fucose 1-phosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: fucose 1-phosphate
• 英文别名: Fuc-1-P；[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl] dihydrogen phosphate
• 化学式: C₆H₁₃O₈P
• 分子量: 244.138
• InChiKey: PTVXQARCLQPGIR-SVZMEOIVSA-N

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

• 作为产物：
  描述：

  D-Fucose 在 Streptococcus pneumoniae TIGR₄ galactokinase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 反应 20.0h， 生成 fucose 1-phosphate
  参考文献：
  名称：

  Substrate specificity of galactokinase from Streptococcus pneumoniae TIGR4 towards galactose, glucose, and their derivatives

  摘要：

  Galactokinases (GalKs) have attracted significant research attention for their potential applications in the enzymatic synthesis of unique sugar phosphates. The galactokinase (GalKSpe4) cloned from Streptococcus pneumoniae TIGR4 presents a remarkably broad substrate range including 14 diverse natural and unnatural sugars. TLC and MS studies revealed that GalKSpe4 had relaxed activity towards galactose derivatives with modifications on the C-6, 4- or 2-positions. Additionally, GalKSpe4 can also tolerate glucose while glucose derivatives with modifications on the C-6, 4- or 2-positions were unacceptable. More interestingly, GalKSpe4 can phosphorylate L-mannose in moderate yield (43%), while other L-sugars such as L-Gal cannot be recognized by this enzyme. These results are very significant because there is rarely enzyme reported that can phosphorylate such uncommon substrates as L-mannose. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.095

文献信息

• 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。
• MODIFIED SIALYL LEWIS?A COMPOUNDS
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：EP0588848A1

  公开（公告）日：1994-03-30
• METHODS FOR THE SYNTHESIS OF MONOFUCOSYLATED OLIGOSACCHARIDES TERMINATING IN DI-N-ACETYLLACTOSAMINYL STRUCTURES
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：EP0591256A1

  公开（公告）日：1994-04-13
• US5770407A
  申请人：——

  公开号：US5770407A

  公开（公告）日：1998-06-23
• [EN] METHODS FOR THE SYNTHESIS OF MONOFUCOSYLATED OLIGOSACCHARIDES TERMINATING IN DI-N-ACETYLLACTOSAMINYL STRUCTURES
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：WO1992022662A1

  公开（公告）日：1992-12-23

  (EN) Disclosed are methods for the preparation of monofucosylated and sialylated derivatives of the compound $g(b)Gal(1-4)$g(b)GlcNAc(1-3)$g(b)Gal(1-4)$g(b)GlcNAc-R. In particular, the methods of this invention provide for a multi-step synthesis wherein selective monofucosylation is accomplished on the 3-hydroxy group on only one of the GlcNAc units found in the $g(b)Gal(1-4)$g(b)GlcNAc(1-3)$g(b)Gal(1-4)$g(b)GlcNAc-R compound. In this step, monofucosylation is achieved by use of the $g(a)(1-3)fucosyltransferase.(FR) On décrit des méthodes de préparation de dérivés à monofucosylation et sialylation du composé $g(b)Gal(1-4)$g(b)GlcNAc(1-3)$g(b)Gal(1-4)$g(b)GlcNAc-R. En particulier, les méthodes de ladite invention permettent une synthèse en plusieurs étapes, la monofucosylation sélective étant réalisée sur le groupe 3-hydroxy sur une seule des unités GlcNAc trouvées dans le composé $g(b)Gal(1-4)$g(b)GlcNAc(1-3)$g(b)Gal(1-4)$g(b)GlcNAc-R. Dans cette étape, la monofucosylation est réalisée par l'utilisation de la $g(a)(1-3) fucosyltransférase.