庚基-β-D-吡喃葡萄糖苷 | 78617-12-6

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 庚基-β-D-吡喃葡萄糖苷
• 中文别名: 庚烷基-Β-D-吡喃葡萄糖苷；庚烷基-β-D-吡喃葡萄糖苷；中文名称暂缺
• 英文名称: heptyl β-D-glucopyranoside
• 英文别名: n-heptyl β-D-glucopyranoside；n-heptyl beta-D-glucopyranoside；Heptyl beta-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-heptoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 78617-12-6
• 化学式: C₁₃H₂₆O₆
• 分子量: 278.346
• InChiKey: NIDYWHLDTIVRJT-UJPOAAIJSA-N

物化性质

• 熔点：
  74-75℃
• 稳定性/保质期：

  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  8
• 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

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29400000
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20℃保存。

制备方法与用途

n-Heptyl-β-D-glucopyranoside 是一种非离子型表面活性剂，可用于溶解膜结合蛋白（保持其天然状态），以及制备脂质体。

反应信息

• 作为反应物：
  描述：

  庚基-β-D-吡喃葡萄糖苷 在 almond meal 作用下， 以 水 为溶剂， 反应 336.0h， 生成 戊基BETA-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

  摘要：

  An array of ten beta-D-glueopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl beta-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl beta-D-glucoside was found to have significant surface activity as well.

  DOI：

  10.1016/s1872-2067(11)60333-1
• 作为产物：
  描述：

  戊基BETA-D-吡喃葡萄糖苷 在 水 作用下， 以 水 为溶剂， 反应 168.0h， 生成 庚基-β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

  摘要：

  An array of ten beta-D-glueopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl beta-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl beta-D-glucoside was found to have significant surface activity as well.

  DOI：

  10.1016/s1872-2067(11)60333-1
• 作为试剂：
  描述：

  磷酸单硝基苯基酯 在 protein tyrosine phosphatase from apple pathogen Erwinia amylovora 、 sodium chloride 、 庚基-β-D-吡喃葡萄糖苷 作用下， 以 aq. buffer 为溶剂， 生成 对硝基苯酚
  参考文献：
  名称：

  Determination and Kinetic Characterization of a New Potential Inhibitor for AmsI Protein Tyrosine Phosphatase from the Apple Pathogen Erwinia amylovora

  摘要：

  Erwinia amylovora is a Gram-negative bacterium, responsible for the fire blight disease in Rosaceae plants. Its virulence is correlated with the production of an exopolysaccharide (EPS) called amylovoran, which protects the bacterium from the surrounding environment and helps its diffusion inside the host. Amylovoran biosynthesis relies on the expression of twelve genes clustered in the ams operon. One of these genes, amsI, encodes for a Low Molecular Weight Protein Tyrosine Phosphatase (LMW-PTP) called EaAmsI, which plays a key role in the regulation of the EPS production pathway. For this reason, EaAmsI was chosen in this work as a target for the development of new antibacterial agents against E. amylovora. To achieve this aim, a set of programs (DOCK6, OpenEye FRED) was selected to perform a virtual screening using a database of ca. 700 molecules. The six best-scoring compounds identified were tested in in vitro assays. A complete inhibition kinetic characterization carried out on the most promising molecule (n-Heptyl β-D-glucopyranoside, N7G) showed an inhibition constant of 7.8 ± 0.6 µM. This study represents an initial step towards the development of new EaAmsI inhibitors able to act as antibacterial agents against E. amylovora infections.

  DOI：

  10.3390/molecules28237774

文献信息

• PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
  申请人：Philippe Michel

  公开号：US20100028280A1

  公开（公告）日：2010-02-04

  The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

  该发明涉及一种直发角蛋白纤维的拉直过程，包括：(i)将至少两种变性剂含有的拉直组合物涂抹到角蛋白纤维上的步骤，(ii)使用加热装置将角蛋白纤维的温度升高至110至250°C的步骤。
• Simple Synthesis of .BETA.-D-Glycopyranosides Using .BETA.-Glycosidase from Almonds
  作者：Katsumi Kurashima、Mikio Fujii、Yoshiteru Ida、Hiroyuki Akita

  DOI：10.1248/cpb.52.270

  日期：——

  Enzymatic glycosidation of twenty-one kinds of alcohols (n-hepanol, n-octanol, 2-phenylethanol, 3-phenylpropanol, 4-phenylbutanol, 5-phenylpentanol, 6-phenylhexanol, furfury alcohol, 2-pyridinemethanol, isobutanol, isopentanol, p-methoxycinnamylalcohol) including secondary alcohols (isopropanol, cyclohexanol, 1-phenylethanol) and 1,ω-alkanediols (1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol), salicyl alcohol and 4-nitrophenyl β-D-glucopyranoside (5) using β-glucosidase from almonds stereoselectively gave the corresponding β-D-glucopyranosides in moderate yield.

  酶促糖苷化反应对二十一种醇类（正庚醇、正辛醇、2-苯乙醇、3-苯丙醇、4-苯丁醇、5-苯戊醇、6-苯己醇、呋喃醇、2-吡啶甲醇、异丁醇、异戊醇、对甲氧基肉桂醇）进行，其中包括次级醇（异丙醇、环己醇、1-苯乙醇）和1,ω-烷二醇（1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇），水杨醇及4-硝基苯基β-D-葡萄糖吡喃苷（5），使用来自杏仁的β-葡萄糖苷酶选择性地生成了相应的β-D-葡萄糖吡喃苷，产率适中。
• POLYMER STABILIZER
  申请人：KIMURA Yoshikazu

  公开号：US20100179253A1

  公开（公告）日：2010-07-15

  A polymer stabilizer comprising the following alkoxy compound: the alkoxy compound: a compound obtained by alkoxylating at least one hydroxyl group contained in a compound of the following formula (1) containing one formyl group or carbonyl group and (n− 1 ) hydroxyl groups in the molecule with an alkyl group having 1 to 12 carbon atoms: C n H 2n O n (1) (wherein, n represents an integer of 3 or more).

  一种聚合物稳定剂，包含以下烷氧基化合物：所述烷氧基化合物是通过将含有以下通式（1）中的一个甲酰基或羰基以及分子中（n-1）个羟基的化合物中的至少一个羟基进行烷氧基化而得到的化合物，其中烷基团含有1至12个碳原子：CnH2nOn（1）（其中，n代表3或以上的整数）。
• A Solanum torvum GH3 β-glucosidase expressed in Pichia pastoris catalyzes the hydrolysis of furostanol glycoside
  作者：Rungarun Suthangkornkul、Pornpisut Sriworanun、Hiroyuki Nakai、Masayuki Okuyama、Jisnuson Svasti、Atsuo Kimura、Saengchan Senapin、Dumrongkiet Arthan

  DOI：10.1016/j.phytochem.2016.03.015

  日期：2016.7

  glucosyl hydrolase 1 (GH1) or 3 (GH3) families. Previously, a β-glucosidase (torvosidase) was purified from Solanum torvum leaves that specifically catalyzed hydrolysis of two furostanol 26-O-β-glucosides, torvosides A and H. Furostanol glycoside 26-O-β-glucosides have been reported as natural substrates of some plant GH1 enzymes. However, torvosidase was classified as a GH3 β-glucosidase, but could

  植物 β-葡萄糖苷酶通常是葡萄糖基水解酶 1 (GH1) 或 3 (GH3) 家族的成员。以前，一种 β-葡萄糖苷酶（torvosidase）是从 Solanum torvum 叶子中纯化出来的，它专门催化两种呋喃甾醇 26-O-β-葡萄糖苷、torvosides A 和 H 的水解。 糠醇糖苷 26-O-β-葡萄糖苷已被报道为天然底物一些植物GH1酶。然而，torvosidase 被归类为 GH3 β-葡萄糖苷酶，但不能水解 GH3 酶的天然底物 β-寡糖苷。在这里，通过 cDNA 末端快速扩增方法分离了编码 S. torvum β-葡萄糖苷酶 (SBgl3) 的全长 cDNA。1887bp 的 ORF 编码 629 个氨基酸，与其他植物 GH3 β-葡萄糖苷酶具有高度同源性。LC-MS/MS 确定的纯化天然 SBgl3 的内部肽序列与 SBgl3 cDNA 的推导氨基酸序列匹配，表明它编码天然酶。带有多组氨酸标签
• Preparation of alkyl α- and β-d-glucopyranosides, thermotropic properties and X-ray analysis
  作者：Volker Adasch、Bettina Hoffmann、Wolfgang Milius、Gerhard Platz、Gundula Voss

  DOI：10.1016/s0008-6215(98)00302-4

  日期：1998.12

  Monohydrates of heptyl to decyl α- d -glucopyranosides as obtained from product mixtures of the Fischer glucosylation were crystallized from water at the Krafft point. The results of the single-crystal X-ray analysis of anhydrous α anomers and their monohydrates provide for a better understanding of crystal formation and stability of their hydrates. The preparation of alkyl β- d -glucopyranosides—without

  摘要从Fischer葡萄糖基化产物混合物中获得的庚基到癸基α-d-吡喃葡萄糖苷一水合物在克拉夫特点从水中结晶。无水α端基异构体及其一水合物的单晶X射线分析结果可更好地理解其水合物的晶体形成和稳定性。已经描述了烷基β-d-吡喃葡萄糖苷的制备-没有伴随形成副产物α-端基异构体。已经研究了α化合物及其一水合物和β-d-吡喃葡萄糖苷的热致性质。

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