IUPAC 名称
(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid
描述
Geranylgeranylcysteine is a modified thioether amino acid in which an isoprenyl group (geranylgeranyl) has been attached to the sulfhydryl group of cysteine through a thioether bond. Geranylgeranylcysteine is typically formed through posttranslational (prenylation) protein modification whereupon degradation of the parent protein leaves the modified (prenylated) amino acid. Prenylation is a relatively recently discovered post-translational modification of proteins that directs cytosollic proteins to membranes while at the same time activating them functionally. The change in hydrophobicity that is essential for membrane binding is done via the covalent attachment of a polyisoprene (such as a farnesyl or geranylgeranyl group) to a C-terminal cysteine by a thioether bond. Prenylated proteins can comprise up to 2% of total cellular protein. Prenylcysteine lyase is an enzyme that is capable of cleaving the thiother bond in prenylcysteines and is used to help in the turnover of prenylated proteins. Prenylcysteine lyase deficiency leads to the accumulation of farnesylcysteine and geranylgeranylcysteine in brain and liver. (PMID: 9287348) [HMDB]
InChI标识符
InChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1