Scalable synthesis of orthogonally protected β-methyllanthionines by indium(III)-mediated ring opening of aziridines
Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g of β-methyllanthionine in a single batch.
Li, Ziran,Gentry, Zachary,Murphy, Brennan,Vannieuwenhze, Michael S.
Stereoselective syntheses of 4-oxa diaminopimelic acid and its protected derivatives via aziridine ring opening
Regio- and stereoselective aziridine ring opening with oxygen nucleophiles derived from serine and threonine provides a route to stereochemically pure 4-oxa-2,6-diaminopimelic acid (oxa-DAP) and its methyl-substituted derivatives. Oxa-DAP is a substrate of DAP epimerase, a key enzyme for biosynthesis of L-lysine and formation of peptidoglycan precursors. Orthogonally protected analogues of lanthionine and/β-methyllanthionine wherein oxygen replaces sulfur were prepared that could be used for solid-supported peptide synthesis to make oxa derivatives of lantibiotics.
Liu, Hongqiang,Pattabiraman, Vijaya R.,Vederas, John C.
p. 4211 - 4214
(2008/03/13)
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