bis(ammonium) guanosine 5'-(β-L-fucopyranosyl) diphosphate | 141017-85-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: bis(ammonium) guanosine 5'-(β-L-fucopyranosyl) diphosphate
• 英文别名: GDP-β-L-fucose diammonium salt
• CAS: 141017-85-8
• 化学式: C₁₆H₂₅N₅O₁₅P₂*2H₃N
• 分子量: 623.408
• InChiKey: ZBJZIRSXQSEUKE-ZRENREKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.44
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  346.49
• 氢给体数：
  10.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  bis(ammonium) guanosine 5'-(β-L-fucopyranosyl) diphosphate 、 2-巯基乙醇 、 2-(3'-mercaptopropionylamido)ethyl β-D-galactopyranosyl-(1->3)-O-2-acetamido-2-deoxy-β-D-glucopyranoside 在 human milk fucosyltransferase Thiopyridyl-activated Thiopropyl Sepharose 6B gel 、 sodium azide 、 sodium cacodylate 、 manganese(ll) chloride 作用下， 以 水 、 甘油 为溶剂， 反应 145.0h， 以68%的产率得到
  参考文献：
  名称：

  Solid-Phase Enzymatic Synthesis of a Lewis a Trisaccharide Using an Acceptor Reversibly Bound to Sepharose

  摘要：

  The disaccharide 2-aminoethyl O-beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside was reacted with thiobutyrolactone to give a disaccharide with a thiol group on the aglycone. This disaccharide was reacted with activated Thiopropyl Sepharose, which gave a disaccharide bound to Sepharose via a disulphide bond. Enzymatic fucosylation, using GDP-fucose and partially purified human milk fucosyltransferase, gave a trisaccharide in good yield, which was cleaved from Sepharose by treatment with mercaptoethanol or dithiothreitol.

  DOI：

  10.1080/07328309708006516
• 作为产物：
  描述：

  6-脱氧-beta-L-半乳糖 1-磷酸酯 以22%的产率得到bis(ammonium) guanosine 5'-(β-L-fucopyranosyl) diphosphate
  参考文献：
  名称：

  Stiller, Regine; Thiem, Joachim, Liebigs Annalen der Chemie, 1992, # 5, p. 467 - 472

  摘要：

  DOI：

文献信息

• 1<i>H</i>-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions:  Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose
  作者：Valentin Wittmann、Chi-Huey Wong

  DOI：10.1021/jo9620066

  日期：1997.4.1

  An improved procedure is described for the efficient and high-yield (76-91%) synthesis of nucleoside diphosphate sugars from the readily available nucleoside 5'-monophosphomorpholidate and sugar 1-phosphate in the presence of 1H-tetrazole. Comparative kinetic investigations by means of (31)P NMR spectroscopy with different additives (1,2,4-triazole, acetic acid, N-hydroxysuccinimide, 4-(dimethylamino)pyridine

  描述了一种改进的方法，用于在1H-四唑存在下，从容易获得的核苷5'-单磷酸吗啡酸酯和糖1-磷酸酯高效高效地合成核苷二磷酸糖（76-91％）。通过（31）P NMR光谱对不同添加剂（1,2,4-三唑，乙酸，N-羟基琥珀酰亚胺，4-（二甲氨基）吡啶盐酸盐，高氯酸）进行的动力学比较研究和质谱分析表明四唑起作用在焦磷酸键形成中作为酸和亲核催化剂。