2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannopyranose | 76375-61-6

• 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-D-mannopyranose
• 英文别名: Ac4ManNAc；2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose；[(2R,3S,4R,5S)-5-acetamido-3,4,6-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 76375-61-6
• 化学式: C₁₆H₂₃NO₁₀
• 分子量: 389.359
• InChiKey: OVPIZHVSWNOZMN-KJAHXBPPSA-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

反应信息

• 作为反应物：
  描述：

  2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannopyranose 在 吡啶 、 sodium azide 、 三氟化硼乙醚 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 sodium iodide 、 palladium dichloride 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 39.58h， 生成 2-acetamido-6-azido-2,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Overproduction of CMP-sialic acid synthetase for organic synthesis

  摘要：

  The gene coding for Escherichia coli CMP-sialic acid synthetase (E.C. 2.7.7.43) was cloned and overexpressed in E. coli through a primer-directed polymerase chain reaction. Two plasmids were constructed to produce the native enzyme and a modified enzyme fused with a decapeptide at the C-terminus. The decapeptide tag was used for detection of the enzyme production. Both enzymes produced from E. coli were isolated and purified with an Orange A dye resin and FPLC. Their properties were compared with respect to their kinetic parameters, stability, pH profiles, and substrate specificities. Both enzymes have similar k(cat) and K(m) for NeuAc and CTP but different pH profiles. Contrary to the native enzyme, the modified enzyme is more active at higher pH. Studies on specificity indicate that both enzymes have a high specific activity for C-9 modified NeuAc derivatives at neutral pH. Some C-5 modified (hydroxy, deoxy, and deoxyfluoro) NeuAc derivatives are not acceptable as substrates. The modified enzyme has been used in the synthesis of CMP-NeuAc from ManNAc and CMP and sialyl N-acetyllactosamine (Neu-alpha-2,6Gal-beta-1,4GlcNAc) with in situ generation of NeuAc and regeneration of CMP-NeuAc. The 6-O-acyl derivatives of ManNAc were prepared via transesterification in anhydrous dimethylformamide by using an engineered stable subtilisin variant as a catalyst, and the products were used as substrates in sialic acid aldolase-catalyzed synthesis of 9-O-acyl-NeuAc derivatives.

  DOI：

  10.1021/ja00036a044
• 作为产物：
  描述：

  N-acetyl-D-mannosamine 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以90%的产率得到2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannopyranose
  参考文献：
  名称：

  Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline

  摘要：

  描述了一种大规模制备o-和p-硝基苯基2-乙酰氨基-2-脱氧-α-D-甘露糖苷的合成方法。该合成途径采用苯酚与ManNAc oxazoline的糖基化，然后通过芳香基的硝化产生可分离的o-和p-硝基苯基衍生物混合物，比例为2:3。

  DOI：

  10.3762/bjoc.8.48

文献信息

• [EN] HYBRID SCFA-HYDROXYL-DERIVATIZED MONOSACCHARIDES, METHODS OF SYNTHESIS, AND METHODS OF TREATING DISORDERS<br/>[FR] MONOSACCHARIDES HYBRIDES DÉRIVATISÉS AVEC HYDROXYLE /SCFA (ACIDES GRAS À CHAÎNE COURTE), PROCÉDÉS DE SYNTHÈSE, ET PROCÉDÉS DE TRAITEMENT DE TROUBLES
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2009020641A1

  公开（公告）日：2009-02-12

  Described herein are fatty acid carbohydrate-hydroxyl-hybrid compounds and derivatives thereof, and methods of treating or preventing disease and disease symptoms using the compounds and compositions thereof.

  本文描述了脂肪酸碳水化合物及其衍生物，以及利用这些化合物及其组合物治疗或预防疾病和疾病症状的方法。
• Carbohydrate–Neuroactive Hybrid Strategy for Metabolic Glycan Engineering of the Central Nervous System <i>in Vivo</i>
  作者：Asif Shajahan、Shubham Parashar、Surbhi Goswami、Syed Meheboob Ahmed、Perumal Nagarajan、Srinivasa-Gopalan Sampathkumar

  DOI：10.1021/jacs.6b08894

  日期：2017.1.18

  carbohydrate-neuroactive hybrid (CNH) molecules, which exploit carrier-mediated transport systems available at the blood-brain barrier, to access brain via tail vein injection in mice. Peracetylated N-azidoacetyl-d-mannosamine (Ac4ManNAz) conjugated with neuroactive carriers, namely, nicotinic acid, valproic acid, theophylline-7-acetic acid, and choline, were synthesized and evaluated in SH-SY5Y (human neuroblastoma)

  唾液酸在中枢神经系统 (CNS) 中含量丰富，对大脑发育、学习和记忆至关重要。已知唾液酸-糖复合物生物合成的失调与神经系统疾病、中枢神经系统损伤和脑癌有关。代谢聚糖工程 (MGE) 和生物正交连接使研究聚糖在体内的生物学作用成为可能；然而，对大脑中唾液酸聚糖的直接研究一直是棘手的。我们报告了一种利用碳水化合物-神经活性杂化 (CNH) 分子的简单策略，该策略利用血脑屏障中可用的载体介导的运输系统，通过小鼠尾静脉注射进入大脑。与神经活性载体（即烟酸、丙戊酸、茶碱-7-乙酸和胆碱）结合的全乙酰化 N-叠氮基乙酰基-d-甘露糖胺 (Ac4ManNAz)，在 SH-SY5Y（人神经母细胞瘤）细胞中合成并评估 MGE。在小鼠（C57BL/6J 和 BALB/cByJ）中静脉注射 CNH 分子导致大脑和心脏中携带 N-叠氮基乙酰神经氨酸 (NeuAz) 的糖蛋白的强烈表达，而非杂交分子 Ac4ManNAz
• Protein S-Glyco-Modification through an Elimination–Addition Mechanism
  作者：Ke Qin、Hao Zhang、Zhenqi Zhao、Xing Chen

  DOI：10.1021/jacs.0c02110

  日期：2020.5.20

  S-glyco-modification. In alkaline protein microenvironments, per-O-acetylated monosaccharides undergo base-promoted β-elimination to form thiol-reactive α,β-unsaturated aldehydes, which then react with cysteine residues via Michael addition. This S-glyco-modification produces 3-thiolated sugars in the hemiacetal form, rather than typical glycosides. The elimination-addition mechanism guides us to develop

  含有生物正交基团的全-O-乙酰化非天然单糖已被广泛用于活细胞中的代谢聚糖标记 (MGL) 二十年，但直到最近我们才发现蛋白质半胱氨酸之间存在人工“S-糖基化”和过氧乙酰化糖。虽然正在努力避免 MGL 中的这种非特异性反应，但反应机制仍然未知。在这里，我们提出了一项详细的机制研究，揭示了一种称为蛋白质 S-糖修饰的非典型糖基化。在碱性蛋白质微环境中，过氧乙酰化单糖经过碱促进的 β-消除形成硫醇反应性 α,β-不饱和醛，然后通过迈克尔加成与半胱氨酸残基反应。这种 S-糖基修饰产生半缩醛形式的 3-硫醇化糖，而不是典型的糖苷。消除加成机制指导我们开发 1,6-二-O-丙酰化 N-叠氮基乙酰半乳糖胺 (1,6-Pr2GalNAz) 作为改进的 MGL 非天然单糖。
• Glycan-Specific Metabolic Oligosaccharide Engineering of C7-Substituted Sialic Acids
  作者：Heinz Möller、Verena Böhrsch、Joachim Bentrop、Judith Bender、Stephan Hinderlich、Christian P. R. Hackenberger

  DOI：10.1002/anie.201108809

  日期：2012.6.11

  A new sialic acid in the house! A biosynthetic approach gives access to previously inaccessible C7 modifications of sialic acids in living cells. Metabolic incorporation of synthetically derived N‐acetyl‐4‐azido‐4‐deoxymannosamine (see scheme) into glycans of mammalian cells and zebrafish larvae preserves the bioorthogonal functionality of its azido group for subsequent labeling with biophysical probes

  房子里有一种新的唾液酸！生物合成方法使人们能够在活细胞中获得唾液酸以前无法接近的C7修饰。将合成衍生的N-乙酰基-4-叠氮基-4-脱氧甘露糖胺（见方案）代谢掺入哺乳动物细胞和斑马鱼幼虫的聚糖中，保留了其叠氮基团的生物正交功能，可随后用生物物理探针标记。
• Modified GM3 gangliosides produced by metabolic oligosaccharide engineering
  作者：Chad M. Whitman、Fan Yang、Jennifer J. Kohler

  DOI：10.1016/j.bmcl.2011.04.128

  日期：2011.9

  Metabolic oligosaccharide engineering is powerful approach to altering the structure of cellular sialosides. This method relies on culturing cells with N-acetylmannosamine (ManNAc) analogs that are metabolized to their sialic acid counterparts and added to glycoproteins and glycolipids. Here we employed two cell lines that are deficient in ManNAc biosynthesis and examined their relative abilities to

  代谢寡糖工程是改变细胞唾液酸苷结构的有效方法。这种方法依赖于用N培养细胞-乙酰甘露糖胺 (ManNAc) 类似物被代谢为唾液酸对应物并添加到糖蛋白和糖脂中。在这里，我们采用了两种缺乏 ManNAc 生物合成的细胞系，并检查了它们将一组 ManNAc 类似物代谢为唾液酸苷的相对能力。除了测量全球唾液酸苷产量，我们还检测了含唾液酸的糖脂 GM3 的生物合成。我们发现这两种细胞系在区分 ManNAc 变体形式的能力方面存在差异。此外，我们的数据表明，唾液酸的修饰形式可能优先纳入某些唾液酸苷，而从其他唾液酸中排除。总之，我们的结果表明对唾液酸生产的全局分析可以掩盖唾液酸特异性差异。