(–)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose | 20513-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (–)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose
• 英文别名: (-)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose；1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose；(-)-1,2-O-isopropylidene-5-diphenylphospho-D-xylofuranose；O⁵-diphenoxyphosphoryl-O¹,O²-isopropylidene-α-D-xylofuranose；O⁵-Diphenoxyphosphoryl-O¹,O²-isopropyliden-α-D-xylofuranose
• CAS: 20513-97-7
• 化学式: C₂₀H₂₃O₈P
• 分子量: 422.372
• InChiKey: TVMCJOLKGWQXPW-FCGDIQPGSA-N

物化性质

• 沸点：
  521.8±50.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (–)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose 在 Adam’s catalyst 、 水 作用下， 以 甲醇 为溶剂， 生成 β-D-xylofuranose 5-phosphate
  参考文献：
  名称：

  Construction of the Octose 8-Phosphate Intermediate in Lincomycin A Biosynthesis: Characterization of the Reactions Catalyzed by LmbR and LmbN

  摘要：

  Lincomycin A is a potent antimicrobial agent noted for its unusual C1 methylmercapto-substituted 8-carbon sugar. Despite its long clinical history for the treatment of Gram-positive infections, the biosynthesis of the C-8-sugar, methylthiolincosamide (MTL), is poorly understood. Here, we report our studies of the two initial enzymatic steps in the MTL biosynthetic pathway leading to the identification of D-erythro-D-gluco-octose 8-phosphate as a key intermediate. Our experiments demonstrate that this intermediate is formed via a transaldol reaction catalyzed by LmbR using D-fructose 6-phosphate or D-sedoheptulose 7-phosphate as the C-3 donor and D-ribose 5-phosphate as the C-5 acceptor. Subsequent 1,2-isomerization catalyzed by LmbN converts the resulting 2-keto C-8-sugar (octulose 8-phosphate) to octose 8-phosphate. These results provide, for the first time, in vitro evidence for the biosynthetic origin of the C-8 backbone of MTL.

  DOI：

  10.1021/ja308221z
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 (–)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose
  参考文献：
  名称：

  氧化磷酸化在水中益生元合成氨基恶唑啉-5'-磷酸

  摘要：

  RNA对于地球上的所有生命都是必不可少的，并且是生命中第一种生物聚合物的主要候选物质。氨基恶唑啉最近已成为关键的益生元核糖核苷酸前体，在这里，我们开发了一种从益生元原料水中合成氨基恶唑啉-5'-磷酸的新策略。丙烯醛的氧化产生了缩水甘油醛（90％），它指导着水中的区域选择性磷酸化，并特别以高达36％的产率提供了5'-磷酸化的核苷酸前体。我们还证明了蛋白氨基酸（Met，Glu，Gln）和核苷酸合成之间的世代联系。

  DOI：

  10.1039/c7cc02183f

文献信息

• Arabinose 5-phosphate analogues as mechanistic probes for Neisseria meningitidis 3-deoxy-d-manno-octulosonate 8-phosphate synthase
  作者：Meekyung Ahn、Fiona C. Cochrane、Mark L. Patchett、Emily J. Parker

  DOI：10.1016/j.bmc.2008.09.056

  日期：2008.11

  3-Deoxy-D-manno-octulosonate 8-phosphate (KDO8P) synthase catalyses the condensation reaction between phosphoenolpyruvate and D-arabinose 5-phosphate (D-A5P) in a key step in lipopolysaccharide biosynthesis in Gram-negative bacteria. The KDO8P synthase from Neisseria meningitidis was cloned into Escherichia coli, overexpressed and purified. A variety of D-A5P stereoisomers were tested as substrates

  3-脱氧-D-甘露糖八酸八磷酸酯（KDO8P）合酶催化磷酸烯醇丙酮酸和D-阿拉伯糖5-磷酸酯（D-A5P）之间的缩合反应，这是革兰氏阴性细菌中脂多糖生物合成的关键步骤。来自脑膜炎奈瑟氏球菌的KDO8P合酶被克隆到大肠杆菌中，过表达和纯化。测试了多种D-A5P立体异构体作为底物，其中只有D-A5P和1-X5P是底物。构建了脑膜炎奈瑟氏球菌KDO8P合酶的Asn59Ala突变体，该突变体保留了不到1％的野生型活性。这些结果与该酶的催化机理一致，其中D-A5P和Asn59的C2和C3羟基至关重要。
• SYNTHESIS AND CHARACTERIZATION OF<scp>D</scp>-XYLOFURANOSE-5-PHOSPHATE
  作者：J. L. Barnwell、W. A. Saunders、R. W. Watson

  DOI：10.1139/v55-086

  日期：1955.4.1

  Phosphorylation of 1,2-O-isopropylidene-D-xylose with diphenylphosphoro-chloridate yielded crystalline 1,2-O-isopropylidene-D-xylofuranose-5-diphenyl-phosphate. Subsequent hydrogenolysis in glacial acetic acid over Adams' catalyst quantitatively removed phenyl groups as shown by infrared analysis. Mild hydrolysis in acetic acid for two hours at 80 °C. removed the isopropylidene grouping, and D-xylose-5-phosphate was isolated as an amorphous barium salt. A yield of 81% of theoretical was obtained from 1,2-O-isopropylidene-D-xylose, or an over-all yield of 72% from xylose. The product was characterized through its amorphous barium, disodium, and dipotassium salts, and its crystalline dibrucine and distrychnine salts.

  1,2-O-异丙基亚甲基-D-木糖的磷酸化反应使用二苯基磷酸氯酯生成了结晶的1,2-O-异丙基亚甲基-D-木糖呋喃糖-5-二苯基磷酸盐。随后在冰乙酸中使用亚当斯催化剂进行氢解反应，红外分析显示苯基基团被定量去除。在80°C下用冰乙酸温和水解两小时，去除了异丙基亚甲基基团，D-木糖-5-磷酸盐被分离为无定形的钡盐。从1,2-O-异丙基亚甲基-D-木糖得到了81%的理论产率，从木糖得到了总产率为72%。通过其无定形的钡盐、二钠盐和二钾盐，以及其结晶的二槲皮碱盐和马钱子碱盐对产物进行了表征。
• Gorin et al., Journal of the Chemical Society, 1955, p. 582
  作者：Gorin et al.

  DOI：——

  日期：——
• Phosphroylated Sugars. IV.¹ The Synthesis of D-Xylose 3-Phosphate via 1,2-O-Isopropylidene-D-Xylofuranose-3,5-cyclic Phosphate
  作者：J. G. Moffatt、H. G. Khorana

  DOI：10.1021/ja01562a044

  日期：1957.3