1-O-((R)-10-methylstearyl)-2-O-palmityl-sn-glyceryl α-D-glucopyranosiduronic acid | 1421868-69-0

• 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-((R)-10-methylstearyl)-2-O-palmityl-sn-glyceryl α-D-glucopyranosiduronic acid
• 英文别名: 3-alpha-D-glucuronosyl-2-palmitoyl-1-[(10R)-10-methyloctadecanoyl]-sn-glycerol；(2S,3S,4S,5R,6S)-6-[(2S)-2-hexadecanoyloxy-3-[(10R)-10-methyloctadecanoyl]oxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1421868-69-0
• 化学式: C₄₄H₈₂O₁₁
• 分子量: 787.128
• InChiKey: NLPJYNZQKGQLQQ-KZEZPSQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  55
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (R)-10-methyloctadecanoic acid 在 4-二甲氨基吡啶 、 ammonium cerium (IV) nitrate 、 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 20% palladium hydroxide-activated charcoal 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 76.33h， 生成 1-O-((R)-10-methylstearyl)-2-O-palmityl-sn-glyceryl 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

文献信息

• α-Glucuronosyl and α-glucosyl diacylglycerides, natural killer T cell-activating lipids from bacteria and fungi
  作者：Satvika Burugupalli、Catarina F. Almeida、Dylan G. M. Smith、Sayali Shah、Onisha Patel、Jamie Rossjohn、Adam P. Uldrich、Dale I. Godfrey、Spencer J. Williams

  DOI：10.1039/c9sc05248h

  日期：——

  Microbial α-glycosyl diacylglycerides when presented by the antigen presenting molecule CD1d are recognized by both classical type I and atypical Natural Killer T cell receptors.

  当微生物α-糖基二酰基甘油被抗原呈递分子CD1d呈现时，它们被经典的I型和非典型自然杀伤T细胞受体所识别。
• 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.