期刊
ORGANIC LETTERS
卷 4, 期 8, 页码 1335-1338出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol025629g
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资金
- NIGMS NIH HHS [GM 58822] Funding Source: Medline
[GRAPHICS] Fmoc-(2R,3S)-3-methyl-Se-phenylselenocysteine was used for the synthesis of dehydrobutyrine (Dhb)-containing peptides. Blomimetic 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.
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