Reversed approach to S-farnesylation and S-palmitoylation: application to an efficient synthesis of the C-terminus of lipidated human N-ras hexapeptide

Kandasamy Pachamuthu; Xiangming Zhu; Richard R Schmidt

doi:10.1021/jo0482357

Reversed approach to S-farnesylation and S-palmitoylation: application to an efficient synthesis of the C-terminus of lipidated human N-ras hexapeptide

J Org Chem. 2005 Apr 29;70(9):3720-3. doi: 10.1021/jo0482357.

Authors

Kandasamy Pachamuthu¹, Xiangming Zhu, Richard R Schmidt

Affiliation

¹ Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.

PMID: 15845014
DOI: 10.1021/jo0482357

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
Catalysis
Humans
Indicators and Reagents
Lipoproteins / chemical synthesis*
Lipoproteins / chemistry
Molecular Structure
Palmitates / chemical synthesis*
Palmitates / chemistry
Peptide Fragments / chemical synthesis*
Peptide Fragments / chemistry
Protein Prenylation*
Sulfhydryl Compounds / chemistry
ras Proteins / chemical synthesis*
ras Proteins / chemistry

Substances

Indicators and Reagents
Lipoproteins
Palmitates
Peptide Fragments
Sulfhydryl Compounds
ras Proteins