Feeding experiments with Streptomyces griseoflavus using deuterium‐labeled racemic 3,3‐[D2]‐ (6b), 4,4‐[D2]‐ (6c), 5,5‐[D2]‐ (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 γ‐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 ψ‐oxime analogue of 4‐hydroxylysine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
No takes yet. Share an insight, caveat, or question.
Brandl et al. (2004) studied this question.
Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context: