uridine 5'-(α-D-fucopyranosyl diphosphate) | 16375-63-6

• 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'-(α-D-fucopyranosyl diphosphate)
• 英文别名: UDP-6-deoxy-Gal；UDP-Fuc；[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl] hydrogen phosphate
• CAS: 16375-63-6
• 化学式: C₁₅H₂₄N₂O₁₆P₂
• 分子量: 550.307
• InChiKey: DRDCJEIZVLVWNC-ABVWGUQPSA-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：

  uridine 5'-(α-D-fucopyranosyl diphosphate) 、 毛地黄毒苷配基 以 二甲基亚砜 为溶剂， 反应 16.0h， 以4.5%的产率得到evomonoside
  参考文献：
  名称：

  Synthesis of Uridine 5′-(α-D-Fucopyranosyl Diphosphate) and (Digitoxigenin-3β-yl)-β-D-Fucopyranoside and Enzymatic β-D-Fucosylation of Cardenolide Aglycones in Digitalis lanata1

  摘要：

  The phosphorylation of 2,3,4-tri-O-acetyl-alpha-D-fucopyranose with o-phenylene phosphochloridate yielded alpha-D-fucopyranosyl phosphate which was used for condensation with uridine 5'-monophosphomorpholidate to give uridine 5'-(alpha-D-fucopyranosyl diphosphate) (UDP-alpha-D-fucose). A crude enzyme preparation from young leaves of Digitalis lanata EHRH has been shown to catalyze the transfer of D-fucose from synthetic UDP-alpha-D-fucose to cardenolide aglycones, such as digitoxigenin. The reaction product was identified and characterized by chemical synthesis, HPLC, and spectral methods as the 3 beta-O-beta-D-fucopyranoside of digitoxigenin (digiproside). (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1012
• 作为产物：
  描述：

  D-Fucose 在 吡啶 、 2,4,6-三甲基吡啶 、 lead(IV) acetate 、 sodium hydroxide 、 Dowex 1X₈ (HCO₃^-) 、 氨 、 水 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 146.0h， 生成 uridine 5'-(α-D-fucopyranosyl diphosphate)
  参考文献：
  名称：

  Synthesis of Uridine 5′-(α-D-Fucopyranosyl Diphosphate) and (Digitoxigenin-3β-yl)-β-D-Fucopyranoside and Enzymatic β-D-Fucosylation of Cardenolide Aglycones in Digitalis lanata1

  摘要：

  The phosphorylation of 2,3,4-tri-O-acetyl-alpha-D-fucopyranose with o-phenylene phosphochloridate yielded alpha-D-fucopyranosyl phosphate which was used for condensation with uridine 5'-monophosphomorpholidate to give uridine 5'-(alpha-D-fucopyranosyl diphosphate) (UDP-alpha-D-fucose). A crude enzyme preparation from young leaves of Digitalis lanata EHRH has been shown to catalyze the transfer of D-fucose from synthetic UDP-alpha-D-fucose to cardenolide aglycones, such as digitoxigenin. The reaction product was identified and characterized by chemical synthesis, HPLC, and spectral methods as the 3 beta-O-beta-D-fucopyranoside of digitoxigenin (digiproside). (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1012

文献信息

• Enzymic transfer of 6-modified d-galactosyl residues: synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-d-galactose residues at the nonreducing end and evaluation of 6-deoxy-d-galactosyl transfer to glycoprotein using bovine β-(1 → 4)-galactosyltransferase and UDP-6-deoxy-d-galactose
  作者：Yasuhiro Kajihara、Tsuyoshi Endo、Hiroyuki Ogasawara、Hisashi Kodama、Hironobu Hashimoto

  DOI：10.1016/0008-6215(94)00369-q

  日期：1995.4

  UDP-6-Deoxy-D-galactose and UDP-6-deoxy-6-fluoro-D-galactose were synthesized and their transfer to 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine) by beta-(1 --> 4)galactosyltransferase was examined. The transfer rates of 6-deoxy-D-galactose and 6-deoxy-6-fluoro-D-galactose were 1.3 and 0.2% of that of D-galactosyl transfer, respectively. The 2-acetamido-4-O-(6-deoxy-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranose (6'-deoxy-N-acetyllactosamine) and methyl 2-acetamido-4-O-(6-deoxy-6-fluoro-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranoside (6'-deoxy-6'-fluoro-N-acetyllactosamine) were synthesized enzymatically in 30 and 59% yields, respectively. Further, 6-deoxy-D-galactose could be completely transferred to N-linked type biantennary oligosaccharides having two N-acetyl-D-glucosaminyl residues at the nonreducing end to give the corresponding penta- and hepta-saccharides in 55 and 57% yields, respectively. An assay of 6-deoxy-D-galactosyl transfer using asialo agalacto alpha(1)-acid glycoprotein as an acceptor suggested that 6-deoxy-D-galactose was transferred to about 30% of the N-acetyl-D-glucosaminyl residues in the N-linked oligosaccharides of the glycoprotein.
• One-pot three-enzyme synthesis of UDP-Glc, UDP-Gal, and their derivatives
  作者：Yang Zou、Mengyang Xue、Wenjun Wang、Li Cai、Leilei Chen、Jun Liu、Peng George Wang、Jie Shen、Min Chen

  DOI：10.1016/j.carres.2013.03.005

  日期：2013.5

  A UTP-glucose-1-phosphate uridylyltransferase (SpGalU) and a galactokinase (SpGalK) were cloned from Streptococcus pneumoniae TIGR4 and were successfully used to synthesize UDP-galactose (UDP-Gal), UDPglucose (UDP-Glc), and their derivatives in an efficient one-pot reaction system. The reaction conditions for the one-pot multi-enzyme synthesis were optimized and nine UDP-Glc/Gal derivatives were synthesized. Using this system, six unnatural UDP-Gal derivatives, including UDP-2-deoxy-Galactose and UDP-GalN(3) which were not accepted by other approach, can be synthesized efficiently in a one pot fashion. More interestingly, this is the first time it has been reported that UDP-Glc can be synthesized in a simpler one-pot three-enzyme synthesis reaction system. (C) 2013 Elsevier Ltd. All rights reserved.
• Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides
  作者：Taketo Uchiyama、Ole Hindsgaul

  DOI：10.1080/07328309808001892

  日期：1998.11

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).
• Biosynthesis of nucleotide sugars by a promiscuous UDP-sugar pyrophosphorylase from Arabidopsis thaliana (AtUSP)
  作者：Jun Liu、Yang Zou、Wanyi Guan、Yafei Zhai、Mengyang Xue、Lan Jin、Xueer Zhao、Junkai Dong、Wenjun Wang、Jie Shen、Peng George Wang、Min Chen

  DOI：10.1016/j.bmcl.2013.04.090

  日期：2013.7

  Nucleotide sugars are activated forms of monosaccharides and key intermediates of carbohydrate metabolism in all organisms. The availability of structurally diverse nucleotide sugars is particularly important for the characterization of glycosyltransferases. Given that limited methods are available for preparation of nucleotide sugars, especially their useful non-natural derivatives, we introduced herein an efficient one-step three-enzyme catalytic system for the synthesis of nucleotide sugars from monosaccharides. In this study, a promiscuous UDP-sugar pyrophosphorylase (USP) from Arabidopsis thaliana (AtUSP) was used with a galactokinase from Streptococcus pneumoniae TIGR4 (SpGalK) and an inorganic pyrophosphatase (PPase) to effectively synthesize four UDP-sugars. AtUSP has better tolerance for C4-derivatives of Gal-1-P compared to UDP-glucose pyrophosphorylase from S. pneumoniae TIGR4 (SpGalU). Besides, the nucleotide substrate specificity and kinetic parameters of AtUSP were systematically studied. AtUSP exhibited considerable activity toward UTP, dUTP and dTTP, the yield of which was 87%, 85% and 84%, respectively. These results provide abundant information for better understanding of the relationship between substrate specificity and structural features of AtUSP. (C) 2013 Elsevier Ltd. All rights reserved.