Biomimetic stereoselective formation of methyllanthionine.
Fmoc-(2R,3S)-3-methyl-Se-phenylselenocysteine was used for the synthesis of dehydrobutyrine (Dhb)-containing peptides. Biomimetic cyclization via Michael addition of Cys to a Dhb yielded the B-ring of the lantibiotic subtilin as a single diastereomer. The methyllanthionine product was shown to have the natural configuration by preparation of the authentic stereoisomer. The formation of a single isomer suggests that the prepeptide has a strong intrinsic preference for the stereochemistry observed in lantibiotics. [reaction: see text]
Zhou
Hao
H
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801, USA.
van der Donk
Wilfred A
WA
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D005449:Fluorenes; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013440:Sulfides
C411453:2,7-di-tert-butyl-9-fluorenylmethoxycarbonyl chloride; D000900:Anti-Bacterial Agents; D005449:Fluorenes; D007202:Indicators and Reagents; D013440:Sulfides; C005080:beta-methyllanthionine; D000409:Alanine