1021/ja011382r

文献信息

• Porcine liver (2 → 3)-α-sialyltransferase: substrate specificity studies and application of the immobilized enzyme to the synthesis of various sialylated oligosaccharide sequences
  作者：André Lubineau、Karine Basset-Carpentier、Claudine Augé

  DOI：10.1016/s0008-6215(97)00043-8

  日期：1997.5

  In search of substrate analogues for the porcine liver beta-D-Galp-(1 --> 3)-D-Galp-NAc: CMP-Neu5Ac-(2 --> 3')-alpha-sialyltransferase, three disaccharides beta-D-Galp-(1 --> 3)-beta-D-Galp-O-CH3 (5), beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-CH3 (7) and beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-Bn (11) were synthesized and tested with the enzyme. Disaccharide 7 turned out to be a very good substrate allowing a rapid access to the trisaccharide alpha-Neu5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-P-D-(2-OAc)-Galp-O-CH3 (13) on a preparative scale using the crude enzyme immobilized on cationic exchanger. Trisaccharide 13 was further exploited, first as a sialyl donor in Trypanosoma cruzi trans-sialidase catalyzed reaction and second through acetolysis reaction as a source for the synthon alpha-Neu5Ac-(2 --> 3)-D-Gal (16). (C) 1997 Elsevier Science Ltd.
• Jain, Rakesh K.; Vig, Rakesh; Locke, Robert D., Journal of the Chemical Society Chemical Communications, 1996, # 1, p. 65 - 68
  作者：Jain, Rakesh K.、Vig, Rakesh、Locke, Robert D.、Mohammad, Asif、Matta, Khushi L.

  DOI：——

  日期：——
• Microbial Glycosyltransferases for Carbohydrate Synthesis:  α-2,3-Sialyltransferase from <i>Neisseria </i><i>g</i><i>onorrheae</i>
  作者：Masayuki Izumi、Gwo-Jenn Shen、Shirley Wacowich-Sgarbi、Takuji Nakatani、Oliver Plettenburg、Chi-Huey Wong

  DOI：10.1021/ja011382r

  日期：2001.11.1

  exploitation of its substrate specificity and synthetic utility. Several potential acceptor substrates were synthesized in this study, including mono- and oligosaccharides, glycolipids, and glycopeptides and their sulfate derivatives. Some CMP-sialic acid derivatives with modification at the C-5 position were also prepared for evaluation as donor substrates. It was found that the enzyme exhibits a broader

  来自淋病奈瑟菌的 α-2,3-唾液酸转移酶在大肠杆菌中过度生产，以利用其底物特异性和合成效用。本研究合成了几种潜在的受体底物，包括单糖和寡糖、糖脂、糖肽及其硫酸盐衍生物。还制备了一些在 C-5 位进行修饰的 CMP-唾液酸衍生物作为供体底物进行评估。发现与其他唾液酸转移酶相比，该酶表现出更广泛的受体底物特异性，尽管供体特异性非常有限。已证明该酶在代表性唾液酸糖缀合物的制备性合成中的应用。在这项工作和其他人的工作的基础上，