UDP-β-L-fucose

• 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: UDP-β-L-fucose
• 英文别名: uridine 5'-diphosphate-β-L-fucoside；guanosine 5′-diphospho-β-L-fucose；GDP-Fuc；[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] hydrogen phosphate
• 化学式: C₁₅H₂₄N₂O₁₆P₂
• 分子量: 550.307
• InChiKey: DRDCJEIZVLVWNC-WPNYMCDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  271
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  、 UDP-β-L-fucose 在 calf intestine alkaline phosphatase 、 lactosamine α-1,3/4 fucosyltransferase 5 、 manganese(ll) chloride 作用下， 以 aq. buffer 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  不对称多天线人乳寡糖的合成

  摘要：

  尽管哺乳动物聚糖通常具有高度复杂的不对称多天线结构，但是化学和化学酶法合成几乎仅集中在制备更简单的对称结构上。这种缺陷妨碍了对聚糖结合蛋白生物学的研究，这反过来使这类生物的生物医学应用复杂化。分子。在这里，我们描述了一种酶促策略，使用有限数量的人糖基转移酶来访问60种不对称，多天线的人乳寡糖（HMO）的集合，这些糖被用于开发聚糖微阵列。用几种聚糖结合蛋白探测阵列发现，不仅末端的糖表位而且聚糖的复杂结构都可以以意想不到的方式影响结合选择性。N-和O-连接的聚糖表达HMO的结构元件，因此，所报道的合成原理将具有广泛的适用性。

  DOI：

  10.1073/pnas.1701785114
• 作为产物：
  描述：

  1,2,3,4-四-O-苯甲酰基-6-脱氧吡喃己糖 在 水 、 三溴化磷 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 26.5h， 生成 UDP-β-L-fucose
  参考文献：
  名称：

  Stereoselective Chemical Synthesis of Sugar Nucleotides via Direct Displacement of Acylated Glycosyl Bromides

  摘要：

  The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-alpha-d-mannose as well as UDP- and GDP-beta-l-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates.

  DOI：

  10.1021/ol063068d

文献信息

• Unusually Broad Substrate Tolerance of a Heat-Stable Archaeal Sugar Nucleotidyltransferase for the Synthesis of Sugar Nucleotides
  作者：Rahman M. Mizanur、Corbin J. Zea、Nicola L. Pohl

  DOI：10.1021/ja046070d

  日期：2004.12.1

  Herein, we report the first cloning, recombinant expression, and synthetic utility of a sugar nucleotidyltransferase from any archaeal source and demonstrate by an electrospray ionization mass spectrometry (ESI-MS)-based assay its unusual tolerance of heat, pH, and sugar substrates. The metal-ion-dependent enzyme from Pyrococcus furiosus DSM 3638 showed a relatively high degree of acceptance of glucose-1-phosphate (Glc1P), mannose-1-phosphate(Man1P), galactose-1-phosphate (Gal1P), fucose-1-phosphate, glucosamine-1-phosphate, galactosamine-1-phosphate, and N-acetylglucosamine-1-phosphate with uridine and deoxythymidine triphosphate (UTP and dTTP, respectively). The apparent Michaelis constants for Glc1P, Man1P, and Gal1P are 13.0 +/- 0.7, 15 +/- 1, and 22 +/- 2 muM, respectively, with corresponding turnover numbers of 2.08, 1.65, and 1.32 s(-1), respectively. An initial velocity study indicated an ordered bi-bi catalytic mechanism for this enzyme. The temperature stability and inherently broad substrate tolerance of this archaeal enzyme promise an effective reagent for the rapid chemoenzymatic synthesis of a range of natural and unnatural sugar nucleotides for in vitro glycosylation studies and highlight the potential of archaea as a source of new enzymes for synthesis.
• Synthesis of asymmetrical multiantennary human milk oligosaccharides
  作者：Anthony R. Prudden、Lin Liu、Chantelle J. Capicciotti、Margreet A. Wolfert、Shuo Wang、Zhongwei Gao、Lu Meng、Kelley W. Moremen、Geert-Jan Boons

  DOI：10.1073/pnas.1701785114

  日期：2017.7.3

  architectures, chemical and chemoenzymatic synthesis has almost exclusively focused on the preparation of simpler symmetrical structures. This deficiency hampers investigations into the biology of glycan-binding proteins, which in turn complicates the biomedical use of this class of biomolecules. Herein, we describe an enzymatic strategy, using a limited number of human glycosyltransferases, to access a collection

  尽管哺乳动物聚糖通常具有高度复杂的不对称多天线结构，但是化学和化学酶法合成几乎仅集中在制备更简单的对称结构上。这种缺陷妨碍了对聚糖结合蛋白生物学的研究，这反过来使这类生物的生物医学应用复杂化。分子。在这里，我们描述了一种酶促策略，使用有限数量的人糖基转移酶来访问60种不对称，多天线的人乳寡糖（HMO）的集合，这些糖被用于开发聚糖微阵列。用几种聚糖结合蛋白探测阵列发现，不仅末端的糖表位而且聚糖的复杂结构都可以以意想不到的方式影响结合选择性。N-和O-连接的聚糖表达HMO的结构元件，因此，所报道的合成原理将具有广泛的适用性。
• Stereoselective Chemical Synthesis of Sugar Nucleotides via Direct Displacement of Acylated Glycosyl Bromides
  作者：Shannon C. Timmons、David L. Jakeman

  DOI：10.1021/ol063068d

  日期：2007.3.1

  The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-alpha-d-mannose as well as UDP- and GDP-beta-l-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates.