A growth factor (TJF) for a malo-lactic fermentation bacterium has been isolated from tomato juice, and found to be a β-glucoside. The NMR spectra of TJF and its acetate revealed that the glucosyl residue linked to the hydroxyl group at C-2' or C-4' of D- or L-pantothenic acid moiety. Then, 2'-O-(β-D-glucopyranosyl)-DL-pantothenic acid (I), 4'-O-(β-D-glucopyranosyl)-DL-pantothenic acid (II) and 4'-O-(β-D-glucopyranosyl)-D(R)-pantothenic acid (II-a) were synthesized, and II-a and 4'-O-(β-D-glucopyranosyl)-L-pantothenic acid (II-b) were obtained by the optical resolution of the acetate of II. Among the above compounds, II-a was identical with natural TJF regarding to the biological activity, NMR and ORD spectra, and thin-layer chromatography.
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Amachi et al. (1971) studied this question.