3-hydroxybenzyl β-D-glucopyranoside | 143995-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxybenzyl β-D-glucopyranoside
• 英文别名: 3-hydroxybenzyl 1-O-β-D-glucopyranoside；(3-Hydroxyphenyl)methyl beta-D-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(3-hydroxyphenyl)methoxy]oxane-3,4,5-triol
• CAS: 143995-98-6
• 化学式: C₁₃H₁₈O₇
• 分子量: 286.282
• InChiKey: PNRKIXSZTUCIJN-UJPOAAIJSA-N

物化性质

• 沸点：
  548.5±50.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲基[羟基-(3,4,5-三羟基四氢吡喃-2-基)氧基磷酰]磷酸氢酯 、 3-hydroxybenzyl β-D-glucopyranoside 在 plant xylosyltransferase from Catharanthus roseus 作用下， 反应 36.0h， 以66%的产率得到3-hydroxybenzyl β-primeveroside
  参考文献：
  名称：

  Enzymatic resolution of (RS)-1-phenylalkyl β-d-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-d-glucosides via plant xylosyltransferase

  摘要：

  The stereoselective xylosylation of (RS)-1-phenylalkyl beta-D-glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of (RS)-1-phenylethyl beta-D-glucoside afforded (R)-1-phenylethyl beta-primeveroside and (S)-1-phenylethyl beta-D-glucoside. The (R)-selective xylosylation of (RS)-1-phenylbutyl beta-D-glucoside also occurred to give (R)-1-phenylbutyl p-primeveroside and recovered (S)-1-phenylbutyl beta-D-glucoside. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.023
• 作为产物：
  描述：

  纤维素二糖 、 3-羟基苯甲醇 以 水 、 乙腈 为溶剂， 反应 72.0h， 生成 3-hydroxybenzyl β-D-glucopyranoside
  参考文献：
  名称：

  Enzyme-catalysed synthesis of alkyl β-D-Glucosides in organic media.

  摘要：

  The synthetic potential of Almond beta-D-Glucosidase for the synthesis of alkyl glucosides was studied. The regio and stereoselectivity of the synthesis were analysed for the reverse hydrolysis and the transglucosylation methods in tert-butanol and acetonitrile media.

  DOI：

  10.1016/s0040-4039(00)61314-x

文献信息

• Diversification of phenolic glucosides by two UDP-glucosyltransferases featuring complementary regioselectivity
  作者：Fei Guo、Xingwang Zhang、Cai You、Chengjie Zhang、Fengwei Li、Nan Li、Yuwei Xia、Mingyu Liu、Zetian Qiu、Xianliang Zheng、Li Ma、Gang Zhang、Lianzhong Luo、Fei Cao、Yingang Feng、Guang-Rong Zhao、Wei Zhang、Shengying Li、Lei Du

  DOI：10.1186/s12934-022-01935-w

  日期：——

  pharmaceutical demands. Microbial synthetic biology offers promising strategies for synthesis and diversification of plant glycosides. In this study, the two efficient UDP-glucosyltransferases (UGTs) (UGT85A1 and RrUGT3) of plant origin, that are capable of recognizing phenolic aglycons, are characterized in vitro. The two UGTs show complementary regioselectivity towards the alcoholic and phenolic hydroxyl groups

  葡糖苷类天然产物已显示出巨大的药用价值和潜力。然而，通过植物提取、化学合成和传统的生物转化生产糖苷已不足以满足快速增长的制药需求。微生物合成生物学为植物苷的合成和多样化提供了有前景的策略。在这项研究中，能够识别酚苷配基的两种植物来源的高效 UDP-葡萄糖基转移酶 (UGT)（UGT85A1 和 RrUGT3）在体外进行了表征。两种 UGT 对酚类底物上的醇和酚羟基显示出互补的区域选择性。通过将开发的烷基酚生物氧化系统与这些 UGT 相结合，二十四种酚糖苷是由容易获得的烷基酚底物酶促合成的。基于生物氧化和糖基化系统，构建了多个微生物细胞工厂并将其应用于生物转化，产生了多种植物和类植物O-糖苷。值得注意的是，这两种UGTs制备的几种非天然O-糖苷表现出比临床使用的糖苷类药物包括天麻素、红景天苷和螺旋体更好的脯氨酰内肽酶抑制和/或抗炎活性。此外，这两种UGT还能够催化N-和S-糖苷键的形成以产生
• Enzymatic resolution of (RS)-1-phenylalkyl β-d-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-d-glucosides via plant xylosyltransferase
  作者：Kei Shimoda、Hisashi Katsuragi

  DOI：10.1016/j.tetasy.2010.07.023

  日期：2010.8

  The stereoselective xylosylation of (RS)-1-phenylalkyl beta-D-glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of (RS)-1-phenylethyl beta-D-glucoside afforded (R)-1-phenylethyl beta-primeveroside and (S)-1-phenylethyl beta-D-glucoside. The (R)-selective xylosylation of (RS)-1-phenylbutyl beta-D-glucoside also occurred to give (R)-1-phenylbutyl p-primeveroside and recovered (S)-1-phenylbutyl beta-D-glucoside. (C) 2010 Elsevier Ltd. All rights reserved.
• Enzyme-catalysed synthesis of alkyl β-D-Glucosides in organic media.
  作者：Gabin Vic、Daniel Thomas

  DOI：10.1016/s0040-4039(00)61314-x

  日期：1992.8

  The synthetic potential of Almond beta-D-Glucosidase for the synthesis of alkyl glucosides was studied. The regio and stereoselectivity of the synthesis were analysed for the reverse hydrolysis and the transglucosylation methods in tert-butanol and acetonitrile media.