Ring-closing alkyne metathesis approach toward the synthesis of alkyne mimics of thioether A-, B-, C-, and DE-ring systems of the lantibiotic nisin Z.
[reaction: see text] Ring-closing alkyne metathesis toward the synthesis of the alkyne-brigded A-, B-, C-, and (D)E-ring mimics of the peptide antibiotic nisin Z is described. We have successfully synthesized alkyne-bridged cyclic peptides containing 4-7 amino acid residues in yields ranging from 18 to 82%.
Department of Medicinal Chemistry, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, The Netherlands.
Nourdin
N
Ghalit
Alex J
AJ
Poot
Alois
A
Fürstner
Dirk T S
DT
Rijkers
Rob M J
RM
Liskamp
D000480:Alkynes / Q000737:chemistry*; D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009561:Nisin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D000900:Anti-Bacterial Agents; D010456:Peptides, Cyclic; D009561:Nisin; C071364:nisin Z