(2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate | 798554-50-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate
• 英文别名: dibenzyl {methyl [(2S,3R)-4-hydroxy-2,3-(isopropylidenedioxy)]butan-1-oat-4-yl} phosphate；methyl (4S,5R)-5-[bis(phenylmethoxy)phosphoryloxymethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 798554-50-4
• 化学式: C₂₂H₂₇O₈P
• 分子量: 450.425
• InChiKey: HZNRQEOXWRRCDE-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate 在 锂硼氢 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以82%的产率得到dibenzyl (2S,3R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl phosphate
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase

  摘要：

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.

  DOI：

  10.1021/jo0516786
• 作为产物：
  描述：

  亚磷酸三苄酯 在 吡啶 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase

  摘要：

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.

  DOI：

  10.1021/jo0516786

文献信息

• Substrate analogs for the investigation of deoxyxylulose 5-phosphate reductoisomerase inhibition: synthesis and evaluation
  作者：Chanokporn Phaosiri、Philip J. Proteau

  DOI：10.1016/j.bmcl.2004.08.023

  日期：2004.11

  Deoxyxylulose 5-phosphate (DXP) analogs were synthesized and evaluated as alternative substrates and inhibitors of recombinant Synechocystis PCC6803 DXP reductoisomerase (DXR; EC 1.1.1.267). Five of the compounds tested (1,2-dideoxy-D-threo-3-hexulose 6-phosphate, 1-deoxy-l-ribulose 5-phosphate, 2S,3R-dihydroxybutyramide 4-phosphate, 4S-hydroxypentan-2-one 5-phosphate, and 3S-hydroxypentan-2-one 5-phosphate)

  合成了5-磷酸脱氧木酮糖（DXP）类似物，并评估了重组拟南芥PCC6803 DXP还原异构酶（DXR; EC 1.1.1.267）的替代底物和抑制剂。测试的化合物中的五种（1,2-二脱氧-D-苏--3-己糖6-磷酸酯，1-脱氧-1-核糖5-磷酸酯，2S，3R-二羟基丁酰胺4-磷酸酯，4S-羟基戊烷-2-酮与磷霉素相比，5-磷酸和3S-羟基戊-2--2-酮（5-磷酸）起相对较弱的竞争性抑制剂的作用。第六种化合物3R，4S-二羟基-5-氧己基膦酸用作替代底物，最近有报道称该化合物与大肠杆菌DXR相同。
• Synthesis and Evaluation of 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphoric Acid Analogues as Alternate Substrates for Methylerythritol Phosphate Synthase
  作者：David T. Fox、C. Dale Poulter

  DOI：10.1021/jo048022h

  日期：2005.3.1

  [GRAPHICS]Four deoxyxylulose phosphate (DXP) analogues were synthesized and evaluated as substrates/ inhibitors for methylerythritol phosphate (MEP) synthase. In analogues CF3-DXP (1), CF2-DXP (2), and CF-DXP (3), the three methyl hydrogens at Cl of DXP were sequentially replaced by fluorine. In the fourth analogue, Et-DXP (4), the methyl group in DXP was replaced by an ethyl moiety. Analogues 1, 2, and 4 were not substrates for MEP synthase under normal catalytic conditions and were instead modest inhibitors with IC50 values of 2.0, 3.4, and 6.2 mM, respectively. In contrast, 3 was a good substrate (k(cat) = 38 s(-1), K-m = 227 mu M) with a turnover rate similar to that of the natural substrate. These results are consistent with a retro-aldol/aldol mechanism rather than an a-ketol rearrangement for the enzyme-catalyzed conversion of DXP to MEP.