Anaerobic degradation of lysine: IV. Cobamide coenzyme-dependent migration of an amino group from carbon 6 of β-lysine (3,6-diaminohexanoate) to carbon 5 forming a new naturally occurring amino acid, 3,5-diaminohexanoate

Abstract

Methods are described for the accumulation and detection of 3,5-diaminohexanoate, a new basic amino acid intermediate in the lysine fermentation pathway formed by the reaction sequence α-lysine ⇌ β-lysine ⇌ 3,5-diaminohexanoate. Migration of the terminal amino group of β-lysine to carbon atom 5 in a cobamide coenzyme-dependent reaction results in the formation of 3,5-diaminohexanoate. The dihydrochloride, and the N,N′-dibenzoyl derivative and the δ-lactam (4-amino-6-methyl-2-piperidone) of the new amino acid were prepared and characterized chemically and by infrared and nuclear magnetic resonance spectral analyses. The new amino acid is fermented by crude extracts of Clostridium sticklandii and Clostridium M-E to the same fatty acids that are produced from α- and β-lysine.