First preparative biocatalytic hydrolysis and S-methylation of cyclic trithiocarbonates

The biocatalytic degradation of a cyclic trithiocarbonate, 6-amino-5-methoxycarbonyl-thieno[2,3-d]-1,3-dithiole-2-thione , is reported. The product of the hydrolysis of the five-membered ring by Pseudomonas chlororaphis ATCC 9447 oxidatively dimerized to form the tetrathiocin derivative . Furthermore, we performed the first preparative biocatalytic methylation of an unnatural compound employing Emericella unguis ATCC 10032 by cleaving the dithiole ring followed by methylation of both thiol groups to form the methylated product in 64% isolated yield.