D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-α-D-glucopyranose | 37090-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-α-D-glucopyranose
• 英文别名: β-D-galactopyranosyl-(1–3)-2-acetamido-2-deoxy-D-glucopyranose；lacto-N-biose；2-Acetamido-2-deoxy-3-O-<β-D-galactopyranosyl>-β-D-glucose；2-Acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-β-D-glucose；2-Acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-D-glucopyranose；N-[(2S,3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 37090-84-9
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: HMQPEDMEOBLSQB-RCBHQUQDSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  198
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-α-D-glucopyranose 在 2-chloro-1,3-dimethyl-1H-benzimidazole-3-ium chloride 、 sodium phosphate 作用下， 以 水 为溶剂， 反应 1.5h， 以93%的产率得到(2R,3R,4S,5R,6R)-2-[[(3aR,5R,6S,7R,7aR)-6-hydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  实用的一步法从未保护的糖中合成1,2-恶唑啉衍生物及其在化学酶法β-N-乙酰氨基葡萄糖二唾液寡糖氨基化中的应用

  摘要：

  通过使用2-氯-1,3--3-二甲基-1H-苯并咪唑-3-氯化铵，开发了一种从相应的N-乙酰-2-氨基糖合成糖恶唑啉（=二氢恶唑）的简便实用方法。CDMBI）作为脱水缩合剂。未保护的N-乙酰-2-氨基糖的2-乙酰氨基基团与端基OH基团之间的分子内脱水反应在H 2 O中平稳进行，导致形成1,2-恶唑啉（= 4,5-二氢恶唑）部分，收率很好。由于反应在H 2中进行在不使用任何保护基的情况下，所得的恶唑啉可用作有效的糖基供体，用于随后的酶促糖基化。我们已经成功地证明了由突变型内切N-乙酰氨基葡糖苷酶催化的二低聚寡糖部分到对硝基苯基N-乙酰氨基葡糖苷的高效化学酶转糖基化反应，而没有分离出二聚寡糖恶唑啉作为合成中间体。

  DOI：

  10.1002/hlca.201200414
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R)-6-acetoxy-2-acetoxymethyl-5-acetylamino-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-α-D-glucopyranose 、 (3-aminopropyl)-β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units

  摘要：

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.

  DOI：

  10.1021/jo00068a030

文献信息

• The characterisation of a galactokinase from Streptomyces coelicolor
  作者：Tessa Keenan、Rhys Mills、Emily Pocock、Darshita Budhadev、Fabio Parmeggiani、Sabine Flitsch、Martin Fascione

  DOI：10.1016/j.carres.2018.12.005

  日期：2019.1

  Promiscuous galactokinases (GalKs), which catalyse the ATP dependent phosphorylation of galactose in nature, have been widely exploited in biotechnology for the rapid synthesis of diverse sugar-1-phosphates. This work focuses on the characterisation of a bacterial GalK from Streptomyces coelicolor (ScGalK), which was overproduced in Escherichia coli and shown to phosphorylate galactose. ScGalK displayed

  混杂半乳糖激酶（GalKs）催化自然界中半乳糖的ATP依赖性磷酸化，已在生物技术中得到广泛利用，以快速合成各种糖-1-磷酸。这项工作的重点是表征一种来自Coelicolor链霉菌（ScGalK）的细菌GalK的特性，该细菌在大肠杆菌中过量生产，并且可以磷酸化半乳糖。ScGalK具有广泛的底物耐受性，对Gal，GalN，Gal3D，GalNAc，Man和L-Ara具有活性。最有趣的是，ScGalK在很宽的pH和温度范围内显示出高活性，表明该酶可能高度适合多酶系统。
• Preparation for the application of agents in mini-droplets
  申请人：Cevc Gregor

  公开号：US20070042030A1

  公开（公告）日：2007-02-22

  The invention relates to a preparation for the application of agents in the form of minuscule droplets of fluid, in particular provided with membrane-like structures consisting of one or several layers of amphiphilic molecules, or an amphiphilic carrier substance, in particular for transporting the agent into and through natural barriers such as skin and similar materials. The preparation contains a concentration of edge active substances which amounts to up to 99 mol-% of the agent concentration which is required for the induction of droplet solubilization. Such preparations are suitable, for example, for the non-invasive applications of antidiabetics, in particular of insulin. The invention, moreover, relates to the methods for the preparation of such formulations.
• COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS
  申请人：Washington University

  公开号：US20210171563A1

  公开（公告）日：2021-06-10

  The present invention is directed to various compounds, compositions, and methods for treating bacterial infections such as urinary tract infections.
• US6165500A
  申请人：——

  公开号：US6165500A

  公开（公告）日：2000-12-26
• A Practical One-Step Synthesis of 1,2-Oxazoline Derivatives from Unprotected Sugars and Its Application to Chemoenzymatic<i>β</i>-<i>N</i>-Acetylglucosaminidation of Disialo-oligosaccharide
  作者：Masato Noguchi、Tsukasa Fujieda、Wei Chun Huang、Masaki Ishihara、Atsushi Kobayashi、Shin-ichiro Shoda

  DOI：10.1002/hlca.201200414

  日期：2012.10

  facile and practical method for synthesis of sugar oxazolines (=dihydrooxazoles) from the corresponding N‐acetyl‐2‐amino sugars has been developed by using 2‐chloro‐1,3‐dimethyl‐1H‐benzimidazol‐3‐ium chloride (CDMBI) as a dehydrative condensing agent. The intramolecular dehydrative reaction between the 2‐acetamido group and the anomeric OH group of unprotected N‐acetyl‐2‐amino sugars took place smoothly

  通过使用2-氯-1,3--3-二甲基-1H-苯并咪唑-3-氯化铵，开发了一种从相应的N-乙酰-2-氨基糖合成糖恶唑啉（=二氢恶唑）的简便实用方法。CDMBI）作为脱水缩合剂。未保护的N-乙酰-2-氨基糖的2-乙酰氨基基团与端基OH基团之间的分子内脱水反应在H 2 O中平稳进行，导致形成1,2-恶唑啉（= 4,5-二氢恶唑）部分，收率很好。由于反应在H 2中进行在不使用任何保护基的情况下，所得的恶唑啉可用作有效的糖基供体，用于随后的酶促糖基化。我们已经成功地证明了由突变型内切N-乙酰氨基葡糖苷酶催化的二低聚寡糖部分到对硝基苯基N-乙酰氨基葡糖苷的高效化学酶转糖基化反应，而没有分离出二聚寡糖恶唑啉作为合成中间体。