2-deoxy-2-fluoro-α-D-galactopyranosyl phosphate | 209005-34-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-fluoro-α-D-galactopyranosyl phosphate
• 英文别名: [(2R,3R,4S,5R,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate
• CAS: 209005-34-5
• 化学式: C₆H₁₀FO₈P
• 分子量: 260.113
• InChiKey: LXEHNDWFCMGWAY-VFUOTHLCSA-L

物化性质

• 沸点：
  565.148±60.00 °C(Press: 760.00 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  16
• 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：
  142
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  尿苷-5'-三磷酸 、 2-deoxy-2-fluoro-α-D-galactopyranosyl phosphate 在 pyrophosphatase 、 UDP-glucose pyrophosphorylase 、 galactose-1-phosphate uridyltransferase 作用下， 反应 72.0h， 以67%的产率得到uridine 5'-diphospho-2-deoxy-2-fluoro-α-D-galactose
  参考文献：
  名称：

  Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases

  摘要：

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00139-5
• 作为产物：
  描述：

  (2R,3R,4R)-2-(羟基甲基)-3,4-二氢-2H-吡喃-3,4-二醇 在 2(1H)-喹啉酮,1-丙基- 、 乙酸激酶(-20℃) 1-chloromethyl-4-fluoro-1,4-diazonia-bicyclo<2.2.2>octane ditriflate 、 磷酰基乙酸 、 5’-三磷酸腺苷 、 bovine albumin 作用下， 以 水 为溶剂， 反应 99.0h， 生成 2-deoxy-2-fluoro-α-D-galactopyranosyl phosphate
  参考文献：
  名称：

  Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases

  摘要：

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00139-5

文献信息

• Chemoenzymatic synthesis of mono- and di-fluorinated Thomsen–Friedenreich (T) antigens and their sialylated derivatives
  作者：Jun Yan、Xi Chen、Fengshan Wang、Hongzhi Cao

  DOI：10.1039/c2ob26989a

  日期：——

  Fluorinated Thomsen–Friedenreich (T) antigens were synthesized efficiently from chemically produced fluorinated monosaccharides using a highly efficient one-pot two-enzyme chemoenzymatic approach containing a galactokinase and a D-galactosyl-β1–3-N-acetyl-D-hexosamine phosphorylase. These fluorinated T-antigens were further sialylated to form fluorinated ST-antigens using a one-pot two-enzyme system

  氟化 Thomsen-Friedenreich (T) 抗原是使用含有半乳糖激酶和D-半乳糖基-β1-3- N-乙酰-D-己糖胺磷酸化酶的高效一锅双酶化学酶法从化学生产的氟化单糖有效合成的。使用含有 CMP-唾液酸合成酶和 α-2-3-唾液酸转移酶的一锅双酶系统将这些氟化 T 抗原进一步唾液酸化以形成氟化 ST 抗原。
• Rapid Screening of Diverse Biotransformations for Enzyme Evolution
  作者：Emily E. Kempa、James L. Galman、Fabio Parmeggiani、James R. Marshall、Julien Malassis、Clement Q. Fontenelle、Jean-Baptiste Vendeville、Bruno Linclau、Simon J. Charnock、Sabine L. Flitsch、Nicholas J. Turner、Perdita E. Barran

  DOI：10.1021/jacsau.1c00027

  日期：2021.4.26

  of enzymes, in different formats, achieving sample throughputs equivalent to ∼40 s per sample. The heat map output allows rapid selection of active enzymes within 96-well plates facilitating identification of industrially relevant biocatalysts. This DiBT-MS screening workflow has been applied to the directed evolution of a phenylalanine ammonia lyase (PAL) as a case study, enhancing its activity toward

  缺乏无标签的高通量筛选技术的缺乏成为鉴定活性和选择性生物催化剂的主要瓶颈，变异体的数量通常超过了传统分析平台在实际时间范围内评估其活性的能力。在这里，我们展示了将生物转化直接输注到质谱仪（DiBT-MS）筛查中应用到各种格式的多种酶的过程，每个样品的样品通量约为40 s。热图输出允许在96孔板内快速选择活性酶，从而有助于鉴定工业上相关的生物催化剂。作为案例研究，该DiBT-MS筛选工作流程已应用于苯丙氨酸氨裂合酶（PAL）的定向进化，增强了其对富含电子的肉桂酸衍生物的活性，这些衍生物与木质纤维素生物质的降解有关。筛选平台的其他好处包括发现具有新颖活性的生物催化剂（激酶，亚胺还原酶），并引入了离子迁移技术，可以更加可靠地鉴定产品。
• Enzymatic synthesis of UDP-(3-deoxy-3-fluoro)-d-galactose and UDP-(2-deoxy-2-fluoro)-d-galactose and substrate activity with UDP-galactopyranose mutase
  作者：John N. Barlow、John S. Blanchard

  DOI：10.1016/s0008-6215(00)00135-x

  日期：2000.10

  The novel UDP-sugar uridine 5'-(3-deoxy-3-fluoro-D-galactopyranosyl diphosphate) (I) and UDP-(2-deoxy-2-fluoro)-D-galactose (2) have been prepared enzymatically and tested as substrate analogues for the enzyme UDP-galactopyranose mutase (UDP-Galp mutase EC 5.4.99.9). Turnover of both 1 and 2 by UDP-Galp mutase was observed by HPLC and F-19 NMR. The HPLC elution profile and F-19 chemical shift of the products are consistent with the formation of the predicted furanose forms of 1 and 2. The K-m values for compounds 1 and 2 were similar to those of the natural substrate UDP-Galp (0.26 mM for 1, 0.2 mM for 2, and 0.6 mM for UDP-Galp), but the values for k(cat) were substantially different (1.6/min for I, 0.02/min for 2, and 1364/min for UDP-Galp). A correlation was also observed between the equilibrium yield of product formed during turnover of UDP-sugar by UDP-Galp mutase (UDP-Galp, compound 1 or compound 2), and the amount of furanose present for the free sugar at thermal equilibrium in aqueous solution, using H-1 and F-19 NMR spectroscopy. The implications of these results to the mechanism of the unusual enzymatic reaction are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases
  作者：Michael D Burkart、Stéphane P Vincent、Arno Düffels、Brion W Murray、Steven V Ley、Chi-Huey Wong

  DOI：10.1016/s0968-0896(00)00139-5

  日期：2000.8

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.