甲基 2-乙酰氨基-2-脱氧-3-O-(beta-D-吡喃半乳糖基)-alpha-D-吡喃半乳糖苷 | 75669-79-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基 2-乙酰氨基-2-脱氧-3-O-(beta-D-吡喃半乳糖基)-alpha-D-吡喃半乳糖苷
• 中文别名: 甲基2-乙酰氨基-2-脱氧-3-O-(beta-D-吡喃半乳糖基)-alpha-D-吡喃半乳糖苷；3-吲哚基2-乙酰氨基-2-脱氧-bD-吡喃葡萄糖苷
• 英文名称: methyl O-(β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: methyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside；β-D-Galp-(1->3)-α-D-GalpNAc-O-Me；β-D-Galp-(1->3)-α-GalpNAc-OMe；T-antigen-α；β-Galp-(1->3)-α-GalpNAcOMe；N-[(2S,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-methoxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 75669-79-3
• 化学式: C₁₅H₂₇NO₁₁
• 分子量: 397.379
• InChiKey: JPIHIQIYWZWIPU-ATCGGQGBSA-N

物化性质

• 熔点：
  270-272°C dec.
• 沸点：
  743.3±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  O-甲基-N-乙酰基-2-脱氧-alpha-D-半乳糖胺	methyl α-D-N-acetylgalactosamine	6082-22-0	C9H17NO6	235.237
  2-乙酰氨基-2-脱氧-D-吡喃半乳糖	N-acetyl-D-galactosamine	1136-42-1	C8H15NO6	221.21
  ——	Methyl 2-acetamido-2-deoxy-4,6-O-(p-methoxybenzylidene)-alpha-D-galactopyranoside	——	C17H23NO7	353.372
  ——	methyl 2-azido-4,6-benzylidene-2-deoxy-α-D-galactopyranoside	362651-60-3	C14H17N3O5	307.306

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	α-L-Fucp(1->2)-β-D-Galp-(1->3)-α-GalpNAc-OMe	848566-17-6	C21H37NO15	543.522

反应信息

• 作为反应物：
  描述：

  甲基 2-乙酰氨基-2-脱氧-3-O-(beta-D-吡喃半乳糖基)-alpha-D-吡喃半乳糖苷 在 三羟甲基氨基甲烷盐酸盐 GST fusion protein 、 WbnI protein 、 manganese(ll) chloride 、 1,4-二巯基-2,3-丁二醇 作用下， 反应 144.0h， 生成 α-L-Fucp-[α-D-Galp(1->3)](1->2)-β-D-Galp-(1->3)-α-GalpNAc-OMe
  参考文献：
  名称：

  Escherichia coli O86 O-Antigen Biosynthetic Gene Cluster and Stepwise Enzymatic Synthesis of Human Blood Group B Antigen Tetrasaccharide

  摘要：

  Previous study showed that some Gram-negative bacteria possess human blood group activity. Among them, Escherichia coli O86 has high blood group B activity and weak blood group A activity. This is due to the cell surface O-antigen structure, which resembles that of human blood group B antigen. In this study, we sequenced the entire E. coli O86 antigen gene cluster and identified all the genes responsible for O-antigen biosynthesis by sequence comparative analysis. The blood group B-like antigen in E. coli O86 O-polysaccharide was synthesized by sequentially employing three glycosyltransferases identified in the gene cluster. More importantly, we identified a new bacterial glycosyltransferase (WbnI) equivalent to human blood group transferase B (GTB). The enzyme substrate specificity and stepwise enzymatic synthesis of blood group B-like antigen revealed that the biosynthetic pathway of B antigen is essentially the same in E. coli O86 as in humans. This new finding provides a model to study the specificity and structure relationship of blood group transferases and supports the hypothesis of anti-blood group antibody production by bacterial stimulation.

  DOI：

  10.1021/ja045021y
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-D-半乳糖 在 吡啶 、 4 A molecular sieve 、 sodium 、 caesium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 33.25h， 生成 甲基 2-乙酰氨基-2-脱氧-3-O-(beta-D-吡喃半乳糖基)-alpha-D-吡喃半乳糖苷
  参考文献：
  名称：

  Bukowski, Ralph; Morris, Laura M.; Woods, Robert J., European Journal of Organic Chemistry, 2001, # 14, p. 2697 - 2705

  摘要：

  DOI：

文献信息

• Selective anomeric acetylation of unprotected sugars in water
  作者：David Lim、Antony J. Fairbanks

  DOI：10.1039/c6sc04667c

  日期：——

  High yielding selective acetylation of only the anomeric hydroxyl of unprotected sugars is possible in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), thioacetic acid, and a suitable base. The reaction, which may be performed on a multi-gram scale, is stereoselective for sugars that possess a hydroxyl group at position-2, exclusively yielding the 1,2-trans products. The use

  使用氯化 2-氯-1,3-二甲基咪唑啉鎓 (DMC)、硫代乙酸和合适的碱，可以在水溶液中仅对未受保护的糖的异头羟基进行高产率选择性乙酰化。该反应可以在数克规模上进行，对于在 2 位具有羟基的糖具有立体选择性，仅产生 1,2-反式产物。使用迭代试剂添加程序允许使用碳酸钠作为碱，避免形成可能妨碍产物纯化的三乙铵盐。乙酸糖基产物可用作糖苷酶催化合成的供体底物。粗水性乙酰化反应混合物也可用于此目的。
• Characterization of the Immobilized β-Galactosidase C from<i>Bacillus circulans</i>and the Production of β(1→3)-linked Disaccharides
  作者：Andreas NAUNDORF、Mylène CAUSSETTE、Katsumi AJISAKA

  DOI：10.1271/bbb.62.1313

  日期：1998.1

  β-galactosidase, which was obtained from the β-galactosidase C gene of Bacillus circulans and cleaves the non-reducing end galactosyl residue of β(1→3)-linkages selectively, was immobilized using CNBr-Sepharose. Although the effect of pH was not changed by the immobilization, the thermostability and stability in the presence of DMF were increased. Optimization of the transglycosylation using para-nitrophenyl β-D-galactopyranoside

  使用CNBr-琼脂糖固定化了一种重组β-半乳糖苷酶，该重组β-半乳糖苷酶是从环状芽孢杆菌的β-半乳糖苷酶C基因获得的，并选择性切割β（1→3）-键的非还原性半乳糖基残基。尽管固定化不会改变pH的影响，但在DMF存在下，其热稳定性和稳定性均得到提高。使用对硝基苯基β-D-吡喃半乳糖苷作为供体和苄基-α-DN-乙酰基半乳糖胺作为受体的转糖基化的最优化提供了以克规模合成的具有62％摩尔收率的β（1→3）连接的二糖衍生物。使用甲基类似物作为受体，将53％的受体转化为相应的β（1→3）-二糖。
• Subsequent Enzymatic Galactosylation and Sialylation Towards Sialylated Thomsen–Friedenreich Antigen Components
  作者：Lars Kröger、Agnes Scudlo、Joachim Thiem

  DOI：10.1002/adsc.200606063

  日期：2006.7

  by a facile synthesis of such motifs. Employing chemoenzymatic methods, several modified Galβ1-3GalNAc derivatives were synthesized. Modifications were introduced at the stage of the monomeric building blocks prior to formation of the disaccharides by means of four different β-galactosidases from bovine testes, Bacillus circulans and Xanthomonas manihotis as well as the phosphorylase from Bifidobacterium

  类型Neu5Acα2-3Galβ1的唾液酸低聚糖- 3GalNAc和一系列相应的图案起到本质的重要作用，并在神经节苷脂中发现的，刘易斯I型结构和高等动物，病毒，细菌，原生动物发生的唾液酸-汤姆森- Friedenreich抗原和致病真菌。有相当大的兴趣来评估这些糖结构的重要功能，在这里，我们通过轻松合成这些基序来提出一种化学酶法。利用化学酶法，合成了几种修饰的Galβ1-3GalNAc衍生物。在形成双糖之前，通过四种不同的牛睾丸，圆形芽孢杆菌和β-半乳糖苷酶，在单体结构单元的阶段引入了修饰。Xanthomonas manihotis以及双歧双歧杆菌的磷酸化酶。最后，可以使用来自克鲁斯锥虫的重组反式唾液酸酶有效地唾液酸化修饰的二糖衍生物。
• Synthesis of Mucin O‐Glycans Associated with Attenuation of Pathogen Virulence
  作者：Giulietta Minzer、Rachel Hevey

  DOI：10.1002/open.202200134

  日期：——

  Recent studies have reported that pooled mucin O-glycans attenuate virulence in diverse pathogens, but the molecular mechanisms have not yet been established. In this work, an optimized synthetic method is described to generate a small library of mucin O-glycans for biological evaluation of discrete structures.

  最近的研究报告称，混合的粘蛋白 O-聚糖可减弱多种病原体的毒力，但分子机制尚未确定。在这项工作中，描述了一种优化的合成方法，以生成一个小型粘蛋白 O-聚糖库，用于离散结构的生物学评估。
• [EN] MUCIN GLYCANS AS ANTIFUNGAL AGENTS<br/>[FR] GLYCANES DE MUCINE UTILISÉS EN TANT QU'AGENTS ANTIFONGIQUES
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2023183897A1

  公开（公告）日：2023-09-28

  The disclosure provides, in various embodiments, methods of treating fungal infections in subjects in need thereof, methods of attenuating virulence of fungi (e.g., in subjects in need thereof), and methods of inhibiting formation of fungal biofilms on surfaces (e.g., living or inert surfaces) with mucin glycans, tautomer, stereoisomer and/or pharmaceutically acceptable salts thereof. The disclosure further provides, in various embodiments, mucin glycan compositions, such as synthetic mucin glycans and defined mucin glycan compositions.

  本公开在各种实施方案中提供了治疗有需要的受试者真菌感染的方法、减弱真菌毒力的方法（例如在有需要的受试者中），以及用粘蛋白聚糖、同系物、立体异构体和/或其药学上可接受的盐抑制真菌生物膜在表面上（例如活表面或惰性表面）形成的方法。在各种实施方案中，本公开进一步提供了粘蛋白聚糖组合物，如合成粘蛋白聚糖和定义粘蛋白聚糖组合物。