Virginiae butanolide A (VB A) (3) is one of the virginiamycin-inducing factors from Streptomyces virginiae and has a unique 2,3-disubstituted butanolide skeleton which is common to other signal molecules in Streptomyces. The biosynthesis of 3 in Streptomyces antibioticus, a high producer of 3, was studied by experiments with labeled precursors. ¹³C and ²H NMR results as well as CI-MS analyses of dibenzoate samples indicated that the probable biosynthetic pathway to 3 involved coupling between a β-keto acid derivative and a C₃ unit from glycerol, such as dihydroxyacetone or a derivative.
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Sakuda et al. (1992) studied this question.