D-mannopyranose 6-phosphate | 723729-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-mannopyranose 6-phosphate
• 英文别名: mannose 6-phosphate；D-mannose-6-phosphate；M6P；Mannose-6-phosphate；[(2R,3S,4S,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 723729-16-6
• 化学式: C₆H₁₃O₉P
• 分子量: 260.138
• InChiKey: NBSCHQHZLSJFNQ-QTVWNMPRSA-N

物化性质

• 沸点：
  564.1±60.0 °C(Predicted)
• 密度：
  1.970±0.06 g/cm3(Predicted)
• 碰撞截面：
  155.8 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

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

• 作为反应物：
  描述：

  D-mannopyranose 6-phosphate 生成 mannose-1-phosphate
  参考文献：
  名称：

  Pallanca, Jane E.; Turner, Nicolas J., Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 3017 - 3022

  摘要：

  DOI：
• 作为产物：
  描述：

  fructose 6-phosphate 在 Thermus thermophilus KCCM 40879 recombinant mannose-6-phosphate isomerase 作用下， 反应 0.08h， 生成 D-mannopyranose 6-phosphate
  参考文献：
  名称：

  Molecular characterization of a novel thermostable mannose-6-phosphate isomerase from Thermus thermophilus

  摘要：

  Mannose-6-phosphate isomerase catalyzes the interconversion of mannose-6-phosphate and fructose-6-phosphate. The gene encoding a putative mannose-6-phosphate isomerase from Thermus thermophilus was cloned and expressed in Escherichia colt. The native enzyme was a 29 kDa monomer with activity maxima for mannose 6-phosphate at pH 7.0 and 80 degrees C in the presence of 0.5 mM Zn(2+) that was present at one molecule per monomer. The half-lives of the enzyme at 65, 70, 75, 80, and 85 degrees C were 13, 6.5, 3.7, 1.8, and 0.2 h, respectively. The 15 putative active-site residues within 4.5 angstrom of the substrate mannose 6-phosphate in the homology model were individually replaced with other amino acids. The sequence alignments, activities, and kinetic analyses of the wild-type and mutant enzymes with amino acid changes at His50, Glu67, His122, and Glu132 as well as homology modeling suggested that these four residues are metal-binding residues and may be indirectly involved in catalysis. In the model, Arg11, Lys37, Gln48, Lys65 and Arg142 were located within 3 angstrom of the bound mannose 6-phosphate. Alanine substitutions of Gln48 as well as Arg142 resulted in increase of K(m) and dramatic decrease of k(cat), and alanine substitutions of Arg11, Lys37, and Lys65 affected enzyme activity. These results suggest that these 5 residues are substrate-binding residues. Although Trp13 was located more than 3 angstrom from the substrate and may not interact directly with substrate or metal, the ring of Trp13 was essential for enzyme activity. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2011.05.040

文献信息

• Regioselective Phosphorylation of Carbohydrates and Various Alcohols by Bacterial Acid Phosphatases; Probing the Substrate Specificity of the Enzyme fromShigella flexneri
  作者：Teunie van Herk、Aloysius F. Hartog、Alida M. van der Burg、Ron Wever

  DOI：10.1002/adsc.200505072

  日期：2005.6

  broad range of carbohydrates and alcohols. Many cyclic carbohydrates are phosphorylated in a regioselective manner. Non-cyclic carbohydrates are phosphorylated as well. Phosphorylation of linear alcohols, cyclic and aromatic alcohols is also possible. In all cases the acid phosphatase from Shigella prefers a primary alcohol function above a secondary one. We conclude that these enzymes are an attractive

  细菌非特异性酸性磷酸酶通常催化多种底物的去磷酸化。如前所述，来自弗氏志贺氏菌和肠炎沙门氏菌的酶也能够使用廉价的焦磷酸盐作为磷酸盐供体，催化将肌苷磷酸化为肌苷单磷酸和将D-葡萄糖磷酸化为D-葡萄糖6-磷酸（D-G6P）。经过优化后，在后一反应中可实现高收率（95％），我们在此表明​​可以以制备方式使用这些酶。这促使我们使用31P NMR和HPLC还可以使多种碳水化合物和醇类进行磷酸化。许多环状碳水化合物以区域选择性方式被磷酸化。非环状碳水化合物也被磷酸化。直链醇，环状和芳族醇的磷酸化也是可能的。在所有情况下，志贺氏菌的酸性磷酸酶都比伯醇更喜欢伯醇功能。我们得出结论，在广泛范围的化合物磷酸化中，这些酶是现有化学和酶促方法的一种有吸引力的替代物。
• Molecular recognition in the P2Y14 receptor: Probing the structurally permissive terminal sugar moiety of uridine-5′-diphosphoglucose
  作者：Hyojin Ko、Arijit Das、Rhonda L. Carter、Ingrid P. Fricks、Yixing Zhou、Andrei A. Ivanov、Artem Melman、Bhalchandra V. Joshi、Pavol Kováč、Jan Hajduch、Kenneth L. Kirk、T. Kendall Harden、Kenneth A. Jacobson

  DOI：10.1016/j.bmc.2009.05.024

  日期：2009.7

  substitution by chain extension through an amide linkage. Functionalized congeners containing terminal 2-acylaminoethylamides prepared by this strategy retained P2Y14 activity, and molecular modeling predicted close proximity of this chain to the second extracellular loop of the receptor. In addition, replacement of glucose with other sugars did not diminish P2Y14 potency. For example, the [5′′]ribose derivative

  P2Y 14受体是一种核苷酸信号蛋白，由尿苷-5'-二磷酸葡萄糖1和其他尿嘧啶核苷酸激活。我们已经确定1的葡萄糖部分是设计该 P2Y 14激动剂类似物的最结构允许区域。例如，尿苷-5'-二磷酸葡萄糖醛酸的羧酸酯基团被证明适用于通过酰胺键进行链延伸的灵活取代。通过该策略制备的含有末端 2-酰基氨基乙基酰胺的功能化同源物保留了 P2Y 14活性，分子模型预测该链与受体的第二个细胞外环非常接近。此外，用其他糖替代葡萄糖不会降低 P2Y 14效力。例如，[5'']核糖衍生物的EC 50为0.24 μM。的葡萄糖部分的选择性monofluorination指示用于2'角色' -和6'' -的羟基1受体识别。β-葡萄糖苷的效力比天然 α-异构体低两倍，但 1''-氧的亚甲基替代消除了活性。用环戊基或刚性双环 [3.1.0] 己烷基团取代核糖环系统消除了活性。Uridine-5'-diphosphoglucose
• Biochemical characterization of a recombinant acid phosphatase from Acinetobacter baumannii
  作者：Elizabeth Smiley-Moreno、Douglas Smith、Jieh-Juen Yu、Phuong Cao、Bernard P. Arulanandam、James P. Chambers

  DOI：10.1371/journal.pone.0252377

  日期：——

  variety of reagents, i.e., detergents, reducing, and chelating agents as well as classic acid phosphatase inhibitors was examined in addition to assessment of hydrolysis of a number of phosphorylated compounds. Removal of phosphate from different phosphorylated compounds is supportive of broad, i.e., 'nonspecific' substrate specificity; although, the enzyme appears to prefer phosphotyrosine and/or peptides

  鲍曼不动杆菌的基因组序列分析显示存在推定的酸性磷酸酶 (AcpA；EC 3.1.3.2)。制备质粒构建体，并在大肠杆菌中表达重组蛋白 (rAcpA)。镍亲和纯化蛋白的 PAGE 分析（在变性/还原条件下进行）显示存在大约 37 kDa 的近均质条带。37 kDa 物种的身份通过蛋白质组学分析证实为 rAcpA，其分子量为 34.6 kDa，来自推导的序列。底物水解对 pH 值的依赖性很广，观察到的最佳值在 6.0。动力学分析显示对 PNPP (Km = 90 μM) 的亲和力相对较高，Vmax、kcat 和 Kcat/Km 值为 19.2 pmoles s-1、4.80 s-1（基于 37 kDa 计算）和 5.30 x 104 M -1s-1，分别。除了评估许多磷酸化化合物的水解外，还检查了对各种试剂的敏感性，即去污剂、还原剂和螯合剂以及经典的酸性磷酸酶抑制剂。从不同的磷酸化化合物中去除
• A mutant of phosphomannomutase1 retains full enzymatic activity, but is not activated by IMP: Possible implications for the disease PMM2-CDG
  作者：Valentina Citro、Chiara Cimmaruta、Ludovica Liguori、Gaetano Viscido、Maria Vittoria Cubellis、Giuseppina Andreotti

  DOI：10.1371/journal.pone.0189629

  日期：——

  responsible for PMM2-CDG. Although not directly causative of the disease, the role of the paralogous enzyme in the disease should be clarified. Phosphomannomutase1 could have a beneficial effect, contributing to mannose 6-phosphate isomerization, or a detrimental effect, hydrolyzing the bis-phosphate hexose activator. A pivotal role in regulating mannose-1phosphate production and ultimately protein glycosylation

  糖基化最常见的疾病是PMM2-CDG，是由磷酸甘露糖突变酶活性不足引起的。在人类中，存在两种旁系酶，它们都需要甘露糖1,6-双磷酸酯或葡萄糖1,6-双磷酸酯作为激活剂，但只有磷酸甘露糖变酶1水解双磷酸己糖。编码磷酸甘露糖突变酶2的基因中的突变负责PMM2-CDG。尽管不是直接引起疾病的原因，但应阐明同源酶在疾病中的作用。磷酸甘露糖突变酶1可能具有有益的作用，有助于将甘露糖6-磷酸异构化，或者有害的作用是水解双磷酸己糖活化剂。肌苷单磷酸可能会在调节1-磷酸甘露糖的产生和最终蛋白质糖基化中起关键作用，从而增强磷酸甘露糖突变酶1的磷酸酶活性。在本文中，我们通过常规酶法以及31P-NMR和热位移法等新技术分析了人磷酸单核苷酸酶。我们表征了phospomannomutase1的三个突变体，其保留了突变酶和磷酸酶的活性，但无法结合肌苷单磷酸。
• NOVEL USES OF D-MANNOPYRANOSE DERIVATIVES
  申请人：Monteron Jean-Louis

  公开号：US20110112044A1

  公开（公告）日：2011-05-12

  The invention relates to the use of mannose-6-phosphate (M6P) and of certain derivatives thereof for controlling angiogenesis and ligament regeneration and/or cartilage reconstruction. The MP6 and certain derivatives thereof can particularly be used for preparing a pharmaceutical composition used for ligament regeneration and/or cartilage reconstruction.

  该发明涉及利用甘露糖-6-磷酸（M6P）及其某些衍生物来控制血管生成、韧带再生和/或软骨重建。M6P及其某些衍生物特别可用于制备用于韧带再生和/或软骨重建的药物组合物。