6-O-<2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<<(R)-3-hydroxytetradecanoyl>amino>-β-D-glucopyranosyl>-2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<<(R)-3-hydroxytetradecanoyl>amino>α-D-glucopyranosyl phosphate | 90365-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-<2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<<(R)-3-hydroxytetradecanoyl>amino>-β-D-glucopyranosyl>-2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<<(R)-3-hydroxytetradecanoyl>amino>α-D-glucopyranosyl phosphate
• 英文别名: 2-deoxy-6-O-<2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-α-D-glucopyranose 1-phosphate；6-O-{2-deoxy-3-O-((R)-3-hydroxytetradecanoyl)-2-[((R)-3-hydroxytetradecanoyl)amino]-β-D-glucopyranosyl}-2-deoxy-3-O-((R)-3-hydroxytetradecanoyl)-2-[((R)-3-hydroxytetradecanoyl)amino]α-D-glucopyranosyl phosphate；lipid A-disaccharide-1-phosphate；[(2R,3R,4R,5S,6R)-5-hydroxy-2-[[(2R,3S,4R,5R,6R)-3-hydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxy-6-phosphonooxyoxan-2-yl]methoxy]-6-(hydroxymethyl)-3-[[(3R)-3-hydroxytetradecanoyl]amino]oxan-4-yl] (3R)-3-hydroxytetradecanoate
• CAS: 90365-28-9
• 化学式: C₆₈H₁₂₉N₂O₂₀P
• 分子量: 1325.75
• InChiKey: HLDJGHAAKRKPAV-QDORLFPLSA-N

物化性质

• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  91
• 可旋转键数：
  60
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  347
• 氢给体数：
  11
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  6-O-<2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<<(R)-3-hydroxytetradecanoyl>amino>-β-D-glucopyranosyl>-2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<<(R)-3-hydroxytetradecanoyl>amino>α-D-glucopyranosyl phosphate 生成 [(2S,3R,4R,5S,6R)-2,5-dihydroxy-6-[[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxyoxan-2-yl]oxymethyl]-3-[[(3R)-3-hydroxytetradecanoyl]amino]oxan-4-yl] (3R)-3-hydroxytetradecanoate
  参考文献：
  名称：

  磷酸化的四酰基二糖的化学合成，对应于脂质A的生物合成前体

  摘要：

  共合成2,2'-N; 描述了3,3'-O-四quis [（R）-3-羟基十四烷酰基]-β（1-6）-D-葡糖胺二糖1,4'-二磷酸酯。这是脂质A基本结构的首次确认，因为合成化合物显示出天然内毒素的大多数特征性生物活性。

  DOI：

  10.1016/s0040-4039(01)81258-2
• 作为产物：
  描述：

  在 钯 氢气 作用下， 生成 6-O-<2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<<(R)-3-hydroxytetradecanoyl>amino>-β-D-glucopyranosyl>-2-deoxy-3-O-<(R)-3-hydroxytetradecanoyl>-2-<<(R)-3-hydroxytetradecanoyl>amino>α-D-glucopyranosyl phosphate
  参考文献：
  名称：

  磷酸化的四酰基二糖的化学合成，对应于脂质A的生物合成前体

  摘要：

  共合成2,2'-N; 描述了3,3'-O-四quis [（R）-3-羟基十四烷酰基]-β（1-6）-D-葡糖胺二糖1,4'-二磷酸酯。这是脂质A基本结构的首次确认，因为合成化合物显示出天然内毒素的大多数特征性生物活性。

  DOI：

  10.1016/s0040-4039(01)81258-2

文献信息

• An Alternative Route for UDP-Diacylglucosamine Hydrolysis in Bacterial Lipid A Biosynthesis
  作者：Louis E. Metzger、Christian R. H. Raetz

  DOI：10.1021/bi1008744

  日期：2010.8.10

  The outer leaflet of the outer membranes of Gram-negative bacteria is composed primarily of lipid A, the hydrophobic anchor of lipopolysaccharide. Like Escherichia coli, most Gram-negative bacteria encode one copy of each of the nine genes required for lipid A biosynthesis. An important exception exists in the case of the fourth enzyme, LpxH, a peripheral membrane protein that hydrolyzes UDP-2,3-diacylglucosamine to form 2,3-diacylglucosamine 1-phosphate and UMP by catalyzing the attack of water at the alpha-P atom. Many Gram-negative organisms, including all alpha-proteobacteria and diverse environmental isolates, lack LpxH. Here, we report a distinct UDP-2,3-diacylglucosamine pyrophosphatase, designated LpxI, which has no sequence similarity to LpxH but generates the same products by a different route. LpxI was identified because its structural gene is located between lpxA and lpxB in Caulobacter crescentus. The lpxI gene rescues the conditional lethality of lpxH-deficient E. coli. Lysates of E. coli in which C. crescentus LpxI (CcLpxI) is overexpressed display high levels of UDP-2,3-diacylglucosamine pyrophosphatase activity. CcLpxI was purified to >90% homogeneity. CcLpxI is stimulated by divalent cations and is inhibited by EDTA. Unlike E. coli LpxH, CcLpxI is not inhibited by an increase in the concentration of detergent, and its pH dependency is different. When the CcLpxI reaction is conducted in the presence of (H2O)-O-18, the O-18 is incorporated exclusively into the 2,3-diacylglucosamine I-phosphate product, as judged by mass spectrometry, demonstrating that CcLpxI catalyzes the attack of water on the beta-P atom of UDP-2,3-diacylglucosamine.
• Enzymic synthesis and comparative biological evaluation of a phosphonate analog of the lipid A precursor
  作者：Dieter Scholz、Karl Bednarik、Gerald Ehn、Wolfgang Neruda、Evelyne Janzek、Hans Loibner、Karin Briner、Andrea Vasella

  DOI：10.1021/jm00089a019

  日期：1992.5

  Phosphonate analogue 5 of the lipid A precursor 4 has been prepared from phosphonate 2 and nucleotide 3 with the help of lipid AT synthase, isolated from the overproducing Escherichia coli mutant MC 1061 (DELTA-2512) or JB1104 (DELTA-2514). The biological properties of phosphonate 5 and phosphate 4 are quite similar to each other as compared in the limulus amoebocyte lysate assay, by the activation of the RAW264 murine macrophagelike cell line (determined by stimulation of ornithine decarboxylase), and by the pyrogenicity in rabbits. Hydrolytic removal of the 1-phosphate group of 4 is thus not a prerequisite for its biological activity.
• Chemical Synthesis of a Biosynthetic Precursor of Lipid A with a Phosphorylated Tetraacyl Disaccharide Structure
  作者：Masahiro Imoto、Hiroyuki Yoshimura、Michiharu Yamamoto、Tetsuo Shimamoto、Shoichi Kusumoto、Tetsuo Shiba

  DOI：10.1246/bcsj.60.2197

  日期：1987.6

  2,2′-N:3,3′-O-Tetrakis[(R)-3-hydroxytetradecanoyl]-β(1-6)-D-glucosamine disaccharide 1,4′-bis(phosphate) and its dephospho derivatives were synthesized. The bisphosphate prepared was shown to be identical with a natural biosynthetic precursor of lipid A which corresponds to the lipophilic part of lipopolysaccharide (LPS) in bacterial cell wall. The synthetic bis- and monophosphates exhibited many of

  2,2'-N:3,3'-O-Tetrakis[(R)-3-羟基十四烷酰基]-β(1-6)-D-葡糖胺二糖 1,4'-双(磷酸)及其脱磷衍生物合成的。制备的二磷酸盐显示与脂质 A 的天然生物合成前体相同，脂质 A 对应于细菌细胞壁中脂多糖 (LPS) 的亲脂部分。合成的双磷酸盐和单磷酸盐表现出 LPS 的许多典型内毒活性。因此，这项工作建立了脂质 A 生物合成前体的化学结构，并阐明了表达这些活性所需的基本结构。
• Chemical synthesis of phosphorylated tetraacyl disaccharide corresponding to a biosynthetic precursor of lipid A
  作者：M. Imoto、H. Yoshimura、M. Yamamoto、T. Shimamoto、S. Kusumoto、T. Shiba

  DOI：10.1016/s0040-4039(01)81258-2

  日期：1984.1

  A total synthesis of 2,2′-N; 3,3′-O-tetraquis[(R)-3-hydroxytetradecanoyl]-β(1–6)-D-glucosamine disaccharide 1,4′-diphosphate is described. This is the first confirmation of the fundamental structure of lipid A since the synthetic compound exhibited most of the characteristic biological activities of natural endotoxin.

  共合成2,2'-N; 描述了3,3'-O-四quis [（R）-3-羟基十四烷酰基]-β（1-6）-D-葡糖胺二糖1,4'-二磷酸酯。这是脂质A基本结构的首次确认，因为合成化合物显示出天然内毒素的大多数特征性生物活性。