uridine 5'-diphospho-2-hydroxyacetamido-2-deoxy-α-D-glucopyranoside | 1338332-55-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: uridine 5'-diphospho-2-hydroxyacetamido-2-deoxy-α-D-glucopyranoside
• 英文别名: UDP-N-hydroxyacetylglucosamine
• CAS: 1338332-55-0
• 化学式: C₁₇H₂₇N₃O₁₈P₂
• 分子量: 623.358
• InChiKey: LGOFPGYCBSRKSO-RTSQYROYSA-N

物化性质

• 密度：
  1.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.68
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  326.09
• 氢给体数：
  10.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  uridine 5'-diphospho-2-hydroxyacetamido-2-deoxy-α-D-glucopyranoside 在 recombinant human GalE epimerase 作用下， 生成
  参考文献：
  名称：

  Metabolism of Vertebrate Amino Sugars with N-Glycolyl Groups

  摘要：

  The O-GlcNAc modification involves the attachment of single beta-O-linked N-acetylglucosamine residues to serine and threonine residues of nucleocytoplasmic proteins. Interestingly, previous biochemical and structural studies have shown that O-GlcNAcase (OGA), the enzyme that removes O-GlcNAc from proteins, has an active site pocket that tolerates various N-acyl groups in addition to the N-acetyl group of GlcNAc. The remarkable sequence and structural conservation of residues comprising this pocket suggest functional importance. We hypothesized this pocket enables processing of metabolic variants of O-GlcNAc that could be formed due to inaccuracy within the metabolic machinery of the hexosamine biosynthetic pathway. In the accompanying paper (Bergfeld, A. K., Pearce, O. M., Diaz, S. L., Pham, T., and Varki, A. (2012) J. Biol. Chem. 287, 28865-28881), N-glycolylglucosamine (GlcNGc) was shown to be a catabolite of NeuNGc. Here, we show that the hexosamine salvage pathway can convert GlcNGc to UDP-GlcNGc, which is then used to modify proteins with O-GlcNGc. The kinetics of incorporation and removal of O-GlcNGc in cells occur in a dynamic manner on a time frame similar to that of O-GlcNAc. Enzymatic activity of O-GlcNAcase (OGA) toward a GlcNGc glycoside reveals OGA can process glycolyl-containing substrates fairly efficiently. A bacterial homolog (BtGH84) of OGA, from a human gut symbiont, also processes O-GlcNGc substrates, and the structure of this enzyme bound to a GlcNGc-derived species reveals the molecular basis for tolerance and binding of GlcNGc. Together, these results demonstrate that analogs of GlcNAc, such as GlcNGc, are metabolically viable species and that the conserved active site pocket of OGA likely evolved to enable processing of mis-incorporated analogs of O-GlcNAc and thereby prevent their accumulation. Such plasticity in carbohydrate processing enzymes may be a general feature arising from inaccuracy in hexosamine metabolic pathways.

  DOI：

  10.1074/jbc.m112.363721
• 作为产物：
  描述：

  尿苷-5'-三磷酸 在 甲醇 、 inorganic pyrophosphatase cloned from Pasteurella multocida strain P-1059 、 N-acetylglucosamine-1-phosphate uridylyltransferase cloned from Pasteurella multocida strain P-1059 (ATCC₁₅₇₄₂) 、 N-acetylhexosamine 1-kinase cloned from Bifidobacterium longum ATCC₅₅₈₁₃ 、 水 、 sodium methylate 、 碳酸氢钠 、 potassium carbonate 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 uridine 5'-diphospho-2-hydroxyacetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  One-pot three-enzyme synthesis of UDP-GlcNAc derivatives

  摘要：

  一种荚膜多糖杆菌N-乙酰葡糖胺1-磷酸尿苷酰转移酶（PmGlmU）被克隆并有效用于与N-乙酰己糖胺1-激酶（NahK_ATCC55813）及无机焦磷酸酶（PmPpA）联合，实现了一锅法三酶合成UDP-GlcNAc衍生物，必要时可进一步进行化学衍生化。

  DOI：

  10.1039/c1cc14034e

文献信息

• Donor substrate promiscuity of bacterial β1–3-N-acetylglucosaminyltransferases and acceptor substrate flexibility of β1–4-galactosyltransferases
  作者：Yanhong Li、Mengyang Xue、Xue Sheng、Hai Yu、Jie Zeng、Vireak Thon、Yi Chen、Musleh M. Muthana、Peng G. Wang、Xi Chen

  DOI：10.1016/j.bmc.2016.02.043

  日期：2016.4

  beta4GalTs, donor substrate specificity studies of two bacterial beta3GlcNAcTs from Helicobacter pylori (Hpbeta3GlcNAcT) and Neisseria meningitidis (NmLgtA), respectively, using a library of 39 sugar nucleotides were carried out. The two beta3GlcNAcTs have complementary donor substrate promiscuity and 13 different trisaccharides were produced. They were used to investigate the acceptor substrate specificities

  beta1-3-N-乙酰氨基葡萄糖氨基转移酶（beta3GlcNAcTs）和beta1-4-半乳糖基转移酶（beta4GalTs）已广泛用于酶法合成含N-乙酰乳糖胺（LacNAc）的寡糖和包括聚LacNAc和乳糖（N-新四糖）的糖缀合物LNnT）存在于人类和其他哺乳动物的乳汁中。为了探索可以通过β3GlcNAcT和β4GalT的组合合成的寡糖和衍生物，分别使用39个糖核苷酸库对来自幽门螺杆菌（Hpbeta3GlcNAcT）和脑膜炎奈瑟氏球菌（NmLgtA）的两种细菌β3GlcNAcT的供体底物特异性进行了研究。执行。这两个beta3GlcNAcT具有互补的供体底物混杂，并产生了13种不同的三糖。他们分别用来研究三种脑膜炎奈瑟氏球菌（NmLgtB），幽门螺杆菌（Hpbeta4GalT）和牛（Bbeta4GalT）的beta4GalT的受体底物特异性。13种三糖中有10种被证明是这些beta4
• CHEMOENZYMATIC SYNTHESIS OF HEPARIN AND HEPARAN SULFATE ANALOGS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20140235575A1

  公开（公告）日：2014-08-21

  The present invention provides a one-pot multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.

  本发明提供了一种一锅多酶法，用于从简单糖起始材料制备UDP糖。该发明还提供了一种一锅多酶法，用于从简单糖起始材料制备寡糖。