methyl [(3,5-dideoxy-5-acetamido-D-glycero-α-D-gulo-non-2-ulopyranosid)onic acid](2→3)β-D-galactopyranoside | 100605-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [(3,5-dideoxy-5-acetamido-D-glycero-α-D-gulo-non-2-ulopyranosid)onic acid](2→3)β-D-galactopyranoside
• 英文别名: methyl (5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-nonulopyranosylonic acid)-(2-6)-β-D-galactopyranoside；methyl 6-O-(N-acetyl-α-D-neuraminate-2-yl)-β-D-glucopyranoside；α-D-NeuAc-(2->6)-β-D-Gal-O-Me；NeuAc(a2-6)b-Gal1Me；(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 100605-28-5
• 化学式: C₁₈H₃₁NO₁₄
• 分子量: 485.442
• InChiKey: SYRRNWXUCFJYME-SRSYBPMMSA-N

物化性质

• 沸点：
  926.9±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  methyl (1-adamantanyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 在 吡啶 、 5%-palladium/activated carbon 、 氢气 、 sodium isopropylate 、 溶剂黄146 、 barium(II) hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 2,2,2-三氟乙醇 、 水 、 异丙醇 、 乙腈 为溶剂， -78.0~60.0 ℃ 、101.33 kPa 条件下， 反应 35.3h， 生成 methyl [(3,5-dideoxy-5-acetamido-D-glycero-α-D-gulo-non-2-ulopyranosid)onic acid](2→3)β-D-galactopyranoside
  参考文献：
  名称：

  与假氨基酸苷相关的 5-epi-α-Sialoside 的立体选择性合成。 5-叠氮基-5-去乙酰氨基唾液酸硫代糖苷立体选择性的重新评估以及三氟甲磺酸酯作为亲核试剂在唾液酸 Zbiral 脱氨中的应用

  摘要：

  为了最终合成用于立体控制合成假氨基酸糖苷的糖基供体，描述了在5-位携带轴向叠氮化物的d-甘油-d-古洛糖唾液酸金刚烷基硫糖苷的立体控制合成。该合成采用乙酰丙酸作为亲核试剂，对N-乙酰神经氨酸硫代糖苷进行氧化脱氨，从而形成选择性保护为 5- O的 3-脱氧-d-甘油-d-半乳糖-2-nonulosonic 酸 (KDN) 衍生物-乙酰丙酸。用三氟甲磺酸酯替代乙酰丙酸酯能够引入轴向叠氮化物，从而形成糖基供体。当直接获得 5- O-三氟甲磺酸基 KDN 衍生物时，更短的合成在氧化脱氨步骤中使用三氟甲磺酸盐作为亲核试剂。在-78℃下用5-叠氮基-d-甘油-d- gulo配置的唾液酸金刚烷基硫代糖苷进行的糖基化反应对于赤道糖苷的形成具有选择性，这表明赤道伪胺酸糖苷的合成将有可能作为合适的供体变得可用。还发现在 5 位带有赤道叠氮化物的类似N-乙酰神经氨酸金刚烷硫糖苷在相同条件下对赤道糖苷形成具有选择

  DOI：

  10.1021/acs.joc.6b02221

文献信息

• Chemoenzymatic Synthesis of Sialyl Oligosaccharides with Sialidases Employing Transglycosylation Methodology
  作者：Dirk Schmidt、Bernd Sauerbrei、Joachim Thiem

  DOI：10.1021/jo000871r

  日期：2000.12.1

  disease virus show a distinct preference for alpha(2-3) directed sialylations. Using combined chemical and enzymatic methodologies structures such as T-(Thomsen-Friedenreich) antigen [beta-D-Gal-(1-3)-alpha-D-GalNAc-OThr], Tn-(Thomsen nouveau) antigen (alpha-D-GalNAc-OThr) and beta-D-Gal-(1-4)-alpha-D-2-deoxy-Gal-OMe were sialylated in alpha(2-3)- and alpha(2-6)-positions regioselectively or in high

  利用霍乱弧菌，产气荚膜梭菌，鼠伤寒沙门氏菌和新城疫病毒的唾液酸酶的转糖活性，合成了一系列唾液寡糖。根据它们的水解活性，霍乱弧菌和产气荚膜梭菌的唾液酸酶优先催化唾液酸α（2-6）-键的形成，而伤寒沙门氏菌和新城疫病毒的唾液酸酶对α（2-3）表现出明显的偏爱。 ）定向唾液酸化。使用诸如T-（Thomsen-Friedenreich）抗原[β-D-Gal-（1-3）-α-D-GalNAc-OThr]的化学和酶学组合方法，在α（2-3）-中将Tn-（Thomsen nouveau）抗原（α-D-GalNAc-OThr）和β-D-Gal-（1-4）-α-D-2-脱氧-Gal-OMe唾液酸化。和α（2-6）-位置选择性或高区域异构体过量，并通过简单的分离程序纯化。取决于酶源和受体结构，转唾液酸化的产率在10％至30％之间变化。
• Mass Production of Bacterial α2,6-Sialyltransferase and Enzymatic Syntheses of Sialyloligosaccharides
  作者：Takeshi YAMAMOTO、Hideki NAGAE、Yasuhiro KAJIHARA、Ichiro TERADA

  DOI：10.1271/bbb.62.210

  日期：1998.1

  JT0160 cells as an enzyme source, enzymatic syntheses were performed with mono- and di-saccharides as the sialyl acceptors. It was clarified that a crude extract of P. damsela JT0160 cells can be used as an synthetic catalyst for the enzymatic synthesis of sialyloligosaccharides. Furthermore, the enzyme assay showed that sialyltransferase 0160 could transfer NeuAc to not only N-linked but also O-linked

  为了提供用于大规模合成唾液酸苷的α2,6-唾液酸转移酶，我们研究了生产唾液酸转移酶0160的培养条件。添加半乳糖和牛肉提取物以及控制培养基的pH值对生产有效唾液酸转移酶0160的最大产量。最大酶生产率达到550单位/ L。使用丹参光细菌JT0160细胞的粗提物作为酶源，以单糖和二糖为唾液酸受体进行酶促合成。已阐明，可以将P.damsela JT0160细胞的粗提物用作酶促合成唾液酸低聚糖的合成催化剂。此外，该酶分析表明，唾液酸转移酶0160不仅可以将NeuAc转移至N-连接的碳水化合物链，还可以将其转移至O-连接的碳水化合物链。
• Design and synthesis of a multivalent homing device for targeting to murine CD22
  作者：Leo A.J.M. Sliedregt、Sabine M.W. van Rossenberg、Reshma Autar、A.Rob P.M. Valentijn、Gijs A. van der Marel、Jacques H. van Boom、Christina Piperi、P. Anton van der Merwe、Johan Kuiper、Theo J.C. van Berkel、Erik A.L. Biessen

  DOI：10.1016/s0968-0896(00)00224-8

  日期：2001.1

  CD22 is a cell-surface glycoprotein uniquely located on mature B-cells and B-cell derived tumour cells. Current evidence suggests that binding of endogenous ligands to CD22 leads to modulation of B-cell activation by antigen. Incidentally, however, B-cell activation may derail, and lead to an undesired immune response, for example in cases of allergy, rheumatoid arthritis and Crohn's disease. In this situation, synthetic high-affinity ligands for CD22 may be of therapeutic value as inhibitors of B-cell activation. Recent studies have revealed that natural ligands for CD22 contain the trisaccharide NeuAc alpha -2,6-Lac as the basic binding motif. In addition, it has been demonstrated that binding to CD22 is strongly enhanced by multivalent presentation of the basic binding motif (cluster effect). In this paper, the stepwise development of a novel multivalent high-affinity ligand for CD22 is described. In the first stage, a series of monovalent NeuAc alpha -2,6-Glc(Y)X type binding motifs was prepared, and their affinity for murine CD22 was monitored, to obtain more insight into the effect of separate structure elements on ligand recognition. In the second stage, we prepared a trivalent cluster, based on the monovalent motif that displayed the highest affinity for CD22, NeuAccc2,6-GlcNBzNO(2)OMe (7). This cluster, TRIS(NeuAc alpha -2,6-GlcNBzNO(2))(3) (52), displayed a more than 58-fold higher affinity for CD22 than the reference structure NeuAc alpha -2,6-LacOMe (10). To our knowledge, the cluster 52 is one of the most potent antagonists for CD22, yet synthesised. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Thiem, Joachim; Sauerbrei, Bernd, Angewandte Chemie, 1991, vol. 103, # 11, p. 1521 - 1523
  作者：Thiem, Joachim、Sauerbrei, Bernd

  DOI：——

  日期：——
• Stereoselective Synthesis of 5-<i>epi</i>-α-Sialosides Related to the Pseudaminic Acid Glycosides. Reassessment of the Stereoselectivity of the 5-Azido-5-deacetamidosialyl Thioglycosides and Use of Triflate as Nucleophile in the Zbiral Deamination of Sialic Acids
  作者：Bibek Dhakal、Szymon Buda、David Crich

  DOI：10.1021/acs.joc.6b02221

  日期：2016.11.18

  With a view to the eventual synthesis of glycosyl donors for the stereocontrolled synthesis of pseudaminic acid glycosides, the stereocontrolled synthesis of a d-glycero-d-gulo sialic acid adamantanylthioglycoside carrying an axial azide at the 5-position is described. The synthesis employs levulinic acid as nucleophile in the oxidative deamination of an N-acetylneuraminic acid thioglycoside leading

  为了最终合成用于立体控制合成假氨基酸糖苷的糖基供体，描述了在5-位携带轴向叠氮化物的d-甘油-d-古洛糖唾液酸金刚烷基硫糖苷的立体控制合成。该合成采用乙酰丙酸作为亲核试剂，对N-乙酰神经氨酸硫代糖苷进行氧化脱氨，从而形成选择性保护为 5- O的 3-脱氧-d-甘油-d-半乳糖-2-nonulosonic 酸 (KDN) 衍生物-乙酰丙酸。用三氟甲磺酸酯替代乙酰丙酸酯能够引入轴向叠氮化物，从而形成糖基供体。当直接获得 5- O-三氟甲磺酸基 KDN 衍生物时，更短的合成在氧化脱氨步骤中使用三氟甲磺酸盐作为亲核试剂。在-78℃下用5-叠氮基-d-甘油-d- gulo配置的唾液酸金刚烷基硫代糖苷进行的糖基化反应对于赤道糖苷的形成具有选择性，这表明赤道伪胺酸糖苷的合成将有可能作为合适的供体变得可用。还发现在 5 位带有赤道叠氮化物的类似N-乙酰神经氨酸金刚烷硫糖苷在相同条件下对赤道糖苷形成具有选择