3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl bromide | 68733-29-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl bromide
• 英文别名: [(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-bromooxan-2-yl]methyl acetate
• CAS: 68733-29-9
• 化学式: C₁₂H₁₆BrN₃O₇
• 分子量: 394.179
• InChiKey: MSEDCODCCLBQJH-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-(Z-氨基)-1-己醇 、 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl bromide 在 2,4,6-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 (6-(benzyloxycarbonylamino)hexyl) 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside 、 (6-(benzyloxycarbonylamino)hexyl) 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Phosphorylcholine−Carbohydrate− Protein Conjugates Efficiently Induce Hapten-Specific Antibodies Which Recognize Both Streptococcus pneumoniae and Neisseria meningitidis:  A Potential Multitarget Vaccine against Respiratory Infections

  摘要：

  Phosphoryleholine (ChoP) is commonly expressed at the surface of pathogens of the respiratory tract, including Streptococcus pneumoniae and Neisseria meningitidis. We designed a synthetic hapten comprising ChoP and part of its native carrier structure in S. pneumoniae, i.e. N-acetyl-D-galactosamine (GalNAc). Protein conjugates of this hapten induced GaINAc-ChoP-specific antibodies which recognized Chol? on both S. pneumoniae and N. meningitidis. GalNAc-ChoP could therefore lead to the rational design of a novel multipurpose vaccine against respiratory infections.

  DOI：

  10.1021/jm040783p
• 作为产物：
  描述：

  1,2,3,4,6-戊-O-乙酰-a-D-吡喃半乳糖 在 N-甲基咪唑 、 sodium azide 、 ammonium cerium(IV) nitrate 、 氢溴酸 、 溶剂黄146 、 lithium bromide 、 锌 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 9.5h， 生成 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl bromide
  参考文献：
  名称：

  Phosphorylcholine−Carbohydrate− Protein Conjugates Efficiently Induce Hapten-Specific Antibodies Which Recognize Both Streptococcus pneumoniae and Neisseria meningitidis:  A Potential Multitarget Vaccine against Respiratory Infections

  摘要：

  Phosphoryleholine (ChoP) is commonly expressed at the surface of pathogens of the respiratory tract, including Streptococcus pneumoniae and Neisseria meningitidis. We designed a synthetic hapten comprising ChoP and part of its native carrier structure in S. pneumoniae, i.e. N-acetyl-D-galactosamine (GalNAc). Protein conjugates of this hapten induced GaINAc-ChoP-specific antibodies which recognized Chol? on both S. pneumoniae and N. meningitidis. GalNAc-ChoP could therefore lead to the rational design of a novel multipurpose vaccine against respiratory infections.

  DOI：

  10.1021/jm040783p

文献信息

• Stereoselectivity of glycosylation with derivatives of 2-azido-2-deoxy-d-galactopyranose. The synthesis of a determinant oligosaccharide related to blood-group a (type 1)
  作者：Nikolai V. Bovin、Sergei É. Zurabyan、Anatoly Ya. Khorlin

  DOI：10.1016/0008-6215(83)88263-9

  日期：1983.1

  6-tri-O-benzyl-2-deoxy-β- d -galactopyranosyl chloride (9) was found to be the most efficient glycosylating agent for the synthesis of oligosaccharides containing 2-acetamido-2-deoxy-α- d -galactopyranose residues, and gave a tetrasaccharide, which is a determinant of the blood-group A (Type 1), i.e., O-α- l -fucopyranosyl-(1→2)-[O-2-acetamido-2-deoxy-α- d - galactopyranosyl-(1→3)]-O-β- d -galactopyr

  摘要在各种条件下，研究了2-叠氮基-2-脱氧-d-吡喃半乳糖衍生物对模型醇（环己醇）的立体选择性糖基化作用。发现2-叠氮基-3,4,6-三-O-苄基-2-脱氧-β-d-吡喃半乳糖基氯（9）是用于合成含有2-acetamido-2-的寡糖的最有效的糖基化剂脱氧-α-d-吡喃半乳糖残基，得到四糖，它是A型血型（1型）的决定因素，即O-α-1-呋喃核糖基-（1→2）-[O-2-乙酰氨基-2-脱氧-α-d-吡喃半乳糖-（1→3）]-O-β-d-吡喃半乳糖-（1→3）-2-乙酰氨基-2-脱氧-d-葡萄糖及其三糖片段， O-2-乙酰氨基-2-脱氧-α-d-半乳糖吡喃糖基-（1→3）-O-β-d-吡喃半乳糖基-（1→3）-2-乙酰胺基-2-脱氧-d-葡萄糖。在这个综合过程中，
• Ultrasonic Agitation Accelerates cis-Glycosylation with Heterogeneous Promoters
  作者：Dennis M. Whitfield、M. Younus Meah、Jiří J. Křepinský

  DOI：10.1135/cccc19930159

  日期：——

  Ultrasonic agitation increases the yield of glycosylations with donors such as 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl chloride using the heterogeneous promoters silver zeolite, cadmium zeolite or a mixture of silver perchlorate and silver carbonate on celite. The stereospecificity of the glycosylation depends on the nature of the alcohol to be glycosylated, the nature of the solid support and the solvent. Glycosylation catalyzed by silver zeolite in toluene solutions of the donor 3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-β-D-glucopyranosyl bromide, that usually produce trans-β-glycosides, yield cis-glycosides with unreactive alcohols. In these unreactive alcohols, e.g. methyl 2-O-benzoyl-4,6-O-benzilidene-β-D-galactopyranoside and benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside, the hydroxyls to be glycosylated are hydrogen-bonded to a cis vicinal oxygen. This feature was evident in their AM1 minimized conformations and was indicated by the solution J(OH,CH) ¹H NMR coupling constants.

  超声波激发可以增加异相促进剂银沸石、镉沸石或银高氯酸盐和碳酸银混合物在硅藻土上使用3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-α-D-半乳糖苷氯化物等供体进行糖基化的产率。糖基化的立体特异性取决于要糖基化的醇的性质、固体支持和溶剂的性质。在甲苯溶液中，银沸石催化的供体3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-葡萄糖苷溶液通常产生trans-β-糖苷，而在不活泼的醇中产生cis-糖苷。在这些不活泼的醇中，例如甲基2-O-苯甲酰基-4,6-O-苯甲亚甲基-β-D-半乳糖苷和苄基3,4,6-三-O-苯甲基-α-D-甘露糖苷，要糖基化的羟基与一个cis邻接氧原子形成氢键。这个特征在它们的AM1最小化构象中是明显的，并且由溶液J(OH,CH) ¹H NMR偶合常数指示。
• Stereoselectivity in glycosylation by means of 2-azido-2-desoxy-D-galactopyranose derivatives and the synthesis of the determinative oligosaccharide of blood group A, type 1
  作者：N. V. Bovin、S. �. Zurabyan、A. Ya. Khorlin

  DOI：10.1007/bf00949960

  日期：1982.5
• [EN] CARBOHYDRATE-PHOSPHORYLCHOLINE CONJUGATE MOLECULES AND THEIR USE IN VACCINAL, THERAPEUTIC AND DIAGNOSTIC APPLICATIONS<br/>[FR] MOLECULES DE CONJUGUES DE CARBOHYDRATE-PHOSPHORYLCHOLINE ET LEUR UTILISATION DANS DES APPLICATIONS VACCINALES, THERAPEUTIQUES ET DIAGNOSTIQUES
  申请人：PASTEUR INSTITUT

  公开号：WO2006003518A2

  公开（公告）日：2006-01-12

  The present invention relates to carbohydrate-phosphorylcholine conjugate molecule, and more particularly to phosphorylcholine-N-acetyl-D-galactosamine molecules and their use for treating and/or preventing a bacterial infection of the respiratory tract. More specifically, in this present application, the inventors aimed at raising high-affinity antibodies against ChoP preferably in its bacterial context in order to target several pathogens of the respiratory tract. By mimicking the S. pneumoniae model, the inventors preferably synthesized two carbohydrate-ChoP (GalNAc-ChoP) protein conjugates and showed that these immunogens induce hapten-specific antibodies which recognize two major bacterial pathogens of the respiratory tract : such as a Gram-positive bacterium, S. pneumoniae, and a Gram-negative bacterium, N. meningitidis.