2,5-dideoxy-3-O-α-D-glucopyranosyl-2,5-imino-D-mannitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dideoxy-3-O-α-D-glucopyranosyl-2,5-imino-D-mannitol
• 英文别名: (2r,3r,4r,5r)-4-Hydroxy-2,5-Bis(Hydroxymethyl)pyrrolidin-3-Yl Alpha-D-Glucopyranoside；(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)pyrrolidin-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₂H₂₃NO₉
• 分子量: 325.316
• InChiKey: AZDBETUGBOOBRU-BBFNFCGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  172
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dibenzyl(2-oxoethyl)phosphonate 、 2,5-dideoxy-3-O-α-D-glucopyranosyl-2,5-imino-D-mannitol 在 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 以56%的产率得到dibenzyl {[3-hydroxy-2,5-bis(hydroxymethyl)-(3-O-α-D-glucopyranosyl)pyrrolidin-1-yl]ethyl}phosphonate
  参考文献：
  名称：

  Zwitterionic pyrrolidene-phosphonates: inhibitors of the glycoside hydrolase-like phosphorylase Streptomyces coelicolor GlgEI-V279S

  摘要：

  我们合成并评估了针对α-葡聚糖水解酶类磷酸化酶链霉菌（Sco）GlgEI-V279S的新的带电离子抑制剂，该酶在α-葡聚糖生物合成中发挥作用。

  DOI：

  10.1039/c7ob00388a
• 作为产物：
  描述：

  D-(+)-纤维二糖 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 144.0h， 生成 2,5-dideoxy-3-O-α-D-glucopyranosyl-2,5-imino-D-mannitol
  参考文献：
  名称：

  Synthesis of a novel α-glucoside of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-d-mannitol via enzymatic glucosylation of 5-azido-5-deoxy-d-fructopyranose

  摘要：

  Regio- and stereoselective enzymatic glucosylation of 5-azido-5-deoxy-D-fructopyranose with the aid of commerically available alpha-glucosidase from yeast allows easy access to the corresponding 4-O-alpha-D-glucopyranosyl derivative of this non-natural ketose. This disaccharide gives, in one step, access to 2,5-dideoxy-3-O-alpha-D-glucopyranosyl-2,5-imino-D-mannitol. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02281-2

文献信息

• Synthesis of a Poly-hydroxypyrolidine-Based inhibitor of <i>Mycobacterium tuberculosis</i> GlgE
  作者：Sri Kumar Veleti、Jared J. Lindenberger、Sandeep Thanna、Donald R. Ronning、Steven J. Sucheck

  DOI：10.1021/jo501481r

  日期：2014.10.17

  in α-glucan biosynthesis. Mutation of GlgE in Mtb increases the concentration of maltose-1-phosphate (M1P), one substrate for GlgE, causing rapid cell death. We have designed 2,5-dideoxy-3-O-α-d-glucopyranosyl-2,5-imino-d-mannitol (9) to act as an inhibitor of GlgE. Compound 9 was synthesized using a convergent synthesis by coupling thioglycosyl donor 14 and 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropy

  治疗时间长、药物依从性差以及治疗结核分枝杆菌( Mtb )期间的自然选择导致广泛耐药结核病 (XDR-TB)。因此，需要确定新的抗结核药物靶点。Mtb GlgE 是一种麦芽糖基转移酶，参与 α-葡聚糖生物合成。Mtb中 GlgE 的突变会增加 1-磷酸麦芽糖 (M1P)（GlgE 的一种底物）的浓度，从而导致细胞快速死亡。我们已经设计了2,5-二脱氧-3- ö -α- d吡喃葡萄糖基-2,5-亚氨基d -mannitol（9）作为GlgE的抑制剂。化合物9通过将硫糖基供体14和 5-叠氮基-3 - O-苄基-5-脱氧-1,2 - O-异亚丙基-β - d-吡喃果糖 ( 23 )偶联形成二糖24，使用会聚合成法合成。还原和分子内还原胺化将中间体二糖24转化为所需的吡咯烷9。化合物9抑制Mtb GlgE 和天蓝色链霉菌( Sco ) GlgEI的变体，K i = 237 ± 27 μM 和K i=
• Zwitterionic pyrrolidene-phosphonates: inhibitors of the glycoside hydrolase-like phosphorylase Streptomyces coelicolor GlgEI-V279S
  作者：Sri Kumar Veleti、Cecile Petit、Donald R. Ronning、Steven J. Sucheck

  DOI：10.1039/c7ob00388a

  日期：——

  We synthesized and evaluated new zwitterionic inhibitors against glycoside hydrolase-like phosphorylaseStreptomyces coelicolor(Sco) GlgEI-V279S which plays a role in α-glucan biosynthesis.

  我们合成并评估了针对α-葡聚糖水解酶类磷酸化酶链霉菌（Sco）GlgEI-V279S的新的带电离子抑制剂，该酶在α-葡聚糖生物合成中发挥作用。
• Synthesis of a novel α-glucoside of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-d-mannitol via enzymatic glucosylation of 5-azido-5-deoxy-d-fructopyranose
  作者：Karl Dax、Michael Ebner、Roland Peinsipp、Arnold E. Stütz

  DOI：10.1016/s0040-4039(96)02281-2

  日期：1997.1

  Regio- and stereoselective enzymatic glucosylation of 5-azido-5-deoxy-D-fructopyranose with the aid of commerically available alpha-glucosidase from yeast allows easy access to the corresponding 4-O-alpha-D-glucopyranosyl derivative of this non-natural ketose. This disaccharide gives, in one step, access to 2,5-dideoxy-3-O-alpha-D-glucopyranosyl-2,5-imino-D-mannitol. Copyright (C) 1996 Elsevier Science Ltd