1,2-di-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose | 374078-96-3

• 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: 1,2-di-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-5,6-diacetyloxy-3,4-dibenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 374078-96-3
• 化学式: C₃₁H₂₈O₁₁
• 分子量: 576.557
• InChiKey: CWZNIWDGPGFSCE-MKOCCIKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose 在 甲醇 、 三氟化硼乙醚 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 phenyl 3,4,6-tri-O-benzoyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Convergent Synthesis of Homogeneous Glc₁Man₉GlcNAc₂-Protein and Derivatives as Ligands of Molecular Chaperones in Protein Quality Control

  摘要：

  A detailed understanding of the molecular mechanism of chaperone-assisted protein quality control is often hampered by the lack of well-defined homogeneous glycoprotein probes. We describe here a highly convergent chemoenzymatic synthesis of the monoglucosylated glycoforms of bovine ribonuclease (RNase) as specific ligands of lectin-like chaperones calnexin (CNX) and calreticulin (CRT) that are known to recognize the monoglucosylated high-mannose oligosaccharide component of glycoproteins in protein folding. The synthesis of a selectively modified glycoform Gal(1)Glc(1)Man(9)GlcNAc(2)-RNase was accomplished by chemical synthesis of a large N-glycan oxazoline and its subsequent enzymatic ligation to GlcNAc-RNase under the catalysis of a glycosynthase. Selective removal of the terminal galactose by a beta-galactosidase gave the Glc(1)Man(9)GlcNAc(2)-RNase glycoform in excellent yield. CD spectroscopic analysis and RNA-hydrolyzing assay indicated that the synthetic RNase glycoforms maintained essentially the same global conformations and were fully active as the natural bovine ribonudease B. SPR binding studies revealed that the Glc(1)Man(9)GlcNAc(2)-RNase had high affinity to lectin CRT, while the synthetic Man(9)GlcNAc(2)-RNase glycoform and natural RNase B did not show CRT-binding activity. These results confirmed the essential role of the glucose moiety in the chaperone molecular recognition. Interestingly, the galactose-masked glycoform Gal(1)Glc(1)Man(9)GlcNAc(2)-RNase also showed significant affinity to lectin CRT, suggesting that a galactose beta-1,4-linked to the key glucose moiety does not significantly block the lectin binding. These synthetic homogeneous glycoprotein probes should be valuable for a detailed mechanistic study on how molecular chaperones work in concert to distinguish between misfolded and folded glycoproteins in the protein quality control cycle.

  DOI：

  10.1021/ja204831z
• 作为产物：
  描述：

  乙酸酐 、 3,4,6-tri-O-benzoyl-D-mannopyranose 以 吡啶 为溶剂， 反应 4.0h， 以100%的产率得到1,2-di-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose
  参考文献：
  名称：

  SYNTHESIS OF A MANNOTETRAOSE—THE REPEATING UNIT OF THE CELL-WALL MANNANS OF MICROSPORUM GYPSEUM AND RELATED SPECIES OF TRYCHOPHYTON

  摘要：

  A tetrasaccharide, alpha -D-mannopyranosyl-(1 -->2)-alpha -D-mannopyranosyl-(1 -->6)-alpha -D-mannopyranosyl-(1 -->6)-D-maanopyranose (1), the repeating unit of the cell-wall mannans of Microsporum gypseum and related species of Trychophyton, was synthesized using 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha -D-mannopyranosyl trichloroacetimidate (5) and 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha -D-mannopyranosyl trichloroacetimidate (13) as the glycosyl donors in "the inverse Schmidt 'procedure.

  DOI：

  10.1081/car-100104864

文献信息

• Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan
  作者：Benjamin Cao、Jonathan M White、Spencer J Williams

  DOI：10.3762/bjoc.7.47

  日期：——

  with host cells. We report the efficient synthesis of a series of azidooctyl di- and trimannosides possessing the following glycan structures: alpha-Man-1,6-alpha-Man, alpha-Man-1,6-alpha-Man-1,6-alpha-Man, alpha-Man-1,2-alpha-Man-1,6-alpha-Man and 2,6-di-(alpha-Man)-alpha-Man. The synthesis includes the use of non-benzyl protecting groups compatible with the azido group and preparation of the branched

  结核分枝杆菌是结核病 (TB) 的病原体，具有复杂的细胞壁，细胞壁含有富含甘露糖的糖磷脂，称为磷脂酰肌醇甘露糖苷 (PIM)、脂甘露聚糖 (LM) 和脂阿拉伯甘露聚糖 (LAM)。这些糖磷脂在细胞壁功能和宿主-病原体相互作用中起重要作用。合成 PIM/LM/LAM 子结构是描绘和剖析甘露糖糖磷脂生物合成及其与宿主细胞相互作用的精细细节的有用生化工具。我们报告了一系列具有以下聚糖结构的叠氮辛基二和三甘露糖苷的有效合成：alpha-Man-1,6-alpha-Man、alpha-Man-1,6-alpha-Man-1,6-alpha-人，alpha-Man-1,2-alpha-Man-1,6-alpha-Man 和 2,6-di-(alpha-Man)-alpha-Man。该合成包括使用与叠氮基相容的非苄基保护基团，以及通过 3,4-丁二缩醛的双糖基化制备支链三糖结构 2,6-二-(α-Man
• Synthesis of a derivative of a pentasaccharide repeating unit of the O-antigenic polysaccharide of the bacterium Klebsiella pneumoniae O3 as a benzoylated 2-methoxycarbonylethyl thioglycoside
  作者：P. I. Abronina、K. I. Galkin、L. V. Backinowsky、A. A. Grachev

  DOI：10.1007/s11172-010-0033-3

  日期：2009.2

  Block synthesis of a fully benzoylated derivative of the pentasaccharide α-d-Manp-(1→3)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-SCH2CH2CO2Me, the glycoside of the repeating unit of the O-antigenic polysaccharide of the bacterium Klebsiella pneumoniae O3, was performed.

  合成一种完全苯甲酰化的五糖衍生物α-d-Manp-(1→3)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-SCH2CH2CO2Me，该衍生物是细菌肺炎克雷伯菌O3型O抗原多糖重复单元的糖苷。
• 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）。
• An Improved Synthetic Route to the Potent Angiogenesis Inhibitor Benzyl Manα(1→3)-Manα(1→3)-Manα(1→3)-Manα(1→2)-Man Hexadecasulfate
  作者：Ligong Liu、Ken D. Johnstone、Jon K. Fairweather、Keith Dredge、Vito Ferro

  DOI：10.1071/ch09015

  日期：——

  An improved synthetic route to α(1→3)/α(1→2)-linked mannooligosaccharides has been developed and applied to a more efficient preparation of the potent anti-angiogenic sulfated pentasaccharide, benzyl Manα(1→3)-Manα(1→3)-Manα(1→3)-Manα(1→2)-Man hexadecasulfate, using only two monosaccharide building blocks. Of particular note are improvements in the preparation of both building blocks and a simpler, final deprotection strategy. The route also provides common intermediates for the introduction of aglycones other than benzyl, either at the building block stage or after oligosaccharide assembly. The anti-angiogenic activity of the synthesized target compound was confirmed via the rat aortic assay.

  我们开发出了α(1→3)/α(1→2)-连接甘露寡糖的改良合成路线，并将其应用于更高效地制备强效抗血管生成硫酸化五糖--苄基 Manα(1→3)-Manα(1→3)-Manα(1→3)-Manα(1→2)-Man 十六碳硫酸酯，只需使用两种单糖结构单元。特别值得注意的是，该方法改进了两种构筑基块的制备，并采用了更简单的最终脱保护策略。该路线还提供了在构建模块阶段或在寡糖组装后引入除苄基以外的苷元的通用中间体。合成的目标化合物的抗血管生成活性已通过大鼠主动脉试验得到证实。
• Synthesis of mannopyranose disaccharides as photoaffinity probes for mannosyltransferases in Mycobacterium tuberculosis
  作者：Ashish K Pathak、Vibha Pathak、James M Riordan、Sudagar S Gurcha、Gurdyal S Besra、Robert C Reynolds

  DOI：10.1016/j.carres.2003.10.031

  日期：2004.2

  play a crucial role in mycobacterial cell-wall biosynthesis and are potential new drug targets for the treatment of tuberculosis. Herein, we describe the synthesis of alpha-(1-->2)- and alpha-(1-->6)-linked mannopyranosyl disaccharides possessing a 5-azidonaphthlene-1-sulfonamidoethyl group as photoaffinity probes for active-site labeling studies of mannosyltransferases in Mycobacterium tuberculosis.

  甘露糖基转移酶在分枝杆菌细胞壁生物合成中起关键作用，并且是治疗结核病的潜在新药靶标。在本文中，我们描述了具有5-azidonaphthlene-1-sulfonamidoethyl基的α-（1-> 2）-和alpha-（1-> 6）-连接的甘露吡喃糖基二糖的合成，作为用于活性位点标记研究的光亲和探针结核分枝杆菌中的甘露糖基转移酶的检测