methyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 67561-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: methyl 4-O-[4'-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside；Methyl 4-O-[4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside；methyl 4-O-(4-O-α-D-galactopyranosyl-β-D-galactopyranosyl)-β-D-glucopyranoside；methyl globotrioside；Gal(a1-4)Gal(b1-4)b-Glc1Me；(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 67561-82-4
• 化学式: C₁₉H₃₄O₁₆
• 分子量: 518.469
• InChiKey: YHLYETOEEVCCRS-QMXNKGIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-4-O-<2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以86%的产率得到methyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of di- and tri-saccharides corresponding to receptor structures recognised by pyelonephritogenic E. coli fimbriae (pili)

  摘要：

  Syntheses are described of di- and tri-saccharides required for studies of the inhibition of adhesion by means of fimbriae of pyelonephritogenic E. coli bacteria to epithelium cells in the urinary tract containing suitable receptor sites. The disaccharides are the rho-nitrophenyl and methyl glycosides of 4-omicron-alpha-D-galactopyranosyl-beta-D-galactopyranose, and the trisaccharides are the rho-nitrophenyl and methyl glycosides of 4-omicron-(4-omicron-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-beta- D-glucopyranose. The key aglycons were the 1,2,3,6-tetrabenzoate of alpha-D-galactose and the 1,2,3,6,-2',3',6'-heptabenzoate of alpha-lactose. Glycosidations were performed with 2,3,4,6-tetra-omicron-benzyl-alpha-D-galactopyranosyl chloride as glycosylating agent and silver triflate as promoter.

  DOI：

  10.1016/0008-6215(82)84007-x

文献信息

• One-step synthesis of α-Gal epitope and globotriose derivatives by an engineered α-galactosidase
  作者：Lili Zhang、Lili Lu、Shuquan Fan、Lan Jin、Guofeng Gu、Li Xu、Min Xiao

  DOI：10.1039/c4ra16917d

  日期：——

  A novel method for synthesis of α-Gal epitope and globotriose derivatives by an engineered α-galactosidase through a one-enzyme one-step reaction.

  一种通过工程改造的α-半乳糖苷酶实现α-Gal表位和三糖衍生物合成的新方法，通过一酶一步反应实现。
• Composition for therapeutic or diagnostic use
  申请人：Källenius, Gunilla Petterson

  公开号：EP0035484A2

  公开（公告）日：1981-09-09

  Compositions for therapeutic or diagnostic use in connection with bacterial infections containing as an active constituent the structural element, preferably in terminal position: A process for the therapeutic treatment of mammals including man, comprising administering to the mammal an active amount of such a composition. A process for identification or quantification of such structural element in native biological ma'arial from mammals including man, comprising using antibodies, the generation of which has been initiated by such composition. A process for the identification of bacterial acceptor structures (pili, syn. fimbriae) recognizing the described structural element, comprising using this recognition. A process for purifying acceptor structures of bacteria, comprising using for the purification the affinity between such structural element and the corresponding acceptor structures on the bacteria. A method of diagnosing mammals including man in regard to proneness to bacterial infection involving such receptor structure, comprising generating anti- bodies against said receptor structure and recording the reaction of said antibodies and cells from the mammal.

  用于治疗或诊断细菌感染的复合物，其中含有作为活性成分的结构元素，最好位于末端位置： 一种对哺乳动物（包括人类）进行治疗的方法，包括向哺乳动物施用有效量的这种组合物。一种鉴定或量化哺乳动物（包括人类）原生生物体内这种结构元素的方法，包括使用由这种组合物引发的抗体。一种识别细菌接受体结构（纤毛虫，同义；fimbriae）的方法，包括利用这种识别。一种纯化细菌受体结构的方法，包括利用这种结构元素与细菌上相应的受体结构之间的亲和力进行纯化。一种诊断哺乳动物（包括人类）是否易受涉及上述受体结构的细菌感染的方法，包括产生针对上述受体结构的抗体，并记录上述抗体与哺乳动物细胞的反应。
• A new one-pot synthesis of Gb3 and isoGb3 trisaccharide analogues
  作者：Changning Wang、Qin Li、Haisheng Wang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1016/j.tet.2006.09.058

  日期：2006.12

  Gb(3) and isoGb(3) are both biologically important oligosaccharides. A new efficient synthesis of Gb(3) and isoGb(3) trisaccharide analogues has been achieved by one-pot sequential glycosylation strategy starting from simple monosaccharide building blocks promoted by N-(phenylthio)-epsilon-caprolactam at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.
• Efficient chemoenzymatic synthesis of globotriose and its derivatives with a recombinant α-(1→4)-galactosyltransferase
  作者：Jianbo Zhang、Przemyslaw Kowal、Jianwen Fang、Peter Andreana、Peng George Wang

  DOI：10.1016/s0008-6215(02)00106-4

  日期：2002.6

  A truncated alpha-(1-->4)-galactosyltransferase (LgtC) gene from Neisseria meningitidis was cloned. The recombinant glycosyltransferase was expressed in Escherichia coli BL21 (DE3) strain with high specific activity (5 units/mg protein). Its acceptor specificity was carefully characterized. Then the purified enzyme was utilized in highly efficient syntheses of globotriose and a variety of alpha-(1-->4)-galactosylated derivatives as potential antibacterial agents. (C) 2002 Published by Elsevier Science Ltd.
• US4657849A
  申请人：——

  公开号：US4657849A

  公开（公告）日：1987-04-14