1,2-dihexadecanoyl-3-(9Z-hexadecenoyl)-sn-glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-dihexadecanoyl-3-(9Z-hexadecenoyl)-sn-glycerol
• 英文别名: [(2R)-2-hexadecanoyloxy-3-[(Z)-hexadec-9-enoyl]oxypropyl] hexadecanoate
• 化学式: C₅₁H₉₆O₆
• 分子量: 805.3
• InChiKey: FEKLSEFRUGWUOS-DLOIZKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21
• 重原子数：
  57
• 可旋转键数：
  49
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  palmitoleoyl-CoA(4-) 、 1,2-二棕榈酰-sn-丙三醇 生成 1,2-dihexadecanoyl-3-(9Z-hexadecenoyl)-sn-glycerol 、 coenzyme A
  参考文献：
  名称：

  The Mycobacterium tuberculosis Ag85A is a novel diacylglycerol acyltransferase involved in lipid body formation

  摘要：

  SummaryMycobacterium tuberculosis accumulates large amounts of triacylglycerol (TAG) which acts as storage compounds for energy and carbon. The mycobacterial triacylglycerols stored in the form of intracellular lipid droplets are essential for long‐term survival of M. tuberculosis during a dormant state. We report here that when the M. tuberculosis mycolytransferase Ag85A is overexpressed in Mycobacterium smegmatis mc2155, cell morphology was changed and the cells became grossly enlarged. A massive formation of lipid bodies and a change in lipid pattern was observed simultaneously. We suspected a possible role of Ag85A in the acyl lipid metabolism and discovered that the enzyme possesses acyl‐CoA:diacylglycerol acyltransferase (DGAT) activity in addition to its well‐known function as mycolyltransferase. Ag85A mediates the transesterification of diacylglycerol using long‐chain acyl‐CoA as acyl donors. The Km and Kcat values for palmitoleoyl‐coenzyme A were 390 µM and 55.54 min−1 respectively. A docking model suggests that palmitoleoyl‐coenzyme A and 1,2‐dipalmitin occupy the same active site as trehalose 6,6′‐dimycolate and trehalose 6′‐monomycolate. The site‐directed Ser126Ala mutation of the active site proved that this residue is involved in the catalytic activity of this enzyme. Although not proven conclusively for dormant stage of M. tuberculosis, our novel finding about the synthesis of TAGs by Ag85A strongly suggests that Ag85A may play a significant role in the formation of lipid storage bodies and thus also in the establishment and maintenance of a persistent tuberculosis infection.

  DOI：

  10.1111/j.1365-2958.2011.07792.x

文献信息

• The Mycobacterium tuberculosis Ag85A is a novel diacylglycerol acyltransferase involved in lipid body formation
  作者：Ayssar A. Elamin、Matthias Stehr、Ralf Spallek、Manfred Rohde、Mahavir Singh

  DOI：10.1111/j.1365-2958.2011.07792.x

  日期：2011.9

  SummaryMycobacterium tuberculosis accumulates large amounts of triacylglycerol (TAG) which acts as storage compounds for energy and carbon. The mycobacterial triacylglycerols stored in the form of intracellular lipid droplets are essential for long‐term survival of M. tuberculosis during a dormant state. We report here that when the M. tuberculosis mycolytransferase Ag85A is overexpressed in Mycobacterium smegmatis mc2155, cell morphology was changed and the cells became grossly enlarged. A massive formation of lipid bodies and a change in lipid pattern was observed simultaneously. We suspected a possible role of Ag85A in the acyl lipid metabolism and discovered that the enzyme possesses acyl‐CoA:diacylglycerol acyltransferase (DGAT) activity in addition to its well‐known function as mycolyltransferase. Ag85A mediates the transesterification of diacylglycerol using long‐chain acyl‐CoA as acyl donors. The Km and Kcat values for palmitoleoyl‐coenzyme A were 390 µM and 55.54 min−1 respectively. A docking model suggests that palmitoleoyl‐coenzyme A and 1,2‐dipalmitin occupy the same active site as trehalose 6,6′‐dimycolate and trehalose 6′‐monomycolate. The site‐directed Ser126Ala mutation of the active site proved that this residue is involved in the catalytic activity of this enzyme. Although not proven conclusively for dormant stage of M. tuberculosis, our novel finding about the synthesis of TAGs by Ag85A strongly suggests that Ag85A may play a significant role in the formation of lipid storage bodies and thus also in the establishment and maintenance of a persistent tuberculosis infection.