2'-butyl D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-butyl D-glucopyranoside
• 英文别名: (3R,4S,5S,6R)-2-butan-2-yloxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: SPMHDJVTXLHOTJ-VXIHOVOASA-N

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：

  2'-butyl D-glucopyranoside 、 乙酸酐 反应 2.0h， 生成 2'-butyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 、 2-butyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst

  摘要：

  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.

  DOI：

  10.1016/j.catcom.2011.07.016
• 作为产物：
  描述：

  仲丁醇 、 4-硝基苯-Β-D-吡喃葡萄糖苷 在 Manihot esculenta Crantz linamarase 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.08h， 以65%的产率得到2'-butyl D-glucopyranoside
  参考文献：
  名称：

  Substrate specificity in hydrolysis and transglucosylation by family 1 β-glucosidases from cassava and Thai rosewood

  摘要：

  Thai rosewood (Dalbergia cochinchinensis Pierre) dalcochinase and cassava (Manihot esculenta Crantz) linamarase are glycoside hydrolase family 1 beta-glucosidases with 47% amino acid sequence identity. Each enzyme can hydrolyze its natural substrate, dalcochinin-8'-O-beta-D-glucoside and linamarin, respectively, but not the natural substrate of the other enzyme. Linamarase can transfer glucose to primary, secondary and tertiary alcohols with high efficiency, while dalcochinase can transglucosylate primary and secondary alcohols at moderate levels. In this study, eight amino acid residues in the aglycone binding pocket of dalcochinase were individually replaced with the corresponding residues of linamarase, in order to identify residues that may account for their catalytic differences. The residues 1185 and V255 of dalcochinase appeared important for its substrate specificity, with their respective mutations resulting in 24- and 12-fold reductions in K-cat/K-m for the hydrolysis of dalcochinin-8'-O-beta-D-glucoside. Transglucosylation activity was improved when 1185, N189 and V255 of dalcochinase were replaced with A201, F205 and F271 of linamarase, respectively, suggesting these residues support transglucosylation in linamarase. Among these three mutants, only the N189F mutant showed significant increases in the rate constants for the reactivation of trapped glucosyl-enzyme intermediates by all alcohols. Together, our results suggest that both hydrophobicity and geometry are important determinants for substrate specificity in hydrolysis and transglucosylation by these family 1 beta-glucosidases. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.09.003

文献信息

• Monosaccharides as internal probes for the determination of the absolute configuration of 2-butanol
  作者：Patrycja Seroka、Marcin Płosiński、Jacek Czub、Paweł Sowiński、Jan Pawlak

  DOI：10.1002/mrc.1735

  日期：2006.2

  with molecular modeling and appropriate heteronuclear long‐range coupling measurements and combined with analysis of dipolar couplings observed in NOESY spectra allowed the assignment of absolute configuration in the aglycones of elucidated α‐glycosides. Copyright © 2005 John Wiley & Sons, Ltd.

  D-葡萄糖、D-甘露糖和 L-鼠李糖与 2-丁醇的外消旋混合物反应，所得 α-糖苷通过 1H NMR 和 COZY 和 NOESY 实验进行分析。使用分子建模和适当的异核长程耦合测量进行的 α-糖苷键的构象分析，并结合 NOESY 光谱中观察到的偶极耦合分析，可以确定已阐明的 α-糖苷的苷元中的绝对构型。版权所有 © 2005 John Wiley & Sons, Ltd.
• PROCEDE DE FABRICATION ENZYMATIQUE D'$g(a)-GLUCOSIDES ET D'ESTERS D'$g(a)-GLUCOSIDES, ET UTILISATIONS DES PRODUITS AINSI OBTENUS
  申请人：ULICE S.A.

  公开号：EP0605453A1

  公开（公告）日：1994-07-13
• Procédé de fabrication enzymatique d'alpha-glucosides et de leurs esters
  申请人：ULICE S.A.

  公开号：EP0605453B1

  公开（公告）日：1997-01-08
• US5773256A
  申请人：——

  公开号：US5773256A

  公开（公告）日：1998-06-30
• [EN] METHOD FOR THE ENZYMATIC PRODUCTION OF (ALPHA)-GLUCOSIDES AND ESTERS OF (ALPHA)-GLUCOSIDES, AND UTILIZATIONS OF PRODUCTS THUS OBTAINED
  申请人：ULICE SA

  公开号：WO1993004185A1

  公开（公告）日：1993-03-04

  (EN) The present invention relates to a method for the enzymatic production of $g(a)-glucosides, characterized by contacting at least one alcohol whose only functional group or groups is/are a hydroxyl group or groups, with starch, maltodextrines or maltose, in the presence of a purified enzymatic preparation having an $g(a)-transglucosylation activity. The invention relates also to an enzymatic method for the esterification of the $g(a)-glucosides thus obtained.(FR) La présente invention concerne un procédé de fabrication enzymatique d'$g(a)-glucosides, caractérisé par la mise en contact d'au moins un alcool dont le(s) seul(s) groupement(s) fonctionnel(s) est(sont) un(des) groupement(s) hydroxyl, avec de l'amidon, des maltodextrines ou du maltose, en présence d'une préparation enzymatique purifiée présentant une activité d'$g(a)-transglucosylation. L'invention concerne également un procédé enzymatique d'estérification des $g(a)-glucosides ainsi obtenus.