甘露糖磷酸酯 | 40436-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甘露糖磷酸酯
• 英文名称: β-D-mannose 6-phosphate
• 英文别名: mannose 6-phosphate；mannose-6-phosphate；β-D-mannopyranose-6P；O⁶-phosphono-D-mannose；O⁶-phosphono-β-D-mannopyranose；β-D-Mannose-6-phosphat；beta-D-mannose 6-phosphate；[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 40436-61-1
• 化学式: C₆H₁₃O₉P
• 分子量: 260.138
• InChiKey: NBSCHQHZLSJFNQ-RWOPYEJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  D-甘露糖 在 吡啶 、 水 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 25.5h， 生成 甘露糖磷酸酯
  参考文献：
  名称：

  Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates

  摘要：

  The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha-D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-alpha-D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha-D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethylsiyl)-alpha-D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha-D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha-D-glucopyranoside 6-phosphate disodium salt.Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol.Butyl and hexadecyl alpha-D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide in silver triflate-promoted reactions.

  DOI：

  10.1016/0008-6215(92)80082-c

文献信息

• Characterization of a thermotolerant ROK-type mannofructokinase from Streptococcus mitis: application to the synthesis of phosphorylated sugars
  作者：Carine Vergne-Vaxelaire、Aline Mariage、Jean-Louis Petit、Aurélie Fossey-Jouenne、Christine Guérard-Hélaine、Ekaterina Darii、Adrien Debard、Stessy Nepert、Virginie Pellouin、Marielle Lemaire、Anne Zaparucha、Marcel Salanoubat、Véronique de Berardinis

  DOI：10.1007/s00253-018-9018-1

  日期：2018.7

  As proof of concept, 8 hexoses were phosphorylated in moderate to good yields, some of them described for the first time like L-sorbose-5-phosphate unusually phosphorylated in position 5. Its thermotolerance, its wide pH tolerance (from 7 to 10), and temperature range (> 85% activity between 40 and 70 °C) open the way to applications in the enzymatic synthesis of monophosphorylated hexoses.

  迄今为止，大多数已经表征且表现出激酶活性的“阻遏物，开放阅读框，激酶”（ROK）蛋白都以D-葡萄糖为底物。通过探索测序的细菌多样性，已鉴定出61个属于ROK家族的ATP依赖性激酶，并通过实验测定了其己糖的磷酸化程度。主要发现这些激酶是耐热的，并且对D-甘露糖和D-果糖具有高活性，对D-塔格糖具有显着的活性。其中，对中嗜性链球菌的炎症（称为ScrKmitis）的ATP依赖性激酶进行了生物化学表征，并对其底物谱进行了进一步研究。该酶对D-甘露糖和D-果糖的催化效率分别为1.5 106 s-1 M-1和2.7 105 s-1 M-1。但对D-塔格糖（3.5 102 s-1 M-1）和非天然单糖D-altrose（1.1 104 s-1 M-1）和D-塔洛糖（3.4 102 s-1 M-1）也是重要的。对所有己糖测得的比活度显示出对D系列优于L系列的立体偏好。作为概念证明，8己糖以中等到良好的产率
• J. Org. Chem. 1982, 47, 3765-3766
  作者：

  DOI：——

  日期：——
• [EN] USE OF MODIFIED BANANA LECTIN IN PURIFICATION OF GLYCOPROTEINS<br/>[FR] UTILISATION D'UNE LECTINE MODIFIÉE DE LA BANANE DANS LA PURIFICATION DE GLYCOPROTÉINES
  申请人：UNIV MICHIGAN

  公开号：WO2015171975A1

  公开（公告）日：2015-11-12

  The present invention relates to non-naturally occurring or engineered banana lectins, for the purification of glycoproteins which may be advantageous for therapeutic, prophylactic, veterinary or vaccine production for humans or animals.
• Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates
  作者：Morten Meldal、Mette Knak Christensen、Klaus Bock

  DOI：10.1016/0008-6215(92)80082-c

  日期：1992.11

  The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha-D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-alpha-D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha-D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethylsiyl)-alpha-D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha-D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha-D-glucopyranoside 6-phosphate disodium salt.Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol.Butyl and hexadecyl alpha-D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide in silver triflate-promoted reactions.