bis(triethylammonium) β-L-fucopyranosyl 1-phosphate | 128473-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(triethylammonium) β-L-fucopyranosyl 1-phosphate
• 英文别名: β-L-fucose-1-phosphate bis(triethylammonium) salt；bis(triethylammonium) β-L-fucopyranosyl phosphate；bistriethylammonium β-L-fucopyranosyl phosphate
• CAS: 128473-11-0
• 化学式: C₆H₁₃O₈P*2C₆H₁₅N
• 分子量: 446.522
• InChiKey: SSOBPFKMOQIPPF-AHXHKAPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  139.92
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  bis(triethylammonium) β-L-fucopyranosyl 1-phosphate 、 以 吡啶 为溶剂， 反应 168.0h， 以33%的产率得到uridine-5'-(β-L-fucopyranosyl)-diphosphate, bis(triethylammonium) salt
  参考文献：
  名称：

  Synthesis of unnatural sugar nucleotides and their evaluation as donor substrates in glycosyltransferase-catalyzed reactions

  摘要：

  New unnatural sugar nucleotides, UDP-Fuc and CDP-Fuc were synthesized from fucose-beta-1-phosphate and nucleotide monophosphates activated as morpholidates. Furthermore, a nucleotide analogue was prepared by phosphorylation of 1-(beta-D-ribofuranosyl)cyan uric acid, itself obtained as a protected derivative by condensation of the persilylated derivative of cyanuric acid with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose in 74% yield. This phosphate activated according to the same procedure was condensed with fucose-beta-1-phosphate, affording a new sugar nucleotide conjugate (NDP-Fuc) which was evaluated together with UDP-Fuc, CDP-Fuc and ADP-Fuc, as facose donors in alpha-(1-->4/3)-fucosyltransferase (FucT-III) catalyzed reaction. Fucose transfer could be observed with each of the donors and kinetic parameters were determined using a fluorescent acceptor substrate. Efficiency of the four analogues towards FucT-III was in the following order: UDP-Fuc = ADP-Fuc > NDP-Fuc > CDP-Fuc.According to the same strategy ADP-GlcNAc was prepared from AMP-morpholidate and N-acetylglucosamine-alpha-1-phosphate; tested as a glucosaminyl donor towards Neisseria meningitidis N-acetylglucosaminyl transferase (LgtA), ADP-GlcNAc was recognized with 0.1% efficiency as compared with UDP-GlcNAc, the natural donor substrate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.09.002
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-α-L-fucopyranosyl trichloroacetimidate 在 钯 水 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 bis(triethylammonium) β-L-fucopyranosyl 1-phosphate
  参考文献：
  名称：

  Schmidt, Richard R.; Wegmann, Barbara; Jung, Karl-Heinz, Liebigs Annalen der Chemie, 1991, # 2, p. 121 - 124

  摘要：

  DOI：

文献信息

• The synthesis and characterization of α- and (β-<scp>L</scp>-fucopyranosyl phosphates and GDP fucose
  作者：Hernan A. Nunez、John V. O'Connor、Paul R. Rosevear、Robert Barker

  DOI：10.1139/v81-304

  日期：1981.7.15

  from fucose. This synthesis was made possible by increasing the yield of the key intermediate, β-L-fucopyranosyl phosphate, five-fold over that previously reported (Prihar and Behrman. Biochemistry, 12, 997 (1973)), by utilizing guanosine 5′-phosphoric di-n-butylphosphinothioic anhydride (Furusawa et al. J. Chem. Soc. Perkin Trans I, 171 (1976)) or GMP morpholdate for the synthesis of GDPFuc, and by

  鸟苷二磷酸岩藻糖 (GDPFuc) 已从岩藻糖中化学合成，总产率为 40%。通过利用鸟苷 5'-磷酸将关键中间体 β-L-吡喃岩藻糖基磷酸酯的产率提高到先前报道的 5 倍（Prihar 和 Behrman. Biochemistry, 12, 997 (1973)），使该合成成为可能。二正丁基硫代膦酸酐 (Furusawa et al. J. Chem. Soc. Perkin Trans I, 171 (1976)) 或 GMP morpholdate 用于合成 GDPFuc，并通过改进分离中间体和最终产品的方法。在 pH 值为 3 时，GDPFuc 降解为 GDP，其半衰期在 37 °C 下为 7 小时，在 4 °C 下为 52 小时。在 pH 值介于 5 和 8 之间时，7 天后降解率低于 10%。在 pH 7.5 的 0.2 M PIPES 缓冲液中，20 mM Mn2+ 和 Mg2+
• 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。
• Synthesis of Guanosine 5′-(β-L-Fucopyranosyl)-Diphosphate Revisited
  作者：B. M. Heskamp、H. J.G. Broxterman、G. A. van der Marel、J. H. van Boom

  DOI：10.1080/07328309608005678

  日期：1996.7

  It will be demonstrated that a successful synthesis of beta-L-fucopyranose-1-phosphate (2), a key intermediate in the preparation of guanosine 5'-(beta-L-fucopyranose)-diphosphate (1), strongly depends on the nature of the acyl protecting groups for the non-anomeric hydroxyl functions. Thus, the perbenzoylated, instead of peracetylated, alpha-L-fucopyranosyl trichloroacetimidate (11) or the corresponding ethyl beta-thiofucopyranoside proved to be a convenient starting compound for the preparation of 2. Further, condensation of N,N'-dicyclohexyl-4-morpholinecarboxamidinium guanosine 5'-morpholidophosphate with excess 2 gave the title compound without concomitant formation of bisguanosine-5'-diphosphate (16).
• Solid-Phase Enzymatic Synthesis of a Lewis a Trisaccharide Using an Acceptor Reversibly Bound to Sepharose
  作者：O. Blixt、T. Norberg

  DOI：10.1080/07328309708006516

  日期：1997.2

  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.
• Efficient chemical synthesis of GDP-fucose
  作者：Yoshitaka Ichikawa、Mui Mui Sim、Chi Huey Wong

  DOI：10.1021/jo00036a036

  日期：1992.5