Lipoyl-GMP
IUPAC 名称
{[(2R,3S,4R,5R)-5-{2-[5-(1,2-dithiolan-3-yl)pentanamido]-6-oxo-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
描述
Lipoyl-GMP is an intermediate in lipoic acid metabolism.In mammals, the posttranslational modification of unlipoylated apoproteins by addition of lipoic acid is done in a two-step enzymatic reaction using free lipoic acid. The free lipoic acid in the cell is first activated by reacting it
with adenosine triphosphate, using up two high energy phosphate bonds to form lipoyl-AMP (GMP), a process catalyzed by lipoate activating enzyme (LAE).41 The activated lipoyl moiety is subsequently used to form an amide bond with lysine residues of the unlipoylated apoprotein, which is catalyzed by lipoyl-AMP(GMP):N-lysine lipoyl transferase Interestingly, purified LAE from bovine liver mitochondria preferentially utilizes guanosine triphosphate, instead of adenosine triphosphate, for the activation of lipoic acid to form lipoyl-GMP.44 Furthermore, genetic analysis of LAE reveals that the enzyme is identical to
xenobiotic-metabolizing/medium-chain fatty acid:CoA ligase-III (XL-III) (also from bovine liver mitochondria). 44 Hence, there appear to be two pathways in which LAE is capable of activating carboxylic acids: one that uses guanosine triphosphate to form acyl-GMP; the other is dependent on adenosine triphosphate for the activation of carboxylic acids to the CoA thioester (acyl-CoA) via an
acyl-AMP intermediate [HMDB]
异构
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(NC(=O)CCCCC1CCSS1)NC2=O
InChI标识符
InChI=1S/C18H26N5O9PS2/c24-11(4-2-1-3-9-5-6-34-35-9)20-18-21-15-12(16(27)22-18)19-8-23(15)17-14(26)13(25)10(32-17)7-31-33(28,29)30/h8-10,13-14,17,25-26H,1-7H2,(H2,28,29,30)(H2,20,21,22,24,27)/t9?,10-,13-,14-,17-/m1/s1
键
DVZGUOFXTLKZTJ-LQLSJNDNSA-N