Post-synthesis incorporation of a lipidic side chain into a peptide on solid support.
A new strategy for the synthesis of lipopeptides has been developed. Using Weinreb (N-methoxy, N-methyl) amide as an aldehyde function precursor on the side chains of Asp or Glu residues, this new strategy avoids the synthesis of a lipidic amino acid residue before its incorporation in the peptide sequence. The aldehyde generated on the solid support can react with ylides leading to unsaturated or saturated side chains or with various nucleophiles to yield non-coded amino acid residues incorporated into the sequence.
Douat
Céline
C
Laboratoire des Amino-acides, Peptides et Protéines, UMR 5810, Faculté de Pharmacie, Universités Montpellier I et II, 34093 Montpellier Cédex 5, France.
Heitz
Annie
A
Paris
Marielle
M
Martinez
Jean
J
Fehrentz
Jean-Alain
JA
D001559:Benzhydryl Compounds; D002855:Chromatography, Thin Layer; D008055:Lipids / Q000737:chemistry*; D008074:Lipoproteins / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011487:Protein Conformation; D012996:Solutions
C030545:4-methylbenzhydrylamine resin; D001559:Benzhydryl Compounds; D008055:Lipids; D008074:Lipoproteins; D010455:Peptides; D012996:Solutions