N-octyl-β-D-glucopyranosylamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-octyl-β-D-glucopyranosylamine
• 英文别名: N-octyl-β-D-glucosylamine；OcGPA；N-octyl-beta-D-glucopyranosylamine；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(octylamino)oxane-3,4,5-triol
• 化学式: C₁₄H₂₉NO₅
• 分子量: 291.388
• InChiKey: IWKCFHUUBBYMNV-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-octyl-β-D-glucopyranosylamine 在 重水 作用下， 反应 168.0h， 生成
  参考文献：
  名称：

  Synthesis ofN-Alkyl-β-d-glucosylamines and Their Antimicrobial Activity againstFusarium proliferatum,Salmonellatyphimurium, andListeria innocua

  摘要：

  In this study, different N-alkyl-beta-D-glucosylamines were evaluated for both antifungal and antibacterial activity against Fusarium proliferatum (INRA, MUCL 1807.7), Listeria innocua (ISTAB, Universite Bordeaux 1), and Salmonella typhimurium (Institut Pasteur 5858). The tested glucosylamines were beta-D-glucosylamine (GPA), N-ethyl-beta-D-glucosylamine (EtGPA), N-butyl-beta-D-glucosylamine (BuGPA), N-hexyl-beta-D-glucosylamine (HeGPA), N-octyl-beta-D-glucosylamine (OcGPA), N-dodecyl-beta-D-glucosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucosylamine (HEtGPA), N,N-di(2-hydroxyethyl)-beta-D-glucosylamine (DHEtGPA) and N,N-diethyl-beta-D-glucosylamine (DEtGPA). The effectiveness of N-alkyl length, N-substitution, and N-hydroxyalkyl groups on both antibacterial and antifungal activity were evaluated. Results indicated that these compounds exhibited different biological activities and their effectiveness was highly increased from short to long N-alkyl chains. DoGPA exhibited more potent biological activity against all target strains than other N-alkyl glucosylamines tested. Using a radial growth method, we demonstrated that this compound completely inhibited fungal growth at 0.5 x 10(-4) mol mL(-1), while OcGPA and HeGPA lead to 71% and 43% fungal inhibition, respectively. Using the coating method, we demonstrated that DoGPA completely inhibited bacterial growth at 0.025 x 10(-4) and 0.05 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively, while at the same concentrations, OcGPA exhibited weaker antibacterial activity of 12% and 27%, respectively, for L. innocua and S. typhimurium. The hole plate method enabled us to estimate the minimum inhibitory concentration (MIC) of DoGPA found to be 0.02 x 10(-4) and 0.025 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively. Glucosylamines with N-hydroxyalkyl and short N-alkyl chains varying from C-2 to C-4 exhibited weaker antimicrobial activity.

  DOI：

  10.1021/jf9016114
• 作为产物：
  描述：

  可得然胶 、 辛胺 以 甲醇 为溶剂， 以60%的产率得到N-octyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Influence of the Variation of the Alkyl Chain Length ofN-Alkyl-β-d-glycosylamine Derivatives on Antifungal Properties

  摘要：

  Twelve new glucosidic and galactosidic derivatives of N-alkylaminosugars with different alkylamines from 6 to 18 carbons were synthesized and characterized by H-1 and C-13 NMR. Their antifungal activity against the food fungal pathogen Aspergillus niger was evaluated using the radial growth assay. The influence of the variation of the alkyl chain length of N-alkylaminosugars on the mycelium growth was then discussed. Inhibition by the different alkylamines is shown as a biostatic effect rather than a biocidal effect. It was observed that alkylamines keep their antifungal properties after a thermal treatment compatible with food packaging and processing.

  DOI：

  10.1021/jf3015798
• 作为试剂：
  描述：

  葡萄糖 、 辛胺 、 乙醇 在 N-octyl-β-D-glucopyranosylamine 作用下， 以 甲醇 为溶剂， 反应 2.33h， 生成 N-octyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Glycosylated particle of latex or of inorganic oxide and process for the

  摘要：

  本发明涉及一种具有表面功能基团的乳胶或无机氧化物的糖基化颗粒。至少一部分所述功能基团连接到糖基残基。颗粒物质优选由聚合乙烯类不饱和单体得到的聚合物或硅胶组成。本发明在生物学中作为检测试剂应用。

  公开号：

  US05814407A1

文献信息

• The aggregation behaviour of two structurally isomeric glycolipids
  作者：George S. Attard、Wesley P. Blackaby、Andrew R. Leach

  DOI：10.1016/0009-3084(94)90114-7

  日期：1994.10

  The two structurally isomeric glycolipids N-octyl-(1-hexadecylamido)-beta-D-glucopyranoside (Glc-N-[8/16]) and N-hexadecyl-(1-octylamido)-beta-D-glucopyranoside (Glc-N[16/8]) were synthesized. The lyotropic phase behaviour of these isomers was investigated in order to determine the extent to which the relative disposition of the alkyl chains with respect to the amide unit affects the aggregation properties

  两个结构异构的糖脂N-辛基-（1-十六烷基酰胺基）-β-D-吡喃葡萄糖苷（Glc-N- [8/16]）和N-十六烷基-（1-辛基酰胺基）-β-D-吡喃葡萄糖苷（Glc-合成了N 16/8。为了确定烷基链相对于酰胺单元的相对位置影响两亲物的聚集性质的程度，研究了这些异构体的溶致相行为。两种异构体均显示出层状和逆拓扑立方中间相。相对于Glc-N- [16/8]异构体，非层状相的程度和多态性在Glc-N- [8/16]异构体中似乎更明显。为了使这种行为合理化，进行了分子力学研究。
• Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta
  作者：Théoneste Muhizi、Véronique Coma、Stéphane Grelier

  DOI：10.1016/j.carres.2008.07.005

  日期：2008.9

  Various glucosylamines were synthesized from glucose and different alkyl amine compounds. These amino compounds are P-D-glucopyranosylamine (GPA), N-ethyl-beta-D-glucopyranosylamine (EtGPA), N-butyl-beta-D-glucopyranosylamine (BuGPA), N-hexyl-beta-D-glucopyranosylamine (HeGPA), N-octyl-beta-D-glucopyranosylamine (OcGPA), N-dodecyl-beta-D-glucopyranosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucopyranosylamine (HEtGPA) and N,N-di(2-hydroxyethyl)-beta-D-glucopyranosylamine (DHEtGPA). They were tested for their antifungal activity against the growth of Coriolus versicolor and Poria placenta. An improvement of the antifungal activity with the increase of alkyl chain length was observed. DoGPA exhibited the best antifungal activity against both strains. It completely inhibited the fungal growth at 0.01 x 10(-3) mol mL(-1) and 0.0075 x 10-3 Mol mL(-1) for C. versicolor and P. placenta, respectively. For other glucosylamines higher concentrations were needed for complete inhibition of fungi. (C) 2008 Elsevier Ltd. All rights reserved.
• Particule de latex ou d'oxyde minéral glycosylée, procédé de préparation d'une telle particule et utilisation de celle-ci en tant qu'agent de détection biologique ou de chromatographie d'affinité
  申请人：MERCK EUROLAB S.A.

  公开号：EP0709402B1

  公开（公告）日：2002-06-26
• US5814407A
  申请人：——

  公开号：US5814407A

  公开（公告）日：1998-09-29
• [EN] PHOSPHATIDYLCHOLINE SYNTHESIS INHIBITORS<br/>[FR] INHIBITEURS DE LA SYNTHESE DE LA PHOSPHATIDYLCHOLINE
  申请人：——

  公开号：WO1998009668A2

  公开（公告）日：1998-03-12

  [EN] Use of an amphiphilic compound in the manufacture of a medicament for the inhibition of phosphatidylcholine synthesis, said amphiphilic compound have the following properties: i) the compound copmprises a non-ionic, cationic or anionic hydrophilic head group and a hydrophobic tail group; ii) the head group has a cross section A and the tail group has a cross section B such that the ratio B:A is less than 0.7:1; iii) the tail group comprises a straight hydrocarbon chain having from 8 to 18 carbon atoms; and iv) the amphiphilic compound has a membrane/water partition coefficient of more than 1 x 10<-3>.
  [FR] L'invention porte sur l'utilisation d'un composé amphiphile pour la fabrication d'un médicament inhibant la synthèse de la phosphatidylcholine. Ledit composé amphiphile présente les propriétés suivantes: (i) il comporte un groupe hydrophile de tête non ionique, cationique ou anionique, et un groupe hydrophobe de queue, (ii) le groupe de tête présente une section A et le groupe de queue présente une section B telles que le rapport B:A est inférieur à 0,7:1, (iii) le groupe de queue comporte une chaîne droite d'hydrocarbures présentant de 8 à 18 atomes de carbone, et (iv) le composé amphiphile présente un coefficient de séparation membrane/eau supérieur à 1 x 10<-3>.