(R)-1-hydroxy-2-propyl α-glucopyranoside | 1334163-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-hydroxy-2-propyl α-glucopyranoside
• CAS: 1334163-05-1
• 化学式: C₉H₁₈O₇
• 分子量: 238.238
• InChiKey: QMTIZJYZJXBOHM-NZJLWHDDSA-N

物化性质

• 沸点：
  482.3±45.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.82
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  119.61
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (R)-1,2-丙二醇 、 对氟苯甲醇 在 盐酸 、 Leuconostoc mesenteroides sucrose phosphorylase 作用下， 以 水 为溶剂， 生成 (R)-1-hydroxy-2-propyl α-glucopyranoside 、 1-O-α-D-glucopyranosyl-3-deoxy-2(R)-deoxyglicerol
  参考文献：
  名称：

  Regio- and stereoselective glucosylation of diols by sucrose phosphorylase using sucrose or glucose 1-phosphate as glucosyl donor

  摘要：

  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.

  DOI：

  10.1016/j.molcatb.2010.08.009

文献信息

• Regioselective O-glucosylation by sucrose phosphorylase: a promising route for functional diversification of a range of 1,2-propanediols
  作者：Christiane Luley-Goedl、Thornthan Sawangwan、Lothar Brecker、Patricia Wildberger、Bernd Nidetzky

  DOI：10.1016/j.carres.2010.05.022

  日期：2010.8

  depletion of donor substrate, the hydrolysis also resulted in formation of maltose and kojibiose (up to 45%) due to secondary enzymatic glucosylation of the glucose thus produced. Using 3-ethoxy-1,2-propanediol as the acceptor substrate (1.0M), the desired transfer product was obtained in about 65% yield when employing a moderate (1.5-fold) excess of sucrose donor. Loss of the glucosyl substrate to

  1,2-丙二醇及其3-芳氧基/烷氧基衍生物是直接由甘油生产的大宗商品。糖基化是使其功能多样化成有用的精细化学品的有前途的途径。不同的1,2-丙二醇中仲羟基的区域选择性糖基化是通过蔗糖磷酸化酶催化的转移反应实现的，其中蔗糖为底物，仅获得2-O-α-d-吡喃葡萄糖基产物。用于优化生物催化合成的系统研究包括防止蔗糖水解，蔗糖水解在该过程中作为磷酸化酶的副反应而发生。除了供体底物的“非生产性”消耗外，由于由此产生的葡萄糖的二次酶促糖基化作用，水解还导致麦芽糖和曲二糖的形成（高达45％）。使用3-乙氧基-1，2-丙二醇作为受体底物（1.0M），当使用适度（1.5倍）过量的蔗糖供体时，以约65％的收率获得所需的转移产物。在这些条件下，葡糖基底物向“葡糖二糖”副产物的损失极小（<7.5％）。其他受体的反应性依次降低，3-甲氧基-1，2-丙二醇> 1,2-丙二醇> 3-烯丙氧基-1,2-丙二醇> 3-（邻甲氧基苯氧基）-1