5-(methoxycarbonyl)pentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside | 848828-27-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(methoxycarbonyl)pentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
• 英文别名: 5'-methoxycarbonylpentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
• CAS: 848828-27-3
• 化学式: C₂₀H₂₉N₃O₆
• 分子量: 407.467
• InChiKey: WUTKCRFNEGINSN-NSYSGPAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  122.98
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)pentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 5-methoxycarbonylpentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Immunogens from a synthetic hexasaccharide fragment of the O-SP of Vibrio cholerae O:1, serotype Ogawa

  摘要：

  The known 5-(methoxycarbonyl)pentyl alpha-glycoside of the hexasaccharide of Vibrio cholerae O:1, serotype Ogawa 24 was newly prepared. The efficiency of construction of the hexasaccharide from the disaccharide glycosyl acceptor 6 and each of the two tetrasaccharide glycosyl donors 16, and 18, as an alternative to the iterative coupling of the disaccharide glycosyl donor 7 with 6, was evaluated. Compound 24 was treated with each of hydrazine hydrate, ethylenediamine. and hexamethylenediamine to give ligands 25, 27, and 29, respectively, equipped with different linkers. Reaction of the foregoing compounds with squaric acid diethyl ester. and the reactions of the thus formed monoesters 26, 28, and 30 with BSA were evaluated. The rate of formation of the corresponding monoester was higher with hydrazide 25 than with amines 27 and 29. whose reaction rates were virtually the same. Reactions of squaric acid derivatives 26, 28, and 30 with BSA were conducted under the same conditions (reaction temperature, ligand-BSA ratio, and concentration with respect to the hapten) and targeted for neoglycoconjugates with 24-BSA ratio of similar to5. Monitoring the conversions by SELDI-TOF mass spectrometry in conjunction with the ProteinChip(R) system made it possible to conduct the conjugations in controlled fashion, and to terminate the reactions when the desired carbohydrate-protein ratios were reached. Products from 26, 28, and 30, neoglycoconjugates 31-33, containing 4.9, 5.0, and 5.1 moles of 24/BSA, respectively, were obtained in 87-93% yields. When the conjugation started with the initial molar carbohydrate-protein ratio of 15:1, the final molar carbohydrate-BSA ratio reached after 14 days with ligands 26, 28, and 30 was 9.0, 11.0, and 9.1, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.021
• 作为产物：
  描述：

  1,2-di-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-(methoxycarbonyl)pentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Immunogens from a synthetic hexasaccharide fragment of the O-SP of Vibrio cholerae O:1, serotype Ogawa

  摘要：

  The known 5-(methoxycarbonyl)pentyl alpha-glycoside of the hexasaccharide of Vibrio cholerae O:1, serotype Ogawa 24 was newly prepared. The efficiency of construction of the hexasaccharide from the disaccharide glycosyl acceptor 6 and each of the two tetrasaccharide glycosyl donors 16, and 18, as an alternative to the iterative coupling of the disaccharide glycosyl donor 7 with 6, was evaluated. Compound 24 was treated with each of hydrazine hydrate, ethylenediamine. and hexamethylenediamine to give ligands 25, 27, and 29, respectively, equipped with different linkers. Reaction of the foregoing compounds with squaric acid diethyl ester. and the reactions of the thus formed monoesters 26, 28, and 30 with BSA were evaluated. The rate of formation of the corresponding monoester was higher with hydrazide 25 than with amines 27 and 29. whose reaction rates were virtually the same. Reactions of squaric acid derivatives 26, 28, and 30 with BSA were conducted under the same conditions (reaction temperature, ligand-BSA ratio, and concentration with respect to the hapten) and targeted for neoglycoconjugates with 24-BSA ratio of similar to5. Monitoring the conversions by SELDI-TOF mass spectrometry in conjunction with the ProteinChip(R) system made it possible to conduct the conjugations in controlled fashion, and to terminate the reactions when the desired carbohydrate-protein ratios were reached. Products from 26, 28, and 30, neoglycoconjugates 31-33, containing 4.9, 5.0, and 5.1 moles of 24/BSA, respectively, were obtained in 87-93% yields. When the conjugation started with the initial molar carbohydrate-protein ratio of 15:1, the final molar carbohydrate-BSA ratio reached after 14 days with ligands 26, 28, and 30 was 9.0, 11.0, and 9.1, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.021

文献信息

• [EN] CAPPED OLIGOSACCHARIDES COMPRISING SEVEN OR MORE UNITS OF 4,6-DIDEOXY-4-ACYLAMIDO-ALPHA-PYRANOSE AND CONJUGATES THEREOF AS VACCINES AGAINST INFECTIONS CAUSED BY BRUCELLA ORGANISMS<br/>[FR] POLYSACCHARIDE ET PROCÉDÉS
  申请人：THE SEC DEP FOR ENVIRONMENT FOOD AND RURAL AFFAIRS

  公开号：WO2018083490A3

  公开（公告）日：2018-08-09
• Molecular Recognition of <i>Brucella</i> A and M Antigens Dissected by Synthetic Oligosaccharide Glycoconjugates Leads to a Disaccharide Diagnostic for Brucellosis
  作者：N. Vijaya Ganesh、Joanna M. Sadowska、Susmita Sarkar、Laurence Howells、John McGiven、David R. Bundle

  DOI：10.1021/ja5081184

  日期：2014.11.19

  The cell wall O-polysaccharides of pathogenic Brucella species are homopolymers of the rare sugar 4,6-dideoxy-4-formamido-alpha-D-mannopyranose. Despite the apparent simplicity of the polysaccharide it appears to be a "block copolymer" composed of A and M polysaccharide sequences expressed as a single molecule. The simultaneous presence of both in the cell wall has complicated the understanding of the molecular recognition of these antigens by antibodies present in the serum of infected animals and humans and by monoclonal antibodies. Since presumptive diagnosis of brucellosis, a serious disease in domestic livestock, wild animals, and humans, is based on detection of these antibodies it is important to separate the two antigenic epitopes, one of which is also found in other bacteria. Chemical synthesis provides the only means to achieve this outcome. A series of six oligosaccharides from di to hexasaccharides 1-6 were synthesized and conjugated to proteins to provide glycoconjugate antigens and conjugate vaccines. These chemically defined antigens identified the M antigenic determinant and provided a structural basis for understanding the fine specificity of monoclonal and polyclonal antibodies that bind the M antigen. This resulted in the discovery of a disaccharide that shows considerable potential as an unambiguous diagnostic antigen for detecting brucellosis in humans and animals and two hexasaccharide conjugate vaccine candidates that produce high levels of O-polysaccharide specific antibodies in mice.
• Synthesis and immunogenicity of Brucella monovalent neoglycoconjugate
  作者：Tiantian Hao、Haomeng Wang、Jiacheng Liu、Qian Zhang、Yuning Liu、Lianbo Zhao、Tao Zhu、Peng Yu、Na Guo、Xin Meng

  DOI：10.1016/j.carres.2020.108196

  日期：2021.1