p-nitrophenyl 4-O-α-D-galactopyranosyl-β-D-galactopyranoside | 80446-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 4-O-α-D-galactopyranosyl-β-D-galactopyranoside
• 英文别名: Gal(a1-4)Gal(b)-O-Ph(4-NO2)；(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 80446-81-7
• 化学式: C₁₈H₂₅NO₁₃
• 分子量: 463.395
• InChiKey: IAYJZWFYUSNIPN-OANJZRBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  224
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 4-O-α-D-galactopyranosyl-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-[4-[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]acetamide
  参考文献：
  名称：

  Structure–activity relationships of galabioside derivatives as inhibitors of E. coli and S. suis adhesins: nanomolar inhibitors of S. suis adhesins

  摘要：

  合成并评估了四种Galα1-4Gal衍生物作为产尿致病大肠杆菌PapG II类粘附素及链球菌豚型（Streptococcus suis）PN和PO粘附素的抑制剂。具有芳香结构的半乳糖双糖，特别是含有甲氧基苯基的O-半乳糖双糖，被确定为PapG粘附素的强效抑制剂。在半乳糖双糖的C3'位进行苯基脲衍生化，以及在O2'位进行甲氧基甲基化，提供了对S. suis PN型粘附素具有显著高亲和力的抑制剂（分别为30和50 nM）。此外，利用多变量数据分析方法建立了针对大肠杆菌PapG粘附素和S. suis PO型粘附素的定量构效关系模型。这些抑制剂的领先结构为开发高亲和力的潜在抗粘附治疗剂以靶向细菌感染提供了进展。

  DOI：

  10.1039/b416878j
• 作为产物：
  描述：

  1,2,3,6-tetra-O-benzoyl-α-D-galactopyranose 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 silver imidazolate 、 氢溴酸 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 zinc(II) chloride 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 2.0h， 生成 p-nitrophenyl 4-O-α-D-galactopyranosyl-β-D-galactopyranoside
  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

• 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。
• US4657849A
  申请人：——

  公开号：US4657849A

  公开（公告）日：1987-04-14
• US4762824A
  申请人：——

  公开号：US4762824A

  公开（公告）日：1988-08-09
• Synthesis of di- and tri-saccharides corresponding to receptor structures recognised by pyelonephritogenic E. coli fimbriae (pili)
  作者：Per J. Garegg、Hans Hultberg

  DOI：10.1016/0008-6215(82)84007-x

  日期：1982.12

  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.
• Structure–activity relationships of galabioside derivatives as inhibitors of E. coli and S. suis adhesins: nanomolar inhibitors of S. suis adhesins
  作者：Jörgen Ohlsson、Andreas Larsson、Sauli Haataja、Jenny Alajääski、Peter Stenlund、Jerome S. Pinkner、Scott J. Hultgren、Jukka Finne、Jan Kihlberg、Ulf J. Nilsson

  DOI：10.1039/b416878j

  日期：——

  Four collections of Galα1-4Gal derivatives were synthesised and evaluated as inhibitors of the PapG class II adhesin of uropathogenic Escherichia coli and of the PN and PO adhesins of Streptococcus suis strains. Galabiosides carrying aromatic structures at C1, methoxyphenyl O-galabiosides in particular, were identified as potent inhibitors of the PapG adhesin. Phenylurea derivatisation at C3′ and methoxymethylation at O2′ of galabiose provided inhibitors of the S. suis strains type PN adhesin with remarkably high affinities (30 and 50 nM, respectively). In addition, quantitative structure–activity relationship models for E. coli PapG adhesin and S. suis adhesin type PO were developed using multivariate data analysis. The inhibitory lead structures constitute an advancement towards high-affinity inhibitors as potential anti-adhesion therapeutic agents targeting bacterial infections.

  合成并评估了四种Galα1-4Gal衍生物作为产尿致病大肠杆菌PapG II类粘附素及链球菌豚型（Streptococcus suis）PN和PO粘附素的抑制剂。具有芳香结构的半乳糖双糖，特别是含有甲氧基苯基的O-半乳糖双糖，被确定为PapG粘附素的强效抑制剂。在半乳糖双糖的C3'位进行苯基脲衍生化，以及在O2'位进行甲氧基甲基化，提供了对S. suis PN型粘附素具有显著高亲和力的抑制剂（分别为30和50 nM）。此外，利用多变量数据分析方法建立了针对大肠杆菌PapG粘附素和S. suis PO型粘附素的定量构效关系模型。这些抑制剂的领先结构为开发高亲和力的潜在抗粘附治疗剂以靶向细菌感染提供了进展。