Reversed approach to S-farnesylation and S-palmitoylation: application to an efficient synthesis of the C-terminus of lipidated human N-ras hexapeptide.
[reaction: see text] A general reversed approach is described to synthesize S-palmitoylated and S-farnesylated peptides via S(N)2 displacement of bromide by reaction of a thiol group containing lipid as nucleophile with bromoalanine-containing peptides as electrophile. By employing this approach, lipidated peptides, including characteristic partial structures of human Ras peptides, were synthesized in good yields. This method gives access to farnesylated, palmitoylated, and doubly lipidated peptides.
Pachamuthu
Kandasamy
K
Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
Zhu
Xiangming
X
Schmidt
Richard R
RR
D000595:Amino Acid Sequence; D002384:Catalysis; D006801:Humans; D007202:Indicators and Reagents; D008074:Lipoproteins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010168:Palmitates / Q000138:chemical synthesis* / Q000737:chemistry; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry; D017368:Protein Prenylation; D013438:Sulfhydryl Compounds / Q000737:chemistry; D018631:ras Proteins / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D008074:Lipoproteins; D010168:Palmitates; D010446:Peptide Fragments; D013438:Sulfhydryl Compounds; D018631:ras Proteins