Synthesis of anabasine-6′-carboxylic acid from aldosine, the aldol crosslinking amino acid of elastin

Abstract

A novel pyridine compound, 6-(3-pyridyl)pipecolinic acid 2, was synthesized by treatment, with Fe³⁺/ activated charcoal, of aldosine 1 which was the acid hydrolysis product of the aldol crosslink moiety 3 of elastin. Structural identification was performed by spectroscopic analysis. Compound 2 was named anabasine-6′-carboxylic acid, because it is the 6′-carboxylic acid derivative of anabasine, which is an alkaloid of (among others) the tobacco plant. Anabasine-6′-carboxylic acid might be an oxidative decarboxylation product of aldosine.