3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranose | 210295-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranose
• 英文别名: 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranose；(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranoside；Man2Ac3Ac4Ac6Ac(a1-2)a-Man3Ac4Ac6Ac；[(2R,3R,4S,5S,6S)-3,4-diacetyloxy-6-hydroxy-5-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 210295-12-8
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: KUORIMMMEVXGFY-AODGUXGTSA-N

物化性质

• 沸点：
  659.4±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  232.02
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranose 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-O-(5-isothiocyanato-3-oxapentyl)-3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranose
  参考文献：
  名称：

  Cyanovirin-N binding to Manα1–2Man functionalized dendrimers

  摘要：

  我们合成了甘露糖功能化的G(3)和G(4)-PAMAM树枝状聚合物，并通过MALDI-TOF MS和NMR光谱对其进行了表征。沉淀试验评估了二甘露糖官能化树枝状聚合物与 Cyanovirin-N 的结合情况，Cyanovirin-N 是一种通过高甘露糖介导的相互作用阻断病毒与细胞融合的 HIV 灭活蛋白。

  DOI：

  10.1039/b417789d
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基吡喃己糖 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二甲胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.5h， 生成 3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranose
  参考文献：
  名称：

  Synthesis of the Tetrasaccharide Cap Domain of the Antigenic Lipophosphoglycan of Leishmania donovani Parasite

  摘要：

  In this paper we report a new synthesis of the immunologically important tetrasaccharide terminal cap domain [Galp(1--4)-beta[Manp-( 1-2)-alpha-Manp-(1-2)-alpha]-Manp] of lipophosphoglycan (LPG); the major cell surface GPI molecule and key virulence factor of the protozoan parasite Leishmania donovani. The synthetic approach provided a short convergent route for the LPG cap motif from lactose and mannose starting materials. The synthesis was then applied for the preparation of a radiolabelled cap epitope for macrophage receptor binding and immunological studies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00609-8

文献信息

• <i>N</i> ‐Carboxyanhydride Polymerization of Glycopolypeptides That Activate Antigen‐Presenting Cells through Dectin‐1 and Dectin‐2
  作者：Matthew N. Zhou、Corleone S. Delaveris、Jessica R. Kramer、Justin A. Kenkel、Edgar G. Engleman、Carolyn R. Bertozzi

  DOI：10.1002/anie.201713075

  日期：2018.3.12

  and synthesized the first chemically defined ligands for dectin-1 and dectin-2. They comprised glycopolypeptides bearing mono-, di-, and trisaccharides and were built through polymerization of glycosylated N-carboxyanhydrides. Through this approach, we achieved glycopolypeptides with high molecular weights and low dispersities. We identified structures that elicit a pro-inflammatory response through

  C 型凝集素 dectin-1 和 dectin-2 通过识别它们的外来聚糖结构，有助于针对微生物病原体的先天免疫。这些受体是疫苗开发和癌症免疫治疗的有希望的靶标。然而，目前可用的激动剂是来自天然来源的异质糖缀合物和多糖。在这里，我们设计并合成了第一个化学定义的 dectin-1 和 dectin-2 配体。它们包含带有单糖、二糖和三糖的糖多肽，并通过糖基化的 N-羧酸酐的聚合而构建。通过这种方法，我们获得了高分子量和低分散性的糖多肽。我们确定了通过抗原呈递细胞中的 dectin-1 或 dectin-2 引发促炎反应的结构。
• DNA-Templated Homo- and Heterodimerization of Peptide Nucleic Acid Encoded Oligosaccharides that Mimick the Carbohydrate Epitope of HIV
  作者：Katarzyna Gorska、Kuo-Ting Huang、Olivier Chaloin、Nicolas Winssinger

  DOI：10.1002/anie.200903328

  日期：2009.9.28

  hybridization has been utilized to generate a combinatorial library of structures that emulate the topologies of complex carbohydrates interacting with an antibody that shows broad‐spectrum activity against HIV. This simple method involves attaching oligosaccharides tagged with peptide nucleic acids onto DNA templates in a controlled manner (see schematic picture).

  全部受控制：杂交的可编程性已用于生成结构的组合文库，该文库模拟复杂碳水化合物与抗体相互作用的拓扑结构，该抗体显示出针对HIV的广谱活性。这种简单的方法涉及以受控方式将标记有肽核酸的寡糖附着到DNA模板上（请参见示意图）。
• Synthesis of Mannosylglycerate Derivatives as Immunostimulating Agents
  作者：Nadège Hamon、Caroline C. Mouline、Marion Travert

  DOI：10.1002/ejoc.201700682

  日期：2017.9.1

  Analogues of mannosylglycerate have been synthesised and evaluated as immunostimulating agents.

  已经合成了甘露糖基甘油酸酯的类似物并评价为免疫刺激剂。
• Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains
  作者：Ichiro Matsuo、Megumi Isomura、Tatsuo Miyazaki、Tohru Sakakibara、Katsumi Ajisaka

  DOI：10.1016/s0008-6215(97)10001-5

  日期：1997.12

  Synthetic routes are described to a partial structure common to all high mannose-type sugar chains and complex-type sugar chains based on a chemoenzymatic strategy which incorporates, (a) enzymatic synthesis of oligosaccharide blocks using glycosidases, and (b) chemical synthesis of the branching oligosaccharides via regioselective coupling. All reaction products correspond to key intermediates necessary for the construction of N-linked oligosaccharides and we have synthesized the branched tetra-manno-oligosaccharide high mannose-type sugar chain and the branched hexa-oligosaccharide complex-type sugar chain using this simple and direct method. (C) 1998 Elsevier Science Ltd.
• Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
  作者：Alison M. Daines、Ben W. Greatrex、Colin M. Hayman、Sarah M. Hook、Warren T. McBurney、Thomas Rades、Phillip M. Rendle、Ian M. Sims

  DOI：10.1016/j.bmc.2009.05.043

  日期：2009.7

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.