α-D-Galactofuranosyl phosphate | 153809-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-Galactofuranosyl phosphate
• 英文别名: galactofuranosyl 1-phosphate；[(2R,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl] dihydrogen phosphate
• CAS: 153809-68-8
• 化学式: C₆H₁₃O₉P
• 分子量: 260.138
• InChiKey: HCJGGGKBFSKUFL-DGPNFKTASA-N

物化性质

• 沸点：
  668.3±65.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  α-D-Galactofuranosyl phosphate 在 HEPES buffer 作用下， 生成 UDP-Galf
  参考文献：
  名称：

  Development of a coupled spectrophotometric assay for GlfT2, a bifunctional mycobacterial galactofuranosyltransferase

  摘要：

  As a key constituent of their protective cell wall all mycobacteria produce a large structural component, the mycolylarabinogalactan (mAG) complex, which has at its core a galactan moiety of alternating beta-(1 -> 5) and beta-(1 -> 6) galactofuranosyl residues. Galactan biosynthesis is essential for mycobacterial viability and thus inhibitors of the enzymes involved in its assembly are potential drugs for the treatment of mycobacterial diseases, including tuberculosis. Only two galactofuranosyltransferases, GIfTl and GlfT2, are responsible for the biosynthesis of the entire galactan domain of the mAG and we report here the first high-throughput assay for GlfT2. Successful implementation of the assay required the synthesis of multi-milligram amounts of the donor for the enzyme, UDP-Galf, 1, which was achieved using a chemoenzymatic approach. We also describe an improved expression system for GlfT2, which provides a larger amount of active protein for the assay. Kinetic analysis of I and a known trisaccharide acceptor for the enzyme, 2, have been carried out and the apparent K-m and k(cat) values obtained for the latter are in agreement with those obtained using a previously reported radiochemical assay. The assay has been implemented in 384-well microtiter plates, which will facilitate the screening of large numbers of potential GlfT2 inhibitors, with possible utility as novel anti-TB drugs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.023
• 作为产物：
  描述：

  [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-phosphonooxyoxolan-2-yl]ethyl] benzoate 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 α-D-Galactofuranosyl phosphate
  参考文献：
  名称：

  The first chemical synthesis of UDP-α-D-galactofuranose

  摘要：

  尿苷5'-二磷酸α-D-半乳糖呋喃糖，可能是自然界中D-半乳糖呋喃糖残基的生物化学供体，由α-D-半乳糖呋喃糖磷酸和尿苷5'-单磷酸合成。

  DOI：

  10.1039/b000210k

文献信息

• General One-Step Synthesis of Free Hexofuranosyl 1-Phosphates Using Unprotected 1-Thioimidoyl Hexofuranosides
  作者：Ronan Euzen、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1021/jo0484934

  日期：2005.2.1

  synthesis of hexofuranosyl 1-phosphates starting from new unprotected glycofuranosyl donors. It required first the preparation of new 1-thiohexofuranosides bearing a thioimidoyl heterocycle as a leaving group. The presence of sulfur and/or nitrogen atom(s) on the aglycon allowed remote activation of these thioglycofuranosides by anhydrous phosphoric acid and led to the target phosphates 9, 27, 29, and 30

  从新的未保护的糖呋喃糖基供体开始，开发了用于合成呋喃糖基1-磷酸酯的一般的一步策略。它首先需要制备带有硫代酰亚胺基杂环作为离去基团的新的1-硫己呋喃呋喃糖苷。硫和/或氮原子（一个或多个）上的糖苷配基的存在使得这些thioglycofuranosides的远程激活通过无水磷酸，并导致目标磷酸盐9，27，29，和30具有良好的选择性至极好的选择性，更重要的是，环扩展非常有限或没有。此外，通过避免对带负电荷的化合物进行任何繁琐的保护基操作并着重于简单但通用的纯化程序，可以显着改善这一一步的磷酸化反应。该方法被用于d-半乳糖和d-呋喃呋喃糖基1-磷酸的非对映控制合成，还用于制备稀有的差向异构体和/或脱氧对应物，即d-甘露糖醛和d-呋喃呋喃糖基衍生物。
• The first chemical synthesis of UDP-α-D-galactofuranose
  作者：Yury E. Tsvetkov、Andrei V. Nikolaev

  DOI：10.1039/b000210k

  日期：——

  Uridine 5′-diphosphate α-D-galactofuranose, which is likely to be a biochemical donor of D-galactofuranosyl residues in Nature, is synthesized from α-D-galactofuranosyl phosphate and uridine 5′-monophosphate.

  尿苷5'-二磷酸α-D-半乳糖呋喃糖，可能是自然界中D-半乳糖呋喃糖残基的生物化学供体，由α-D-半乳糖呋喃糖磷酸和尿苷5'-单磷酸合成。
• Development of a coupled spectrophotometric assay for GlfT2, a bifunctional mycobacterial galactofuranosyltransferase
  作者：Natisha L. Rose、Ruixiang Blake Zheng、Jean Pearcey、Ruokun Zhou、Gladys C. Completo、Todd L. Lowary

  DOI：10.1016/j.carres.2008.03.023

  日期：2008.8

  As a key constituent of their protective cell wall all mycobacteria produce a large structural component, the mycolylarabinogalactan (mAG) complex, which has at its core a galactan moiety of alternating beta-(1 -> 5) and beta-(1 -> 6) galactofuranosyl residues. Galactan biosynthesis is essential for mycobacterial viability and thus inhibitors of the enzymes involved in its assembly are potential drugs for the treatment of mycobacterial diseases, including tuberculosis. Only two galactofuranosyltransferases, GIfTl and GlfT2, are responsible for the biosynthesis of the entire galactan domain of the mAG and we report here the first high-throughput assay for GlfT2. Successful implementation of the assay required the synthesis of multi-milligram amounts of the donor for the enzyme, UDP-Galf, 1, which was achieved using a chemoenzymatic approach. We also describe an improved expression system for GlfT2, which provides a larger amount of active protein for the assay. Kinetic analysis of I and a known trisaccharide acceptor for the enzyme, 2, have been carried out and the apparent K-m and k(cat) values obtained for the latter are in agreement with those obtained using a previously reported radiochemical assay. The assay has been implemented in 384-well microtiter plates, which will facilitate the screening of large numbers of potential GlfT2 inhibitors, with possible utility as novel anti-TB drugs. (C) 2008 Elsevier Ltd. All rights reserved.