D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-α-D-galactopyranose | 489-52-1

• 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-galactopyranose
• 英文别名: 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranose；galactosyl-β(1-3)-N-acetylgalactosamine；T-antigen；Galβ1->3GalNAcα；2-Acetamido-2-deoxy-3-O-(β-D-galaktopyranosyl)-α-D-galaktose；T-disaccharide；N-[(2S,3R,4R,5R,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: 489-52-1；3951-51-7；5143-15-7；20972-29-6；31718-87-3；32449-59-5；37090-84-9；75598-07-1；93601-70-8；109432-06-6；126060-76-2；148021-99-2
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: HMQPEDMEOBLSQB-IQKNWYLPSA-N

物化性质

• 熔点：
  159-160

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-galactopyranose 在 2,6-二甲基吡啶 、 Bacteroides thetaiotaomicron VPI5482 α-N-acetylglucosaminidase B1 作用下， 以 水 为溶剂， 反应 28.0h， 生成 4,6-dimethoxy-1,3,5-triazine-2-yl 2-acetamido-2-deoxy-3-O-(4-O-(2-acetamido-2-deoxy-α-glucopyranosyl)-β-galactopyranosyl)-α-galactopyranoside
  参考文献：
  名称：

  A dimethoxytriazine type glycosyl donor enables a facile chemo-enzymatic route toward α-linked N-acetylglucosaminyl-galactose disaccharide unit from gastric mucin

  摘要：

  现已开发出一种高效的化学酶法工艺，用于构建胃粘蛋白中的δ-连接双糖单元（GlcNAcδ±1-4Gal）。该工艺包括在水中一步制备新型三嗪型糖基供体，然后在δ-N-乙酰葡糖胺苷酶的催化下转糖基化为半乳糖衍生物。

  DOI：

  10.1039/c2cc30946g
• 作为产物：
  描述：

  在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-α-D-galactopyranose
  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

• Enzymatic and Chemoenzymatic Syntheses of Disialyl Glycans and Their Necrotizing Enterocolitis Preventing Effects
  作者：Hai Yu、Xuebin Yan、Chloe A Autran、Yanhong Li、Sabrina Etzold、Joanna Latasiewicz、Bianca M. Robertson、Jiaming Li、Lars Bode、Xi Chen

  DOI：10.1021/acs.joc.7b02167

  日期：2017.12.15

  novel disialyl glycans have been designed and synthesized by enzymatic or chemoenzymatic methods. Noticeably, two disialyl tetraoses have been produced by enzymatic sialylation of chemically synthesized thioethyl β-disaccharides followed by removal of the thioethyl aglycon. Dose-dependent and single-dose comparison studies showed varying NEC-preventing effects of the disialyl glycans in neonatal rats

  坏死性小肠结肠炎（NEC）是早产儿中最常见和最具破坏性的肠道疾病之一。满足这种特殊和高度脆弱人群临床需求的疗法极为有限。特定的人乳低聚糖（HMO），二唾液酸内酯-N-四糖（DSLNT）被证明有助于母乳喂养，因为它可以预防新生大鼠模型中的NEC，并且在一项人类临床研究中与较低的NEC风险相关。本文中，描述了先前显示出具有NEC预防作用的两个DSLNT类似物的克级合成。另外，已经通过酶促或化学酶促方法设计和合成了四种新颖的二唾液酸聚糖。明显地，通过化学合成的硫乙基β-二糖的酶促唾液酸化，然后除去硫乙基糖苷配基，已经产生了两种二唾液酸四糖。剂量依赖性和单剂量比较研究表明，新生大鼠中二唾液酸聚糖的NEC预防作用各不相同。
• Method for measuring glycosyltransferase activity
  申请人：Mount Sinai Hospital Corporation

  公开号：US05501957A1

  公开（公告）日：1996-03-26

  A method of assaying for glycosyltransferase activity in a sample. In a first step, a sample is reacted with a first sugar donor and an acceptor substrate to produce a transferase product. The first sugar donor and acceptor substrate are selected such that the sugar from the first sugar donor is capable of being transferred to the acceptor substrate in the presence of the glycosyltransferase to be assayed. In a second step, the transferase product is reacted with a second sugar donor having a sugar which is labelled with a labelling agent and an enzyme which is capable of transferring the sugar from the second sugar donor to the transferase product to produce a labelled transferase product and which has a higher affinity for the glycosyltransferase product compared to the affinity of the glycosyltransferase for the acceptor substrate. The labelling agent activity of the labelled transferase product or unreacted second sugar donor is assayed to determine transferase activity in the sample. A kit for assaying for glycosyltransferase activity in a sample is also described.

  一种在样品中检测糖基转移酶活性的方法。首先，将样品与第一种糖供体和受体底物反应，产生转移酶产物。第一种糖供体和受体底物被选择为第一种糖供体的糖在糖基转移酶存在下能够转移到受体底物。其次，将转移酶产物与第二种糖供体反应，该糖含有标记试剂，酶能够将第二种糖供体的糖转移到转移酶产物上，产生带标记的转移酶产物。该酶对糖基转移酶产物的亲和力高于对受体底物的亲和力。测定带标记的转移酶产物或未反应的第二种糖供体的标记试剂活性，以确定样品中的转移酶活性。还描述了用于检测样品中糖基转移酶活性的试剂盒。
• 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.
• US4767845A
  申请人：——

  公开号：US4767845A

  公开（公告）日：1988-08-30
• US4794176A
  申请人：——

  公开号：US4794176A

  公开（公告）日：1988-12-27