α-L-Fucp(1->2)-β-D-Galp-(1->3)-α-GalpNAc-OMe | 848566-17-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-L-Fucp(1->2)-β-D-Galp-(1->3)-α-GalpNAc-OMe
• 英文别名: methyl α-L-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-α-D-galactopyranoside；Methyl alpha-L-fucopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-alpha-D-galactopyranoside；N-[(2S,3R,4R,5R,6R)-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamide
• CAS: 848566-17-6
• 化学式: C₂₁H₃₇NO₁₅
• 分子量: 543.522
• InChiKey: WXRMXXGTANSIIT-KRVGKYMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  246
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  尿苷 5’-二二氧磷基半乳糖二钠盐 、 α-L-Fucp(1->2)-β-D-Galp-(1->3)-α-GalpNAc-OMe 在 三羟甲基氨基甲烷盐酸盐 WbnI protein 、 manganese(ll) chloride 、 1,4-二巯基-2,3-丁二醇 作用下， 反应 72.0h， 以93%的产率得到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：

  O-甲基-N-乙酰基-2-脱氧-alpha-D-半乳糖胺 在 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 三氟甲磺酸三甲基硅酯 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 97.0h， 生成 α-L-Fucp(1->2)-β-D-Galp-(1->3)-α-GalpNAc-OMe
  参考文献：
  名称：

  与病原体毒力减弱相关的粘蛋白 O-聚糖的合成

  摘要：

  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。

  DOI：

  10.1002/open.202200134

文献信息

• [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。
• <i>Escherichia coli</i> O86 O-Antigen Biosynthetic Gene Cluster and Stepwise Enzymatic Synthesis of Human Blood Group B Antigen Tetrasaccharide
  作者：Wen Yi、Jun Shao、Lizhi Zhu、Mei Li、Mamata Singh、Yuquan Lu、Steven Lin、Hanfen Li、Kang Ryu、Jie Shen、Hongjie Guo、Qingjia Yao、C. Allen Bush、Peng G. Wang

  DOI：10.1021/ja045021y

  日期：2005.2.1

  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.
• 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。