α-L-fucopyranosyl phosphate | 40591-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-L-fucopyranosyl phosphate
• 英文别名: α-L-Fucopyranosylphosphat；α-L-Fucose-1-phosphat；alpha-L-fucose 1-phosphate；[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] dihydrogen phosphate
• CAS: 40591-52-4
• 化学式: C₆H₁₃O₈P
• 分子量: 244.138
• InChiKey: PTVXQARCLQPGIR-KGJVWPDLSA-N

物化性质

• 沸点：
  519.4±60.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  α-L-fucopyranosyl phosphate 、 尿苷-5'-三磷酸 在 Pyrococcus furious enzyme 、 magnesium 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 UDP-fructose
  参考文献：
  名称：

  One-Step Synthesis of Labeled Sugar Nucleotides for Protein O-GlcNAc Modification Studies by Chemical Function Analysis of an Archaeal Protein

  摘要：

  Herein we present the chemical function analysis of a recombinant sugar nucleotidyltransferase from the hyperthermophile Pyrococcus furiosus and its use in the one-pot synthesis of chloroacetyl- and alkyne-tagged analogues of uridinediphospho-N-acetylglucosamine (UDP-GlcNAc). The gene was originally annotated as a glucose-1-phosphate deoxythymidylyltransferase; however, kinetic analysis of a panel of sugar-1-phosphates with the protein shows that it is better described as a bifunctional protein that synthesizes UDP-GlcNAc from glucosamine-1-phosphate and acetyl coenzyme A (CoA). A new mass-spectrometry-based assay for the rapid analysis of the acyltransferase activity demonstrates that the enzyme can also accept cheaper truncated N-acetylcysteamine thioester substrates in place of the natural acetyl CoA. The enzyme can tolerate alkyne or chloride substitutions in the acyl moiety, thereby allowing the facile synthesis of tagged sugar nucleotides for future use in protein O-GlcNAc modification studies.

  DOI：

  10.1021/ja044117p
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-α-L-fucopyranose 在 palladium on activated charcoal 四氮唑 、 叔丁基过氧化氢 、 Dowex 50W Na⁺-form 、 氨 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.66h， 生成 α-L-fucopyranosyl phosphate
  参考文献：
  名称：

  通过亚磷酸酯中间体合成α-1-呋喃核糖基磷酸单酯和二酯的方法

  摘要：

  氯-β-氰基乙基-N，N-二异丙基氨基-亚磷酰胺试剂与适当保护的（苄基）α-L-呋喃二糖的异头羟基平滑反应，以高收率提供相对稳定的亚磷酸酯中间体。后者可以容易地转化为有价值的α-L-呋喃核糖基磷酸单酯和二酯。

  DOI：

  10.1016/s0040-4039(00)84219-7

文献信息

• One-Step, Stereocontrolled Synthesis of Glycosyl 1-Phosphates, Uridine-5‘-diphosphogalactose, and Uridine-5‘-diphosphoglucose from Unprotected Glycosyl Donors
  作者：Stephen Hanessian、Pu-Ping Lu、Hideki Ishida

  DOI：10.1021/ja982783i

  日期：1998.12.1

  α-l-fucosyl 1-phosphate. An alternative method that relies on neighboring group participation allowed the preparation of a protected β-l-fucosyl 1-phosphate. Reaction of unprotected β-d-glucopyranosyloxy and β-d-galactopyranosyloxy MOP donors with uridine diphosphoric acid gave UDP-Glc and UDP-Gal with preponderance of the desired α-anomeric configuration.

  2-(1,2-反式吡喃糖氧基)-3-甲氧基吡啶（MOP 糖苷）与磷酸反应生成相应的 1,2-cis-1-磷酸酯，收率高，立体选择性好。α-d-吡喃葡萄糖、α-d-吡喃半乳糖和2-叠氮基-2-脱氧-α-d-吡喃半乳糖的1-磷酸酯因此在不求助于保护基团的情况下制备。在 l-岩藻糖系列中，主要产品是 α-l-岩藻糖基 1-磷酸。一种依赖于相邻基团参与的替代方法允许制备受保护的 β-l-岩藻糖基 1-磷酸。未保护的 β-d-吡喃葡萄糖基氧基和 β-d-吡喃半乳糖氧基 MOP 供体与尿苷二磷酸的反应得到 UDP-Glc 和 UDP-Gal，其中主要是所需的 α-异头构型。
• Methods and products for the synthesis of oligosaccharide structures on glycoproteins, glycolipids, or as free molecules, and for the isolation of cloned genetic sequences that determine these structures
  申请人：The Regents of the University of Michigan

  公开号：US20020102688A1

  公开（公告）日：2002-08-01

  A method for isolating a gene, comprising: (i) isolating a cell possessing a post-translational characteristic of interest, said post-translational characteristic being the presence of a membrane-bound oligosaccharide or polysaccharide of interest on the surface of said cell, the presence of a soluble oligosaccharide or polysaccharide of interest in an extract of said cell, or the presence of a particularly glycosyltransferase activity in an extract of said cell; (ii) creating a genetic library of either cDNA or genomic DNA from the genetic material of said isolated cell; (iii) transforming host cells with said genetic library; and (iv) screening said transformed host cells for a host cell containing said post-translational characteristic, thereby obtaining a cell containing said gene, is disclosed. The method can be used to obtain genes encoding glycosyltransferases.

  一种分离基因的方法，包括：（i）分离具有感兴趣的后翻译特征的细胞，该后翻译特征是感兴趣的膜结合寡糖或多糖在该细胞表面的存在，感兴趣的寡糖或多糖在该细胞提取物中的存在，或者在该细胞提取物中具有特定的糖基转移酶活性；（ii）从所分离的细胞的遗传物质中创建cDNA或基因组DNA的基因库；（iii）将宿主细胞转化为该基因库；和（iv）筛选所转化的宿主细胞，以获得包含该基因的细胞，从而获得包含该基因的细胞。该方法可用于获得编码糖基转移酶的基因。
• Verfahren zur stereoselektiven Herstellung von beta-Fucopyranosylphosphaten und sehr reiner GDP-Fucose
  申请人：MERCK PATENT GmbH

  公开号：EP0502298A2

  公开（公告）日：1992-09-09

  Die Erfindung betrifft ein Verfahren zur stereoselektiven Herstellung von β-L-Fucopyranosyl-phosphaten über die Trichloracetimidate der geschützten L-Fucose und die Synthese und Aufreinigung von sehr reiner GDP-Fucose aus den β-L-Fucopyranosyl-phosphaten.

  本发明涉及一种通过受保护 L-岩藻糖的三氯乙酰亚氨酸盐立体选择性生产 β-L-岩藻糖基磷酸酯的工艺，以及从 β-L-岩藻糖基磷酸酯合成和纯化高纯度 GDP-岩藻糖的工艺。
• EP0654082A4
  申请人：——

  公开号：EP0654082A4

  公开（公告）日：1997-01-02
• CLONING AND EXPRESSION OF A HUMAN $g(a)(1,3)FUCOSYLTRANSFERASE, FUCT-VI
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP0654082A1

  公开（公告）日：1995-05-24