benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate | 1421868-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate
• 英文别名: benzyl (2S,3S,4S,5R,6S)-6-[(2S)-3-[tert-butyl(diphenyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]propoxy]-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
• CAS: 1421868-60-1
• 化学式: C₆₁H₆₆O₁₀Si
• 分子量: 987.275
• InChiKey: NCBFRTMNKHGMMG-DWVZRMITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  72
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 在 4-二甲氨基吡啶 、 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 氟化氢吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate
  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：

  1,6-二-O-乙酰基-2,3,4-三-O-苄基-beta-D-吡喃葡萄糖 在 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘代三甲硅烷 、 碘苯二乙酸 、 sodium methylate 、 四丁基碘化铵 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 2,4,6-三叔丁基嘧啶 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 150.0h， 生成 benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate
  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

• 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.