2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-mannopyranose | 6730-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-mannopyranose
• 英文别名: 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-mannose；1,3,4,6-Tetra-o-acetyl-2-acetamido-2-deoxy-beta-d-mannose；[(2R,3S,4R,5S,6S)-5-acetamido-3,4,6-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 6730-10-5
• 化学式: C₁₆H₂₃NO₁₀
• 分子量: 389.359
• InChiKey: OVPIZHVSWNOZMN-YIDVYQOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-mannopyranose 在 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 2-acetamido-1,5-anhydro-2-deoxy-D-mannitol
  参考文献：
  名称：

  Identification, Characteristics and Mechanism of 1-Deoxy-N-acetylglucosamine from Deep-Sea Virgibacillus dokdonensis MCCC 1A00493

  摘要：

  引起稻米细菌性斑点病的黄单胞菌（Xanthomonas oryzae pv. oryzae）是最具破坏性的病原菌之一。近年来，针对植物病原菌的生物防治受到了越来越多的关注。1-脱氧-N-乙酰氨基葡萄糖（1-DGlcNAc）是从维尔吉巴克氏菌（Virgibacillus dokdonensis）MCCC 1A00493发酵的上清液中通过抗菌生物活性导向分离提取得到的。其结构通过液相色谱-质谱联用（LC/MS）、核磁共振（NMR）、化学合成和时间相关密度泛函理论（TD-DFT）计算进行了阐明。1-DGlcNAc能够特异性抑制X. oryzae pv. oryzae PXO99A（最低抑制浓度为23.90 μg/mL），但对其他常见病原菌如黄单胞菌（Xanthomonas campestris pv. campestris str.8004）及稻瘟病菌（Xanthomonas oryzae pv. oryzicola RS105）无活性。然而，其一个二旋映体（2-乙酰氨基-1,5-脱水-D-甘露醇）同样对X. oryzae pv. oryzae没有活性。这个结果表明，1-DGlcNAc的活性与2-乙酰氨基基团的空间构象差异有关，这可能归因于它们与受体的不同相互作用。通过blastp分析，发现与8004和RS105菌株基因组相比，X. oryzae pv. oryzae PXO99A中有84种独特蛋白存在。这些独特蛋白可能与1-DGlcNAc之间存在独特的相互作用。定量实时PCR和pharmMapper服务器显示，与细胞分裂相关的蛋白可能是PXO99A中的靶点。本研究表明，活性物质的特异性基于活性基团和空间构象的选择，这些独特蛋白可能有助于揭示1-DGlcNAc对PXO99A的特定作用机制。

  DOI：

  10.3390/md16020052
• 作为产物：
  描述：

  2-acetamido-1,2-dideoxy-1-nitro-D-mannitol 在 sodium hydroxide 作用下， 生成 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-mannopyranose
  参考文献：
  名称：

  AN ASYMMETRIC SYNTHESIS OFD- ANDL-MANNOSAMINE

  摘要：

  对D-arabo-tetraacetoxy-1-nitrohexene-1的乙烯基键加入氨是立体特异性的，并形成了结晶产物1-硝基-1-去氧-N-乙酰-D-甘露氨基醇。将Nef反应应用于这种化合物，得到2-氨基-2-去氧-D-甘露糖，它以结晶五乙酰基盐的形式被分离，并通过用盐酸脱乙酰化来进一步表征为盐酸盐。然而，在用钡甲氧化物脱乙酰化五乙酰基盐时，发生了异常的外消旋反应，产生了N-乙酰-D-葡萄糖胺。类似地，L-arabo-tetra-acetoxy-1-nitrohexene-1也可以合成L-甘露氨基醇五乙酰基盐。

  DOI：

  10.1139/v59-253

文献信息

• [EN] SUGAR-LINKED AMINO ACIDS FOR SOLID-PHASE PEPTIDE SYNTHESIS<br/>[FR] ACIDES AMINÉS LIÉS À DES SUCRES POUR LA SYNTHÈSE DE PEPTIDES EN PHASE SOLIDE
  申请人：UNIV INDIANA RES & TECH CORP

  公开号：WO2019074833A1

  公开（公告）日：2019-04-18

  The present disclosure relates to sugar-linked amino acids and processes for preparing the same. The sugar-linked amino acids may be used for solid-phase peptide synthesis. A sugar compound and an amino acid compound having a nucleophilic side chain are reacted in a heated halogenated solvent. The reaction is catalyst by a Lewis acid, such as InBr3. The reaction is performed as a batch or continuous process.

  本公开涉及与糖连接的氨基酸以及制备这些氨基酸的方法。这些糖连接的氨基酸可用于固相肽合成。在加热的卤代溶剂中，糖化合物和具有亲核侧链的氨基酸化合物发生反应。该反应由Lewis酸（如InBr3）催化。该反应可作为批量或连续过程进行。
• Enzymes in carbohydrate synthesis. Lipase-catalyzed selective acylation and deacylation of furanose and pyranose derivatives
  作者：William J. Hennen、H. Marcel Sweers、Yi Fong Wang、Chi Huey Wong

  DOI：10.1021/jo00256a008

  日期：1988.10
• Comparison of chemical and enzymatic synthesis of 2-acetamido-2-deoxy-d-mannose 6-phosphate: a new approach
  作者：Mei-Zheng Liu、Yuan C. Lee

  DOI：10.1016/s0008-6215(00)00299-8

  日期：2001.2

  Chemical and enzymatic methods to synthesis of 2-acetamido-2-deoxy-D-mannose-6-phosphate (ManNAc-6-P) have been investigated. A new preparative method has been developed although some established procedures were tried. In this new method, a 6-O-acetyl or 4,6-di-O-acetyl group of the per-O-acetylated 2-acetamido-2-deoxy-D-mannose (ManNAc) were regioselectively removed with an esterase from the yellow yeast, Rhonosporidium toruloides, followed by phosphorylation and O-deacetylation under mild conditions. H-1 and C-13 NMR data spectra of ManNAc-6-P were recorded. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Identification, Characteristics and Mechanism of 1-Deoxy-N-acetylglucosamine from Deep-Sea Virgibacillus dokdonensis MCCC 1A00493
  作者：Dian Huang、Zong-Ze Shao、Yi Yu、Min-Min Cai、Long-Yu Zheng、Guang-Yu Li、Zi-Niu Yu、Xian-Feng Yi、Ji-Bin Zhang、Fu-Hua Hao

  DOI：10.3390/md16020052

  日期：——

  Xanthomonas oryzae pv. oryzae, which causes rice bacterial blight, is one of the most destructive pathogenic bacteria. Biological control against plant pathogens has recently received increasing interest. 1-Deoxy-N-acetylglucosamine (1-DGlcNAc) was extracted from the supernatant of Virgibacillus dokdonensis MCCC 1A00493 fermentation through antibacterial bioassay-guided isolation. Its structure was elucidated by LC/MS, NMR, chemical synthesis and time-dependent density functional theory (TD-DFT) calculations. 1-DGlcNAc specifically suppressed X. oryzae pv. oryzae PXO99A (MIC was 23.90 μg/mL), but not other common pathogens including Xanthomonas campestris pv. campestris str.8004 and Xanthomonas oryzae pv. oryzicola RS105. However, its diastereomer (2-acetamido-1,5-anhydro-2-deoxy-d-mannitol) also has no activity to X. oryzae pv. oryzae. This result suggested that activity of 1-DGlcNAc was related to the difference in the spatial conformation of the 2-acetamido moiety, which might be attributed to their different interactions with a receptor. Eighty-four unique proteins were found in X. oryzae pv. oryzae PXO99A compared with the genome of strains8004 and RS105 by blastp. There may be unique interactions between 1-DGlcNAc and one or more of these unique proteins in X. oryzae pv. oryzae. Quantitative real-time PCR and the pharmMapper server indicated that proteins involved in cell division could be the targets in PXO99A. This research suggested that specificity of active substance was based on the active group and spatial conformation selection, and these unique proteins could help to reveal the specific mechanism of action of 1-DGlcNAc against PXO99A.

  引起稻米细菌性斑点病的黄单胞菌（Xanthomonas oryzae pv. oryzae）是最具破坏性的病原菌之一。近年来，针对植物病原菌的生物防治受到了越来越多的关注。1-脱氧-N-乙酰氨基葡萄糖（1-DGlcNAc）是从维尔吉巴克氏菌（Virgibacillus dokdonensis）MCCC 1A00493发酵的上清液中通过抗菌生物活性导向分离提取得到的。其结构通过液相色谱-质谱联用（LC/MS）、核磁共振（NMR）、化学合成和时间相关密度泛函理论（TD-DFT）计算进行了阐明。1-DGlcNAc能够特异性抑制X. oryzae pv. oryzae PXO99A（最低抑制浓度为23.90 μg/mL），但对其他常见病原菌如黄单胞菌（Xanthomonas campestris pv. campestris str.8004）及稻瘟病菌（Xanthomonas oryzae pv. oryzicola RS105）无活性。然而，其一个二旋映体（2-乙酰氨基-1,5-脱水-D-甘露醇）同样对X. oryzae pv. oryzae没有活性。这个结果表明，1-DGlcNAc的活性与2-乙酰氨基基团的空间构象差异有关，这可能归因于它们与受体的不同相互作用。通过blastp分析，发现与8004和RS105菌株基因组相比，X. oryzae pv. oryzae PXO99A中有84种独特蛋白存在。这些独特蛋白可能与1-DGlcNAc之间存在独特的相互作用。定量实时PCR和pharmMapper服务器显示，与细胞分裂相关的蛋白可能是PXO99A中的靶点。本研究表明，活性物质的特异性基于活性基团和空间构象的选择，这些独特蛋白可能有助于揭示1-DGlcNAc对PXO99A的特定作用机制。
• AN ASYMMETRIC SYNTHESIS OF<scp>D</scp>- AND<scp>L</scp>-MANNOSAMINE
  作者：A. N. O'Neill

  DOI：10.1139/v59-253

  日期：1959.10.1

  The addition of ammonia to the ethylenic bond of D-arabo-tetraacetoxy-1-nitrohexene-1 was stereospecific and formed a crystalline product, 1-nitro-1-deoxy-N-acetyl-D-mannosaminol. Application of the Nef reaction to this compound gave 2-amino-2-deoxy-D-mannose, which was isolated as the crystalline pentaacetate and further characterized as the hydrochloride by deacetylation with hydrochloric acid. In the deacetylation of the pentaacetate with barium methoxide, however, an abnormal epimerization occurred to yield N-acetyl-D-glucosamine.L-Mannosamine pentaacetate was synthesized in a similar manner from L-arabo-tetra-acetoxy-1-nitrohexene-1.

  对D-arabo-tetraacetoxy-1-nitrohexene-1的乙烯基键加入氨是立体特异性的，并形成了结晶产物1-硝基-1-去氧-N-乙酰-D-甘露氨基醇。将Nef反应应用于这种化合物，得到2-氨基-2-去氧-D-甘露糖，它以结晶五乙酰基盐的形式被分离，并通过用盐酸脱乙酰化来进一步表征为盐酸盐。然而，在用钡甲氧化物脱乙酰化五乙酰基盐时，发生了异常的外消旋反应，产生了N-乙酰-D-葡萄糖胺。类似地，L-arabo-tetra-acetoxy-1-nitrohexene-1也可以合成L-甘露氨基醇五乙酰基盐。