Self-radiation induced exchange between tritiated water and organic compounds. The labelling of L-chiro-inositol, myo-inositol and Hexa-O-methyl-L-chiro-inositol

Abstract

The stereochemistry of the tritiation of L-chiro-inositol, myo-inositol and hexa-O-methyl-L-chiro-inositol by self-radiation induced exchange with tritiated water of high specific activity has been investigated. Predominance of configurational retention was found to accompany tritium labelling in the two inositols, while substantial configurational inversion occurred in the hexa-O-methyl derivative. Tritiation occurred predominantly at C 1 in L-chiro-inositol, with slight inversion at this position alone accompanying the labelling. Comparison with Wilzbach T₂ gas exposure results indicates the HTO method yields less by-products, myo-inositol having a radiochemical purity of 97%.