Preparation and purification of [14C] labeled N-demethyl lincomycin and propylproline from [14C] tyrosine

Propylproline and N-demethyl-lincomycin, two intermediates in lincomycin biosynthesis, were prepared in radiolabeled form. [14C]-labeled N-demethyl-lincomycin was synthesized by a resting cell suspension of a lincomycin negative mutant of Streptomyces lincolnensis that was fed methylthiolincosaminide and uniformly labeled [14C]-tyrosine. [14C]-N-demethyl-lincomycin was isolated from the culture medium by ion exchange chromatography and reverse phase-ion pair high pressure liquid chromatography. [14C]-propylproline was generated by the base hydrolysis of [14C]-N-demethyl-lincomycin and isolated by anion exchange chromatography. The products had radiochemical purities greater than 95% and specific activities of 5.9 mCi/mmole. (author)