Lincomycin (LCM)

Lincomycin is a lincosamide antibiotic that comes from the actinomyces Streptomyces lincolnensis. A related compound, clindamycin, is the 7-chloro-7-deoxy derivative synthesized by reacting lincomycin with thionyl chloride. Lincomycin is an antibiotic classified as a constituent of the lincosamide group, which typically feature a 6,8-dideoxy-6-aminooctose lincosamine. In Lincomycin A, this sugar moiety is linked via an amide bond to an amino acid derivative. Lincomycin biosynthesis occurs via a biphasic pathway. Propylproline and methylthiolincosamide are each synthesized separately, which are then condensed to form N-demethyllincomycin and finally methylated by S-adenosyl methionine to give lincomycin. In the biosynthesis of the amino acid moiety of lincomycin, tyrosine comprises seven of the nine carbons in the prophylhygric acid, while the remaining two carbons are added in reactions with S-adenosyl methionine.