1-O-octyl-α-D-glucopyranosiduronic acid | 156967-55-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-O-octyl-α-D-glucopyranosiduronic acid
• 英文别名: octyl α-D-glucopyranosiduronic acid；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-octoxyoxane-2-carboxylic acid
• CAS: 156967-55-4
• 化学式: C₁₄H₂₆O₇
• 分子量: 306.356
• InChiKey: SYLNWYZPTDDGMH-HNRZYHPDSA-N

物化性质

• 沸点：
  497.6±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-octyl-α-D-glucopyranosiduronic acid 、 guanosine 5'-diphospho-D-mannose 在 magnesium chloride 作用下， 以 水 为溶剂， 反应 2.0h， 生成 octyl α-D-mannopyranosyl-(1→4)-α-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria

  摘要：

  Glucuronosyl diacylglycerides (GlcAGroAc(2)) are functionally important glycolipids and membrane anchors for cell wall lipoglycans in the Corynebacteria. Here we describe the complete synthesis of distinct acyl-isoforms of GlcAGroAc(2) bearing both acylation patterns of (R)-tuberculostearic acid (C-19:0) and palmitic acid (C-16:0) and their mass spectral characterization. Collision-induced fragmentation mass spectrometry identified characteristic fragment ions that were used to develop "rules" allowing the assignment of the acylation pattern as C-19:0 (sn-1), C-16:0 (sn-2) in the natural product from Mycobacterium smegmatis, and the structural assignment of related C-18:1 (sn-1), C-16:0 (sn-2) GlcAGroAc(2) glycolipids from M. smegmatis and Corynebacterium glutamicum. A synthetic hydrophobic octyl glucuronoside was used to characterize the GDP-mannose-dependent mannosyltransferase MgtA from C. g/utamicum that extends GlcAGroAc(2). This enzyme is an Mg2+/Mn2+-dependent metalloenzyme that undergoes dramatic activation upon reduction with dithiothreitol.

  DOI：

  10.1021/jo302508e
• 作为产物：
  描述：

  正辛基 α-D-葡萄糖苷 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 phosphate buffer 、 乙腈 为溶剂， 反应 96.0h， 以89%的产率得到1-O-octyl-α-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Synthesis of sugar-based chelating surfactants for metal removal from wastewater

  摘要：

  Four chelating surfactants were synthesized in a few steps from octyl D-glucosides. Their main interfacial properties were determined, and their flotation properties were evaluated on a laboratory scale using Fe(III) as a model contaminant metal. The performance on metal extraction was mainly dependent on the complexing functional group, but the surfactant efficiency was also important. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.015

文献信息

• Oxidation of methyl and n-octyl α-d-glucopyranoside over graphite-supported platinum catalysts: effect of the alkyl substituent on activity and selectivity
  作者：Johannes H Vleeming、Ben F.M Kuster、Guy B Marin

  DOI：10.1016/s0008-6215(97)00157-2

  日期：1997.9

  catalyst was investigated. An increase of the length of the n-alkyl substituent from methyl to n-octyl resulted in a ten-fold decrease of the catalyst activity and an increase of the selectivity at pH 8.0 and 323 K. The selectivity decreased with increasing pH. The lower activity for a longer n-alkyl substituent is attributed to steric effects upon adsorption on the platinum surface and not to internal diffusion

  研究了在载有石墨的铂催化剂上用分子氧将甲基和正辛基Ol-D-吡喃葡萄糖苷氧化为甲基和正辛基Ce-D-glu-吡喃二葡萄糖苷。正烷基取代基的长度从甲基增加到正辛基导致催化剂活性降低十倍，并且在pH 8.0和323 K下的选择性增加。随着pH的增加，选择性降低。对于更长的正烷基取代基的较低活性归因于在铂表面上吸附时的空间效应，而不是由于内部扩散限制。提出了一个暂定的反应方案，该方案描述了通过仲羟基的氧化，环裂解和水解形成副产物的方法。主要副产品是具有2，4，4，4的一元羧酸盐和二元羧酸盐。烷基取代基的氧化产生6个碳原子和一元羧酸酯。CC-键裂解主要发生在2和C-3或C-4和C-5之间，前者对于较长的烷基取代基不太重要。对较长烷基取代基的较高选择性归因于其对水解的保护能力以及相邻羟基向铂表面的暴露。©1997爱思唯尔科学有限公司。
• Boelrijk, Alexandra E. M.; Dorst; Reedijk, Jan, Recueil des Travaux Chimiques des Pays-Bas, 1996, vol. 115, # 11-12, p. 536 - 541
  作者：Boelrijk, Alexandra E. M.、Dorst、Reedijk, Jan

  DOI：——

  日期：——
• 10.1002/recl.19941130907
  作者：Boelrijk, Alexandra E. M.、Reedijk, Jan

  DOI：10.1002/recl.19941130907

  日期：——
• Synthesis of sugar-based chelating surfactants for metal removal from wastewater
  作者：Nadège Ferlin、Diego Grassi、Carlos Ojeda、Mariano J.L. Castro、Eric Grand、Alicia Fernández Cirelli、José Kovensky

  DOI：10.1016/j.carres.2008.01.015

  日期：2008.4

  Four chelating surfactants were synthesized in a few steps from octyl D-glucosides. Their main interfacial properties were determined, and their flotation properties were evaluated on a laboratory scale using Fe(III) as a model contaminant metal. The performance on metal extraction was mainly dependent on the complexing functional group, but the surfactant efficiency was also important. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria
  作者：Benjamin Cao、Xingqiang Chen、Yoshiki Yamaryo-Botte、Mark B. Richardson、Kirstee L. Martin、George N. Khairallah、Thusita W.T. Rupasinghe、Roisin M. O’Flaherty、Richard A.J. O’Hair、Julie E. Ralton、Paul K. Crellin、Ross L. Coppel、Malcolm J. McConville、Spencer J. Williams

  DOI：10.1021/jo302508e

  日期：2013.3.15

  Glucuronosyl diacylglycerides (GlcAGroAc(2)) are functionally important glycolipids and membrane anchors for cell wall lipoglycans in the Corynebacteria. Here we describe the complete synthesis of distinct acyl-isoforms of GlcAGroAc(2) bearing both acylation patterns of (R)-tuberculostearic acid (C-19:0) and palmitic acid (C-16:0) and their mass spectral characterization. Collision-induced fragmentation mass spectrometry identified characteristic fragment ions that were used to develop "rules" allowing the assignment of the acylation pattern as C-19:0 (sn-1), C-16:0 (sn-2) in the natural product from Mycobacterium smegmatis, and the structural assignment of related C-18:1 (sn-1), C-16:0 (sn-2) GlcAGroAc(2) glycolipids from M. smegmatis and Corynebacterium glutamicum. A synthetic hydrophobic octyl glucuronoside was used to characterize the GDP-mannose-dependent mannosyltransferase MgtA from C. g/utamicum that extends GlcAGroAc(2). This enzyme is an Mg2+/Mn2+-dependent metalloenzyme that undergoes dramatic activation upon reduction with dithiothreitol.