[1'-(5''-deoxyuridin)-1'H-1',2',3'-triazol-4'-yl] methyl-α-D-galactopyranoside | 1152423-04-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: [1'-(5''-deoxyuridin)-1'H-1',2',3'-triazol-4'-yl] methyl-α-D-galactopyranoside
• 英文别名: 5'-deoxy-5'-[4-(α-D-galactopyranosyloxymethyl)-1,2,3-triazol-1-yl]uridine；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[[4-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]triazol-1-yl]methyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1152423-04-5
• 化学式: C₁₈H₂₅N₅O₁₁
• 分子量: 487.423
• InChiKey: BOZDNJMBXSAHCM-BXZRKBECSA-N

物化性质

• 密度：
  2.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  229
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  炔丙基alpha-D-吡喃半乳糖苷 、 5'-azido-5'-deoxyuridine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 8.0h， 以86%的产率得到[1'-(5''-deoxyuridin)-1'H-1',2',3'-triazol-4'-yl] methyl-α-D-galactopyranoside
  参考文献：
  名称：

  Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors

  摘要：

  A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding alpha-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk beta-1,4-galactosyltransferase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.001

文献信息

• Nucleoside triphosphate mimicry: a sugar triazolyl nucleoside as an ATP-competitive inhibitor of B. anthracis pantothenate kinase
  作者：Andrew S. Rowan、Nathan I. Nicely、Nicola Cochrane、Wjatschesslaw A. Wlassoff、Al Claiborne、Chris J. Hamilton

  DOI：10.1039/b909729e

  日期：——

  The synthesis of a library of nucleoside triphoshate mimetics is described where the Mg2+ chelated triphosphate sidechain is replaced by an uncharged methylene-triazole linked monosaccharide sidechain. The compounds have been evaluated as inhibitors of Bacillus anthracispantothenate kinase and a competitive inhibitor has been identified with a Ki that is 3-fold lower than the Km value of ATP.

  本文描述了一组核苷三磷酸类似物的合成，其中以中性的甲撑-三唑连接的单糖侧链取代了与Mg2+螯合的核苷三磷酸侧链。这些化合物被评估为炭疽杆菌泛酸激酶的抑制剂，并且发现一种竞争性抑制剂的Ki值比ATP的Km值低3倍。
• Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors
  作者：Kar Kheng Yeoh、Terry D. Butters、Brendan L. Wilkinson、Antony J. Fairbanks

  DOI：10.1016/j.carres.2009.01.001

  日期：2009.3

  A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding alpha-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk beta-1,4-galactosyltransferase. (C) 2009 Elsevier Ltd. All rights reserved.