A practical synthesis of gramicidin s and sugar amino Acid containing analogues.
A practical gram-scale and high-yielding synthesis of the antimicrobial peptide gramicidin S is presented. An Fmoc-based solid-phase peptide synthesis protocol is employed for the generation of the linear decapeptide precursor, which is cyclized in solution to afford the target compound. The versatility of our method is demonstrated by the construction of eight gramicidin S analogues (15a-h) having nonproteinogenic sugar amino acid residues (4-7) incorporated in the turn regions.
Grotenbreg
Gijsbert M
GM
Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Kronemeijer
Martijn
M
Timmer
Mattie S M
MS
El Oualid
Farid
F
van Well
Renate M
RM
Verdoes
Martijn
M
Spalburg
Emile
E
van Hooft
Peter A V
PA
de Neeling
Albert J
AJ
Noort
Daan
D
van Boom
Jacques H
JH
van der Marel
Gijsbert A
GA
Overkleeft
Herman S
HS
Overhand
Mark
M
D000596:Amino Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001409:Bacillus cereus / Q000187:drug effects; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000494:pharmacology; D013293:Enterococcus faecalis / Q000187:drug effects; D004912:Erythrocytes / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D006096:Gramicidin / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D008826:Microbial Sensitivity Tests; D013210:Staphylococcus / Q000187:drug effects
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D002241:Carbohydrates; D006096:Gramicidin