Synthesis of the mitogenic S-[2,3-bis(palmitoyloxy)propyl]-N-palmitoylpentapeptide from Escherichia coli lipoprotein.
The N-terminal pentapeptide of the lipoprotein from the outer membrane of Escherichia coli was obtained by coupling S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-N-palmitoyl-(R)-cysteine to O-tert-butylseryl-O-tert-butyl-seryl-asparaginyl-alanine tert-butyl ester followed by deprotection with trifluoroacetic acid. The tetrapeptide was built up from alanine tert-butyl ester with N-9-fluorenylmethyloxycarbonyl protected amino acids. S-[2,3-Bis(palmitoyloxy)propyl]-N-palmitoylcysteine was obtained from N,N'-dipalmitoylcystine di-tert-butyl ester via reduction to the thiol, and S-alkylation with racemic 3-bromo-1,2-propanediol followed by esterification with palmitic acid in the presence of dicyclohexylcarbodiimide/dimethylaminopyridine and deprotection with trifluoroacetic acid. The compounds were characterized unequivocally by 13C-NMR and mass spectra. The diastereomers of S-[2,3-bis(palmitoyloxy)propyl]-N-palmitoylcysteine tert-butyl ester with opposite configuration at the propyl-C-2 atom could be separated on a silica-gel column.
D004926:Escherichia coli / Q000032:analysis*; D055666:Lipopeptides; D008074:Lipoproteins / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D008934:Mitogens / Q000138:chemical synthesis*; D009842:Oligopeptides / Q000138:chemical synthesis*
D055666:Lipopeptides; D008074:Lipoproteins; D008934:Mitogens; D009842:Oligopeptides; C038293:2,3-bis(palmitoyloxy)-2-propyl-N-palmitoyl-cysteinyl-seryl-seryl-asparaginyl-alanine