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The biosynthesis of 3-(trans-2-nitrocyclopropyl)alanine, a constituent of the signal metabolite hormaomycin
Feeding experiments with Streptomyces griseoflavus using deuterium-labeled racemic 3,3-[D2]- (6b), 4,4-[D2]- (6c), 5,5-[D 2]- (6d), and 6,6-[D2]-lysine (6e), and 3-amino-5-(2-amino-1,1-dideuterioethyl)-4,5-dihydrofuran-2-one dihydrochloride (34¡¤2HCl) were carried out in order to obtain detailed information about the hitherto unknown biosynthetic pathway from lysine to the unusual amino acid 3-(trans-2?-nitrocyclopropyl)alanine [(3-Ncp)Ala] (2), which is a building block of hormaomycin 1a. The corresponding lysine dihydrochlorides were prepared in 33, 24, 19, and 30% overall yield, respectively, along a new efficient general synthetic route applying an alkylation of the lithium enolate of O’Donnel’s glycine equivalent 7 as a key step. In the attempted preparation of 5,5-[D2]-4-hydroxylysine (29), the respective gamma-lactone (34¡¤2 HCl) was obtained in five steps with 10% overall yield. The distribution of isotope labels in hormaomycins 1b-d led to the formulation of a reasonable cyclization mechanism of 2-amino-4-hydroxy-6-(hydroxyimino)hexanoic acid, an omega-oxime analogue of 4-hydroxylysine. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics