butan-2-O-β-D-glucopyranoside | 58044-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: butan-2-O-β-D-glucopyranoside
• 英文别名: sec-butyl-β-D-glucoside；s-Butyl-β-D-glucopyranosid；(2R,3R,4S,5S,6R)-2-butan-2-yloxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 58044-56-7
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: SPMHDJVTXLHOTJ-MZLYOKELSA-N

物化性质

• 熔点：
  75-76 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  404.6±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 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：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  butan-2-O-β-D-glucopyranoside 在 phosphate buffer 、 almond-β-glucosidase 作用下， 反应 24.0h， 生成 (S)-(+)-2-丁醇 、 (R)-(-)-2-丁醇
  参考文献：
  名称：

  Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

  摘要：

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.022
• 作为产物：
  描述：

  葡萄糖 、 仲丁醇 在 Fusarium solani β-glucosidase immobilized on chitosan 作用下， 以 aq. acetate buffer 为溶剂， 反应 48.0h， 生成 butan-2-O-β-D-glucopyranoside
  参考文献：
  名称：

  A novel sec-butyl-β-d-cellobioside and sec-butyl-β-d-glucoside biosynthesized by immobilized β-glucosidase of Fusarium solani with surfactant properties

  摘要：

  The immobilization of Fusarium solani beta-glucosidase (FBgl1) on chitosan was performed to improve biocatalyst performance. Compared with free FBgl1, the immobilized biocatalyst exhibited a shift of the optimal temperature, a conservation of the optimum pH with high residual activity at extreme acidic pH and an improved thermal stability. The immobilized enzyme was reusable up to 12 cycles. The FBgl1 immobilization enhanced its glucose and organic solvent tolerance. The free form of FBgl1 was unable to synthesize alkylglucosides, while the immobilized one was able to react using butanol as alcohol and either cellobiose or glucose as glucoside. The alkylglucosides were characterized by nuclear magnetic resonance as sec-butyl-beta-D-glucoside and sec-butyl-beta-D-solani-cellobioside. It is worth noting that this last glucomolecule is synthesized for the first time using an enzymatic process. These butylglucosides exhibited a typical surfactant behavior (surface tension 26-35 mN/m and critical micellar concentration 250-1000 mg/L).

  DOI：

  10.1016/j.apcata.2020.117713

文献信息

• Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst
  作者：Goutam Guchhait、Anup Kumar Misra

  DOI：10.1016/j.catcom.2011.07.016

  日期：2011.10

  Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield. (C) 2011 Elsevier B.V. All rights reserved.
• Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases
  作者：Kei Shimoda、Naoji Kubota、Hiroki Hamada

  DOI：10.1016/j.tetasy.2004.06.022

  日期：2004.8

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.
• A novel sec-butyl-β-d-cellobioside and sec-butyl-β-d-glucoside biosynthesized by immobilized β-glucosidase of Fusarium solani with surfactant properties
  作者：Manel Boudabbous、Raoudha Ben Ameur、Ines Belhaj、Meriam Cheffi、Hafeth Belghith、Noureddine Allouche、Mohamed Chamkha、Ali Gargouri

  DOI：10.1016/j.apcata.2020.117713

  日期：2020.7

  The immobilization of Fusarium solani beta-glucosidase (FBgl1) on chitosan was performed to improve biocatalyst performance. Compared with free FBgl1, the immobilized biocatalyst exhibited a shift of the optimal temperature, a conservation of the optimum pH with high residual activity at extreme acidic pH and an improved thermal stability. The immobilized enzyme was reusable up to 12 cycles. The FBgl1 immobilization enhanced its glucose and organic solvent tolerance. The free form of FBgl1 was unable to synthesize alkylglucosides, while the immobilized one was able to react using butanol as alcohol and either cellobiose or glucose as glucoside. The alkylglucosides were characterized by nuclear magnetic resonance as sec-butyl-beta-D-glucoside and sec-butyl-beta-D-solani-cellobioside. It is worth noting that this last glucomolecule is synthesized for the first time using an enzymatic process. These butylglucosides exhibited a typical surfactant behavior (surface tension 26-35 mN/m and critical micellar concentration 250-1000 mg/L).