α-D-Glcp-(1->2)-D-glycol | 5887-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-Glcp-(1->2)-D-glycol
• 英文别名: 1-O-<2-Hydroxy-ethyl>-β-D-glucopyranosid；Glykol-mono-α-D-glucopyranosid；(2-hydroxy-ethyl)-α-D-glucopyranoside；(2-Hydroxy-aethyl)-α-D-glucopyranosid；(2S,3R,4S,5S,6R)-2-(2-hydroxyethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 5887-88-7
• 化学式: C₈H₁₆O₇
• 分子量: 224.211
• InChiKey: SMORULFPMBCEPX-CBQIKETKSA-N

物化性质

• 熔点：
  100-102 °C(Solv: ethanol (64-17-5); acetone (67-64-1))
• 沸点：
  490.8±45.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  15
• 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：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  葡萄糖 、 乙二醇 在 cation exchanger 作用下， 生成 α-D-Glcp-(1->2)-D-glycol
  参考文献：
  名称：

  Janson; Lindberg, Acta Chemica Scandinavica (1947), 1959, vol. 13, p. 138,142

  摘要：

  DOI：

文献信息

• Catalytic Iron(III) Chloride Mediated Site-Selective Protection of Mono- and Disaccharides and One Trisaccharide
  作者：Alexandra Gouasmat、Aurélie Lemétais、Julien Solles、Yann Bourdreux、Jean-Marie Beau

  DOI：10.1002/ejoc.201700538

  日期：2017.6.23

  Regioselective differentiation of the hydroxy groups of mono- and oligosaccharide substrates is necessary to form building blocks that can be used for synthetic transformations. In this paper, we show that iron(III) chloride hexahydrate catalyses the tandem protection of mono- and disaccharides to give, in a one-pot procedure, selectively protected carbohydrate building blocks. This tandem protocol

  单糖和寡糖底物的羟基的区域选择性分化对于形成可用于合成转化的结构单元是必需的。在本文中，我们表明六水合氯化铁（III）可以催化一糖和二糖的串联保护，从而在一锅法中提供选择性保护的糖类结构单元。该串联方案已成功应用于三糖。该程序易于执行；为了获得最佳结果，每种碳水化合物底物都需要对一锅反应条件进行微调。
• [EN] SYNTHESIS AND USE OF GLYCOSIDE PRO-DRUG ANALOGS<br/>[FR] SYNTHÈSE ET UTILISATION D'ANALOGUES GLYCOSIDES DE PROMÉDICAMENT
  申请人：NUTEK PHARMA LTD

  公开号：WO2012142141A1

  公开（公告）日：2012-10-18

  The present invention relates to methods and compositions for the synthesis, production, and use of pro-drug analogs. This invention relates to a method for the production of a broad group of glycosylated drugs, including but not limited to propofol, acetaminophen, and camptothecin carbohydrate derivatives.

  本发明涉及用于合成、生产和使用前药类似物的方法和组合物。本发明涉及一种用于生产包括但不限于丙泊酚、对乙酰氨基酚和喜树碱糖衍生物在内的广泛群体的糖基药物的方法。
• Interaction of (1→4)- and (1→6)-linked disaccharides with the fenton reagent under physiological conditions
  作者：Koji Uchida、Shunro Kawakishi

  DOI：10.1016/s0008-6215(00)90805-x

  日期：1988.2

  (1→4)-linked disaccharides. About 35–40% of (1→6)-and 15–20% of (1→4)-linked disaccharides were oxidatively degraded to smaller molecules after incubation for 24 h. Of the four disaccharides examined, namely, maltose, isomaltose, cellobiose, and gentiobiose, the α-(1→6)-linked disaccharide isomaltose exhibited the highest reactivity, whereas the β-(1→4)-linked disaccharide cellobiose showed the lowest

  摘要研究了在生理条件下，以麦芽糖和异麦芽糖为主的（1→4）-和（1→6）连接的二糖与Fenton试剂的反应。通过glc和glc-ms的三甲基甲硅烷基衍生物对氧化产物进行化学表征，结果表明（1→6）连接的二糖与芬顿试剂产生的羟基自由基（·OH）的反应性大于（1）。 →4）-连接的二糖。孵育24小时后，约35-40％（1→6）-和15-20％（1→4）连接的二糖被氧化降解成较小的分子。在所检查的四种二糖中，即麦芽糖，异麦芽糖，纤维二糖和龙胆二糖，α-（1→6）连接的二糖异麦芽糖表现出最高的反应性，而β-（1→4）连接的二糖纤维二糖表现出最低的反应性。 。
• Protein Engineering of Glucosylglycerol Phosphorylase Facilitating Efficient and Highly Regio- and Stereoselective Glycosylation of Polyols in a Synthetic System
  作者：Tong Zhang、Pi Liu、Hongli Wei、Xinming Sun、Yan Zeng、Xuewen Zhang、Yi Cai、Mengfei Cui、Hongwu Ma、Weidong Liu、Yuanxia Sun、Jiangang Yang

  DOI：10.1021/acscatal.2c05232

  日期：2022.12.16

  O-Glycosylation of polyols attracts great interest in manufacturing chiral polyol glucosides available in cosmetics and detergent industries. Achieving synchronously controlled regio- and stereoselectivities in glycosylation of polyols remains challenging. Here, we discovered that the glucosylglycerol phosphorylase from Marinobacter adhaerens (MaGGP) presented broad catalytic promiscuity in glycosylation

  多元醇的O-糖基化引起了人们对制造可用于化妆品和洗涤剂行业的手性多元醇葡糖苷的极大兴趣。在多元醇的糖基化中实现同步控制的区域选择性和立体选择性仍然具有挑战性。在这里，我们发现来自Marinobacter adhaerens的葡萄糖基甘油磷酸化酶(MaGGP) 在各种多元醇的糖基化中表现出广泛的催化混杂性，特别是对于高碳 1,2-二醇，具有出色的区域选择性和立体选择性。然后，我们克服了酶工程中众所周知的活性-稳定性权衡问题，同时将 MaGGP 的热稳定性和催化效率分别提高了 1200 倍和 13.7 倍。晶体结构分析和分子动力学模拟揭示了增强的热稳定性和催化效率的起源。此外，我们提出了一种无 ATP 且热力学有利的多酶系统，用于以廉价淀粉作为糖基供体的多元醇糖基化，并成功合成了几种具有高转化率的多元醇糖苷。顺式糖苷。
• Regio- and stereoselective glucosylation of diols by sucrose phosphorylase using sucrose or glucose 1-phosphate as glucosyl donor
  作者：Rokus Renirie、Aliaksei Pukin、Barend van Lagen、Maurice C.R. Franssen

  DOI：10.1016/j.molcatb.2010.08.009

  日期：2010.12

  Previously it has been shown that glycerol can be regioselectively glucosylated by sucrose phosphorylase from Leuconostoc mesenteroides to form 2-O-alpha-D-glucopyranosyl-glycerol (Coedl et al., Angew. Chem. Int. Ed. 47 (2008) 10086-10089). A series of compounds related to glycerol were investigated by us to determine the scope of the alpha-glucosylation reaction of sucrose phosphorylase. Both sucrose and glucose 1-phosphate (GIP) were applied as glucosyl donor. Mono-alcohols were not accepted as substrates but several 1,2-diols were readily glucosylated, proving that the vicinal diol unit is crucial for activity. The smallest substrate that was accepted for glucosylation appeared to be ethylene glycol, which was converted to the monoglucoside for 69%. Using high acceptor and donor concentrations :up to 2.5 M), sucrose or GIP hydrolysis (with H2O being the 'acceptor') can be minimised. In the study cited above, a preference for glucosylation of glycerol on the 2-position has been observed. For 1,2-propanediol however, the regiochemistry appeared to be dependent on the configuration of the substrate. The (R)enantiomer was preferentialy glucosylated on its 1-position (ratio 2.5:1), whereas the 2-glucoside is the major product for (S)-1,2-propanediol (1:4.1). d.e.(p)s of 71-83% were observed with a preference for the (S)-enantiomer of the glucosides of 1,2-propanediol and 1,2-butanediol and the (R)-enantiomer of the glucoside of 3-methoxy-1,2-propanediol. This is the first example of stereoselective glucosylation of a non-natural substrate by sucrose phosphorylase. 3-Amino-1,2-propanediol, 3-chloro-1,2-propanediol, 1-thioglycerol and glyceraldehyde were not accepted as substrates. Generally, the glucoside yield is higher when sucrose is used as a donor rather than GIP. due to the fact that the released phosphate is a stronger inhibitor of the enzyme (in case of Cl P) than the released fructose (in case of sucrose). Essentially the same results are obtained with sucrose phosphorylase from Blfidobacterium adolescentis. (C) 2010 Elsevier B.V. All rights reserved.