Synthesis of microcin SF608.
The first total synthesis of aquatic peptide microcin SF608 is described. Coupling of L-Hpla with the dipeptide L-Phe-L-Choi followed by coupling with agmatine and a deprotection step gave microcin SF608. In addition, the levorotatory character of L-Hpla (5) was thoroughly established, and the conformational analysis of L-Choi containing peptides 1 and 8-10 was performed using NMR spectroscopy to examine the cis-trans isomer equilibrium of the L-Phe-L-Choi amide bond.
Valls
Nativitat
N
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.
Vallribera
Mercè
M
López-Canet
Meritxell
M
Bonjoch
Josep
J
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001430:Bacteriocins / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides; D013237:Stereoisomerism; D014361:Trypsin Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D001430:Bacteriocins; D007211:Indoles; D010455:Peptides; D014361:Trypsin Inhibitors; C419325:aeruginosin 298-A; C436761:aeruginosin 298-B; C470082:microcin SF608; C020411:microcin; D007930:Leucine