(2R,3S,4S,5R)-2-(hydroxymethyl)-6-(2-methylpropoxy)oxane-3,4,5-triol | 145033-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R)-2-(hydroxymethyl)-6-(2-methylpropoxy)oxane-3,4,5-triol
• CAS: 145033-16-5
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: MJQQYLKJAGVSNG-ZKZCYXTQSA-N

物化性质

• 熔点：
  113-114 °C
• 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

• 作为产物：
  描述：

  异丁醇 、 4-硝基苯-Β-D-吡喃葡萄糖苷 在 Dalbergia cochinchinensis Pierre dalcochinase N₁₈₉F mutant 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.08h， 以90%的产率得到(2R,3S,4S,5R)-2-(hydroxymethyl)-6-(2-methylpropoxy)oxane-3,4,5-triol
  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

• Verfahren zur Herstellung von Alkylglucosiden
  申请人：BASF Aktiengesellschaft

  公开号：EP0102558A1

  公开（公告）日：1984-03-14

  Die Erfindung betrifft ein Verfahren zur Herstellung von Alkylglucosiden durch Acetalisierung von Glucose mit der zumindest äquivalenten Menge an einem C3- bis Cs-Alkanol in Gegenwart eines sauren Katalysators, bei dem man die Acetalisierung in Gegenwart einer dem Katalysator mindestens äquivalenten Menge eines Alkalimetallsalzes einer Borsäure durchführt. Die erhaltnen Alkylglucoside können direkt z.B. als Lösungsvermittler vor allem im kosmetischen Bereich eingesetzt oder zu höheren Alkylglucosiden weiter umgesetzt werden.

  本发明涉及一种在酸性催化剂存在下通过葡萄糖与至少等量的 C3 至 Cs 烷醇缩醛反应生产烷基葡糖苷的工艺，其中缩醛反应是在至少与催化剂等量的硼酸碱金属盐存在下进行的。 得到的烷基葡糖苷可以直接使用，例如作为增溶剂，特别是在化妆品领域，或者进一步转化为更高的烷基葡糖苷。
• ANTI-WRINKLE AGENT AND ADAM INHIBITOR
  申请人：Shiseido Company, Ltd.

  公开号：EP2127636A1

  公开（公告）日：2009-12-02

  Disclosed is an anti-wrinkle agent for ameliorating a wrinkle (particularly a fine wrinkle) developed when the barrier function is decreased by dryness and the like. Also disclosed is an ADAM inhibitor. The anti-wrinkle agent or the ADAM inhibitor comprises an alkyl glucoside represented by the general formula: (1) [wherein R represents a linear or branched alkyl group having 1 to 18 carbon atoms] or a salt thereof.

  本发明公开了一种抗皱剂，用于改善因干燥等原因导致屏障功能降低时产生的皱纹（尤其是细小皱纹）。还公开了一种 ADAM 抑制剂。抗皱剂或 ADAM 抑制剂包括由通式表示的烷基葡萄糖苷：(1) [其中 R 代表具有 1 至 18 个碳原子的直链或支链烷基]或其盐。
• VERWENDUNG VON ACETALDEHYDACETALEINHEITEN ENTHALTENDEN POLYACETALEN IN WASCH- UND REINIGUNGSMITTELN
  申请人：BASF Aktiengesellschaft

  公开号：EP0663932B1

  公开（公告）日：1997-05-07
• US4704453A
  申请人：——

  公开号：US4704453A

  公开（公告）日：1987-11-03
• US5520834A
  申请人：——

  公开号：US5520834A

  公开（公告）日：1996-05-28