2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-β-D-mannopyranose | 850883-18-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-β-D-mannopyranose
• 英文别名: Man2Ac3Ac4Ac6Ac(a1-3)b-Man1Ac2Ac4Ac6Ac；[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[(2S,3S,4S,5R,6R)-2,3,5-triacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 850883-18-0
• 化学式: C₂₈H₃₈O₁₉
• 分子量: 678.598
• InChiKey: KXQUPCAOOLXBPP-DOVVIOQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-β-D-mannopyranose 在 偶氮二异丁腈 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 74.0h， 生成 acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose

  摘要：

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.090
• 作为产物：
  描述：

  1,2-O-ethylidene-(R,S)-β-D-mannopyranose 在 4 A molecular sieve 、 sodium acetate 、 silver trifluoromethanesulfonate 、 (+)-10-camphorsulfonic acid 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.67h， 生成 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-β-D-mannopyranose
  参考文献：
  名称：

  Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose

  摘要：

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.090

文献信息

• Structural and Kinetic Dissection of the<i>endo</i>-α-1,2-Mannanase Activity of Bacterial GH99 Glycoside Hydrolases from<i>Bacteroides</i> spp.
  作者：Zalihe Hakki、Andrew J. Thompson、Stephanie Bellmaine、Gaetano Speciale、Gideon J. Davies、Spencer J. Williams

  DOI：10.1002/chem.201405539

  日期：2015.1.26

  Glycoside hydrolase family 99 (GH99) was created to categorize sequence‐related glycosidases possessing endo‐α‐mannosidase activity: the cleavage of mannosidic linkages within eukaryotic N‐glycan precursors (Glc1–3Man9GlcNAc2), releasing mono‐, di‐ and triglucosylated‐mannose (Glc1–3‐1,3‐Man). GH99 family members have recently been implicated in the ability of Bacteroides spp., present within the gut

  糖苷水解酶家族99（GH99）的创建是为了对具有内切α-甘露糖苷酶活性的序列相关糖苷酶进行分类：真核N-聚糖前体（Glc 1-3 Man 9 GlcNAc 2）中甘露糖苷键的裂解，释放单，双-和triglucosylated甘露糖（GLC 1-3 -1,3-曼）。GH99家族成员最近与拟杆菌的能力有关 spp.spp。，存在于肠道菌群内，通过分解分支内的αMan-1,3-αMan→1,2-αMan-1,2-αMan序列来代谢真菌细胞壁α-甘露聚糖，从而释放α-1,3-甘露二糖偏离主要的α-1,6-甘露聚糖骨架。我们报告了一系列底物和抑制剂的开发，我们将其用于在动力学和结构上表征细菌拟南芥（Theactotaides thetaiotaomicron）和xylanisolvens的细菌GH99酶的这种新型内-α-1,2-甘露聚糖酶活性。这些数据表明大约为5 kJ mol -1对-2子位点中相
• Contribution of Shape and Charge to the Inhibition of a Family GH99 <i>endo</i>-α-1,2-Mannanase
  作者：Marija Petricevic、Lukasz F. Sobala、Pearl Z. Fernandes、Lluís Raich、Andrew J. Thompson、Ganeko Bernardo-Seisdedos、Oscar Millet、Sha Zhu、Matthieu Sollogoub、Jesús Jiménez-Barbero、Carme Rovira、Gideon J. Davies、Spencer J. Williams

  DOI：10.1021/jacs.6b10075

  日期：2017.1.25

  Inhibitor design incorporating features of the reaction coordinate and transition-state structure has emerged as a powerful approach for the development of enzyme inhibitors. Such inhibitors find use as mechanistic probes, chemical biology tools, and therapeutics. Endo-α-1,2-mannosidases and endo-α-1,2-mannanases, members of glycoside hydrolase family 99 (GH99), are interesting targets for inhibitor

  结合反应坐标和过渡态结构特征的抑制剂设计已成为开发酶抑制剂的有力方法。此类抑制剂可用作机械探针、化学生物学工具和治疗剂。糖苷水解酶家族 99 (GH99) 的成员内切-α-1,2-甘露糖苷酶和内切-α-1,2-甘露聚糖酶是抑制剂开发的有趣靶标，因为它们在 N-聚糖成熟和微生物酵母甘露聚糖中发挥关键作用降解，分别。建议这些酶通过 1,2-脱水糖“环氧化物”机制发挥作用，该机制通过不寻常的构象路线进行。在这里，我们探讨了形状和电荷如何有助于这些酶的多种抑制剂的结合。我们报告了中性双脱氧、葡糖和环己烯二糖抑制剂的合成，它们与 GH99 内切-α-1,2-甘露聚糖酶的结合，以及通过 X 射线晶体学分析它们的结构。自由能景观的量子力学计算揭示了中性抑制剂如何提供形状而不是所提出的中间和过渡态结构的电荷模拟。基于形状和电荷对抑制家族 GH99 酶的贡献的知识，我们设计并合成了 α-Man-1,3-no