1,2-O-Dihexadecanoyl-1,2-hexadecandiol | 56599-97-4

• 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: 1,2-O-Dihexadecanoyl-1,2-hexadecandiol
• 英文别名: 2-Palmitoyloxypalmityl palmitate；2-hexadecanoyloxyhexadecyl hexadecanoate
• CAS: 56599-97-4
• 化学式: C₄₈H₉₄O₄
• 分子量: 735.272
• InChiKey: JBXHTKYUTHLVLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.9
• 重原子数：
  52
• 可旋转键数：
  46
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-十六烷二醇 、 hexadecanoyl CoA 生成 1,2-O-Dihexadecanoyl-1,2-hexadecandiol 、 coenzyme A
  参考文献：
  名称：

  The triacylglycerol synthesis enzyme DGAT1 also catalyzes the synthesis of diacylglycerols, waxes, and retinyl esters

  摘要：

  The final step of triacylglycerol biosynthesis is catalyzed by acyl CoA:diacylglycerol acyltransferase (DGAT) enzymes. The two known DGATs, DGAT1 and DGAT2, are encoded by unrelated genes. Although both DGAT1 and DGAT2 knockout mice have reduced tissue triacylglycerol contents, they have disparate phenotypes, prompting us to investigate whether the two enzymes have unrecognized functional differences. We now report that DGAT1 exhibits additional acyltransferase activities in vitro, including those of acyl CoA: monoacylglycerol acyltransferase (MGAT), wax monoester and wax diester synthases, and acyl CoA: retinol acyltransferase (ARAT), which catalyze the synthesis of diacylglycerols, wax esters, and retinyl esters, respectively. These activities were demonstrated in in vitro assays with membranes from insect cells or homogenates from COS7 cells overexpressing DGAT1. Wax synthase and ARAT activities were also demonstrated in intact COS7 cells expressing DGAT1. Additionally, cells and tissues from DGAT1-deficient mice exhibited reduced ARAT activity, and the mice had increased levels of unesterified retinol in their livers on a high-retinol diet. Our findings indicate that DGAT1 can utilize a variety of acyl acceptors as substrates in vitro and suggest that these activities may be relevant to the in vivo functions of DGAT1. - Yen, C-L. E., M. Monetti, B. J. Burri, and R. V. Farese, Jr. The triacylglycerol synthesis enzyme DGAT1 also catalyzes the synthesis of diacylglycerols, waxes, and retinyl esters.

  DOI：

  10.1194/jlr.m500036-jlr200

文献信息

• A human skin multifunctional O-acyltransferase that catalyzes the synthesis of acylglycerols, waxes, and retinyl esters
  作者：Chi-Liang Eric Yen、Charles H. Brown、Mara Monetti、Robert V. Farese

  DOI：10.1194/jlr.m500168-jlr200

  日期：2005.11

  Acyl-CoA-dependent O-acyltransferases catalyze reactions in which fatty acyl-CoAs are joined to acyl acceptors containing free hydroxyl groups to produce neutral lipids. In this report, we characterize a human multifunctional O-acyltransferase (designated MFAT) that belongs to the acyl-CoA: diacylglycerol acyltransferase 2/acyl-CoA: monoacylglycerol acyltransferase (MGAT) gene family and is highly expressed in the skin. Membranes of insect cells and homogenates of mammalian cells overexpressing MFAT exhibited significantly increased MGAT, acyl-CoA: fatty acyl alcohol acyltransferase (wax synthase), and acyl-CoA: retinol acyltransferase (ARAT) activities, which catalyze the synthesis of diacylglycerols, wax monoesters, and retinyl esters, respectively. Furthermore, when provided with the appropriate substrates, intact mammalian cells overexpressing MFAT accumulated more waxes and retinyl esters than control cells. We conclude that MFAT is a multifunctional acyltransferase that likely plays an important role in lipid metabolism in human skin.