(8-Methoxycarbonyloctyl)-<2-acetamido-2-desoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosid> | 79063-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8-Methoxycarbonyloctyl)-<2-acetamido-2-desoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosid>
• 英文别名: 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside；β-D-Galp-(1->3)-α-D-GalpNAc-O(CH2)8CO2Me；8-methoxycarbonyloctyl-2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside；8-Methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-alpha-D-galactopyranoside；methyl 9-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxynonanoate
• CAS: 79063-80-2
• 化学式: C₂₄H₄₃NO₁₃
• 分子量: 553.604
• InChiKey: QCWPROARBPOGDI-IJHJDGDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (8-Methoxycarbonyloctyl)-<2-acetamido-2-desoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosid> 在 sodium hydroxide 作用下， 生成 8-Hydroxycarbonyloctyl 2-acetamido-2-deoxy-3-0-(β-D-galactopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of tumor antigenic determinant

  摘要：

  提供了用于合成人类T抗原决定因子2-乙酰胺基-2-脱氧-3-O-(β-D-半乳糖苷)-α-D-半乳糖苷的过程，其中包含一个α-O-糖苷键连接的桥接臂O-(CH2)nCOR。该决定因子与载体分子偶联形成人工T抗原，并与不溶性支持物相结合形成T免疫吸附剂。人工T抗原被证明能引起延迟型超敏反应，作为诊断人类癌症存在的一种方法。

  公开号：

  US04767845A1
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 在 palladium on activated charcoal 四氢呋喃 、 calcium sulfate 、 氢气 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 85.03h， 生成 (8-Methoxycarbonyloctyl)-<2-acetamido-2-desoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosid>
  参考文献：
  名称：

  Synthesis of the T [β-d-Gal-(1→3)-α-d-GalNAc]-antigenic determinant in a form useful for the preparation of an effective artificial antigen and the corresponding immunoadsorbent

  摘要：

  The T antigenic determinant was synthesized in the form 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-alpha-D-galactopyranoside (6) (beta-D-Gal-(1 goes to 3)-alpha-D-GalNAcO(CH2)8CO2Me). This T-hapten was used to prepare a T-BSA artificial antigen (7) and an immunoadsorbent (8), which were shown to possess the expected immunological properties. Nuclear Overhauser enhancements of the signals for anti-periplanar H-2' and the syn-axial H-3' of the beta-D-galactopyranosyl group were observed on saturation of H-1'. The signal for H-3 of the 2-acetamido-2-deoxy-alpha-D-galactopyranoside residue was also enhanced.

  DOI：

  10.1016/s0008-6215(00)80750-8

文献信息

• Use of the “core-2”-N-acetylglucosaminyltransferase in the chemical-enzymatic synthesis of a sialyl-Lex-containing hexasaccharide found on O-linked glycoproteins
  作者：Reinhold Oehrlein、Ole Hindsgaul、Monica M. Palcic

  DOI：10.1016/0008-6215(93)80011-3

  日期：1993.5

  obtained in a single step of affinity chromatography is suitable for use in preparative oligosaccharide synthesis. In conjunction with previously described preparations of beta-(1-->4)-galactosyltransferase (EC 2.4.1.22), alpha-(2-->3)-sialytransferase (EC 2.4.99.6) and alpha-(1-->3/4)-fucosyltransferase (EC 2.4.1.65), the GlcNAcT was used in the first step of a sequence which converted the disaccharide

  简单制备“核心II” N-乙酰氨基葡萄糖氨基转移酶（UDP-D-GlcpNAc：beta-D-Galp-（1-> 3）-alpha-D-GalpNAc（从GlcNAc到GalNAc）beta-（1-报道了来自商业小鼠肾丙酮粉的> 6）-GlcNAc-转移酶，GlcNAcT，EC 2.4.1.102）。在亲和层析的单个步骤中获得的酶适用于制备寡糖的合成。与先前描述的β-（1-> 4）-半乳糖基转移酶（EC 2.4.1.22），α-（2-> 3）-唾液酸转移酶（EC 2.4.99.6）和α-（1-> 3/4）-岩藻糖基转移酶（EC 2.4.1.65），GlcNAcT用于将双糖β-D-Galp-（1-> 3）-alpha-D-GalpNAc-OR转化为含唾液酸基LeX的结构alpha-D-NeupAc-（2-> 3）-beta-D-Galp-（1-> 4）-[alpha-L-Fucp-（1--
• Blocksynthese von O-glycopeptiden und anderen T-antigen strukturen
  作者：Hans Paulsen、Michael Paal

  DOI：10.1016/0008-6215(84)85006-5

  日期：1984.12

  Abstract Under the conditions of in situ anomerisation, the 2-azido-4,6-di- O -benzoyl-2-deoxy-3- O -(2,3,4,6-tetra- O -acetyl-β- d -galactopyranosyl)-α- d -galactopyranosyl bromide reacted directly and with high selectivity with the reactive hydroxyl groups of l -serine and l -threonine derivatives to form α-glycosidically-linked products. Thus, the glycopeptides containing l -serine and l -threonine

  摘要在原位异构化条件下，2-叠氮基-4,6-二-O-苯甲酰基-2-脱氧-3-O-（2,3,4,6-四-O-乙酰基-β-d -（半乳糖吡喃糖基）-α-d-半乳糖吡喃糖基溴与1-丝氨酸和1-苏氨酸衍生物的反应性羟基高选择性地直接反应，形成α-糖苷连接的产物。因此，更容易获得包含1-丝氨酸和1-苏氨酸的糖肽。二糖嵌段也可以与其他反应性羟基化合物偶联，以得到包含T受体的化合物。
• Method to detect T-antigen delayed hypersensitivity
  申请人：Chembiomed Ltd.

  公开号：US04855126A1

  公开（公告）日：1989-08-08

  Processes are provided for the synthesis of the human T-antigenic determinant 2-acetamido-2-deoxy-3-O-(.beta.-D-galactopyranosyl)-.alpha.-D-galactopyran oside containing an .alpha.-O-glycosidically linked bridging arm O--(CH.sub.2).sub.n COR. The determinant is coupled to carrier molecules to form artificial T-antigens, and to insoluble supports to form T-immunoadsorbents. The artificial T-antigen is shown to elicit a delayed type hypersensitivity reaction as a diagnostic for the presence of cancer in humans.

  提供了用于合成人类T-抗原决定因子2-乙酰胺基-2-脱氧-3-O-(β-D-半乳糖苷)-α-D-半乳糖苷的过程，其中包含一个α-O-糖苷键连接的桥接臂O-(CH2)nCOR。该决定因子与载体分子偶联形成人工T-抗原，并与不溶性支持物质结合形成T-免疫吸附剂。已证明人工T-抗原能引起延迟型超敏反应，作为诊断人类癌症存在的指标。
• US4767845A
  申请人：——

  公开号：US4767845A

  公开（公告）日：1988-08-30
• US4794176A
  申请人：——

  公开号：US4794176A

  公开（公告）日：1988-12-27