α-Neu5Ac-(2->3)-β-D-Gal-(1->4)-D-Glc | 18409-13-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-Neu5Ac-(2->3)-β-D-Gal-(1->4)-D-Glc
• 英文别名: Neu5Acα2-3Galβ1-4Glc；3'-β-sialyllactose；3′-sialyllactose；3'-sialyllactose；NANA(α2-3)Gal(β1-4)Glc；NeuAc(b2-3)Gal(b1-4)Glc；(2R,4S,5R,6R)-5-acetamido-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 18409-13-7；64839-32-3；64839-33-4；102778-91-6；102778-92-7
• 化学式: C₂₃H₃₉NO₁₉
• 分子量: 633.558
• InChiKey: CILYIEBUXJIHCO-OVZNVPBESA-N

物化性质

• 沸点：
  1134.9±65.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -7.2
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  335
• 氢给体数：
  13
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  α-Neu5Ac-(2->3)-β-D-Gal-(1->4)-D-Glc 在 碳酸氢铵 作用下， 以 水 为溶剂， 反应 240.0h， 生成
  参考文献：
  名称：

  复杂的唾液寡糖向聚合物结合物的转化及其抗流感病毒的抑制能力

  摘要：

  为了研究不同的流感病毒株的特异性，我们已经准备undecasaccharide（Neu5Acα2-6Galβ1-4GlcNAcβ1-2Manα1）的聚丙烯型缀合物2 -3,6Manβ1-4GlcNAcβ1-4GlcNAc（YDS），和三糖6`-唾液酸Ñ -acetyllactosamine（ 6‵SLN），6‵唾液乳糖（6‵SL）和3‵唾液乳糖（3‵SL）。通过NH 4 HCO 3，氯乙酸酐和NH 3水溶液的顺序作用，将游离的寡糖转化为糖胺1- N-糖基衍生物。已知的衍生化方案已针对这些唾液寡糖进行了优化。所得氨基间隔的衍生物与聚（丙烯酸4-硝基苯酯）的偶联产生了两种类型的共轭物，即与聚丙烯酸和聚丙烯酰胺骨架。转化进行了定量，并且没有破坏寡糖。对于3‵SL，6‵SL，6‵SLN，缀合物中寡糖的含量分别为10、20和30％mol，对于YDS，低聚糖的含量为2、5和10％mol。测试了游离寡糖

  DOI：

  10.1080/07328300008544143
• 作为产物：
  描述：

  Lactose 、 CMP-Neu5Ac 在 α-2,3-selective β-D-galactoside sialyltransferase from Pasteurella dagmatis 、 bovine serum albumin 作用下， 以 aq. phosphate buffer 为溶剂， 以75%的产率得到α-Neu5Ac-(2->3)-β-D-Gal-(1->4)-D-Glc
  参考文献：
  名称：

  Complete switch from α-2,3- to α-2,6-regioselectivity in Pasteurella dagmatis β-d-galactoside sialyltransferase by active-site redesign

  摘要：

  在Pro7His和Met117Ala替换的情况下，得到了完全区域选择性和高效的α-2,6-唾液酸转移酶。

  DOI：

  10.1039/c4cc09772f

文献信息

• [EN] DIVERSIFICATION OF HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF<br/>[FR] DIVERSIFICATION D'OLIGOSACCHARIDES DU LAIT HUMAIN (HMO) OU DE LEURS PRÉCURSEURS
  申请人：GLYCOM AS

  公开号：WO2012156898A1

  公开（公告）日：2012-11-22

  A method of diversification of human milk oligosaccharides (HMOs) or precursors thereof, compounds obtainable by the method, and uses and compositions involving such compounds. The method comprises the steps of a) providing at least one compound or a mixture of the compounds selected from the group consisting of: optionally sialylated and/or fucosylated lactose derivatives of general formula 2 and salts thereof: (2) wherein R is a group removable by hydrogenolysis, R1 independently of each other is fucosyl or H, R4 independently of each other is sialyl or H, provided that the compound of general formula 2 is not R-glycoside of lactose, if provided alone; optionally sialylated and/or fucosylated lactose derivatives of general formula 4 and salts thereof: (4) wherein R1 independently of each other is fucosyl or H, R4 independently of each other is sialyl or H, provided that the compound of general formula 4 is not lactose, if provided alone; lacto-N-tetraose (LNT): (I) lacto-N-tetraose (LNT) derivatives of the following formula: (II) wherein R is a group removable by hydrogenolysis; lacto-N-neotetraose (LNnT): (III) lacto-N-neotetraose (LNnT) derivatives of the following formula: (IV) wherein R is a group removable by hydrogenolysis; b) adding at least one enzyme comprising a transglycosidase activity to the at least one compound or a mixture of compounds provided according to step a); and c) incubating the mixture obtained according to step b).

  一种多样化人类乳寡糖（HMOs）或其前体的方法，通过该方法获得的化合物以及涉及此类化合物的用途和组合物。该方法包括以下步骤：a）提供至少一种化合物或化合物混合物，所述化合物或混合物从以下组中选择：通式2的可选唾液酸化和/或岩藻糖化的乳糖衍生物及其盐：（2）其中R是可通过氢解去除的基团，R1独立地为岩藻糖基或H，R4独立地为唾液酸基或H，如果单独提供通式2的化合物，则不是乳糖的R-糖苷；通式4的可选唾液酸化和/或岩藻糖化的乳糖衍生物及其盐：（4）其中R1独立地为岩藻糖基或H，R4独立地为唾液酸基或H，如果单独提供通式4的化合物，则不是乳糖；乳糖N-四糖（LNT）：（I）以下式的乳糖N-四糖（LNT）衍生物：（II）其中R是可通过氢解去除的基团；乳糖N-新四糖（LNnT）：（III）以下式的乳糖N-新四糖（LNnT）衍生物：（IV）其中R是可通过氢解去除的基团；b）向根据步骤a）提供的至少一种化合物或化合物混合物中添加至少一种具有转移糖基酶活性的酶；以及c）孵育根据步骤b）获得的混合物。
• Liquid chromatography/tandem mass spectrometry with fluorous derivatization method for selective analysis of sialyl oligosaccharides
  作者：Yohei Sakaguchi、Tadashi Hayama、Hideyuki Yoshida、Miki Itoyama、Kenichiro Todoroki、Masatoshi Yamaguchi、Hitoshi Nohta

  DOI：10.1002/rcm.7042

  日期：2014.12.15

  A separation‐oriented derivatization method using a specific fluorous affinity between perfluoroalkyl‐containing compounds was applied to selective liquid chromatography/tandem mass spectrometric (LC/MS/MS) analysis of sialyl oligosaccharides. The perfluoroalkyl‐labeled sialyl oligosaccharides could be selectively retained on an LC column with the perfluoroalkyl‐modified stationary phase and effectively

  在含全氟烷基的化合物之间使用特定的氟亲和力的分离导向衍生化方法被用于唾液酸低聚糖的选择性液相色谱/串联质谱分析（LC / MS / MS）。全氟烷基标记的唾液酸寡糖可以通过全氟烷基改性的固定相选择性地保留在LC色谱柱上，并与非衍生化物种有效区分开。
• A new method for sequencing linear oligosaccharides on gels using charged, fluorescent conjugates
  作者：Kyung-Bok. Lee、Ali Al-Hakim、Duraikkannu Loganathan、Robert J. Linhardt

  DOI：10.1016/s0008-6215(00)90538-x

  日期：1991.8

  A new method is described for sequencing linear oligosaccharides on gels using charged, fluorescent conjugates. The reducing ends of various mono-, di-, tri-, and tetra-saccharides were conjugated with monopotassium 7-amino-1,3-naphthalenedisulfonate (a fluorescent and negatively charged compound) by reductive amination using sodium cyanoborohydride. The sugar conjugates were purified by preparative gradient polyacrylamide gel electrophoresis followed by a newly developed technique involving their semi-dry transfer to positively charged nylon membranes and elution with sodium chloride. The structures of a monosaccharide- and trisaccharide-conjugate were established by f.a.b.-m.s. and 2D n.m.r. Seven linear oligosaccharide-fluorescent conjugates were treated sequentially with exoglycosidases and with endoglycosidases. Analysis of the products by gel electrophoresis provided sequence information. These methods may be useful for sequencing oligosaccharides that are chemically or enzymically (endoglycosidase) released from glycoproteins, glycolipids, and proteoglycans.
• ITO, YUKISHIGE;OGAWA, TOMOYA, TETRAHEDRON, 46,(1990) N, C. 89-102
  作者：ITO, YUKISHIGE、OGAWA, TOMOYA

  DOI：——

  日期：——
• Complete switch from α-2,3- to α-2,6-regioselectivity in Pasteurella dagmatis β-<scp>d</scp>-galactoside sialyltransferase by active-site redesign
  作者：Katharina Schmölzer、Tibor Czabany、Christiane Luley-Goedl、Tea Pavkov-Keller、Doris Ribitsch、Helmut Schwab、Karl Gruber、Hansjörg Weber、Bernd Nidetzky

  DOI：10.1039/c4cc09772f

  日期：——

  Incorporation of Pro7His and Met117Ala substitutions resulted in a completely regioselective and highly efficient α-2,6-sialyltransferase.

  在Pro7His和Met117Ala替换的情况下，得到了完全区域选择性和高效的α-2,6-唾液酸转移酶。