Teruo Amachi

A Growth Factor for Malo-lactic Fermentation Bacteria:Part II. Structure and Synthesis of a Novel Pantothenic Acid Derivative Isolated from Tomato Juice

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 Il-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.

[43] Syntheses of glycosyl derivatives of pantothenic acid and pantetheine

Publisher Summary This chapter discusses the syntheses of glycosyl derivatives of pantothenic acid and pantetheine. It is well known that wine maturation involves a bacterial conversion of malic acid to lactic acid, this process is designated as “malo-lactic fermentation” (MLF). MLF occurs following an alcoholic fermentation in wine making; it not only reduces the acidity of wine but also improves its quality. The growth factor has been isolated from tomato juice and named TJF; it is characterized as 4-O-(β-D-glucopyranosyl)-o-pantothenic acid. TJF can be substituted with a large amount (about 100 times) of D-pantothenic acid for its growth. D-Pantothenic acid is widely distributed in nature and well known to be a precursor of coenzyme A. The metabolism of pantothenic acid to coenzyme A in microorganisms is described in the chapter; the initial reaction is phosphorylation at the C-4 hydroxyl group of pantothenic acid.