Synthesis of lipopeptides using hydrazone chemical ligation.
In this paper we report that a hydrazinopeptide synthesized using solid-phase N-electrophilic amination with N-Boc-3-(4-cyanophenyl)oxaziridine reacted with a lipophilic peptide aldehyde to give the corresponding hydrazone plus an unexpected 1,3,4-oxadiazolidinopeptide containing two peptide aldehyde units. This methodology allows the synthesis of large lipopeptides.
Melnyk
O
O
Biomolécules associé au CNRS, URA 1309, Institut Pasteur de Lille/Institut de Biologie de Lille, France. oleg.melnyk@pasteur-lille.fr
Bossus
M
M
David
D
D
Rommens
C
C
Gras-Masse
H
H
D000586:Amination; D000595:Amino Acid Sequence; D002625:Chemistry, Organic / Q000379:methods; D006835:Hydrazones / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008074:Lipoproteins / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D006835:Hydrazones; D008074:Lipoproteins