Synthesis of 1,2,3-Triazole Analogues of Lincomycin

In search for ne v antibiotics we replaced the amide moiety of lincomycin I by a 1,23-triazole ring. The 1.2,3-triazoles 10a-10k were obtained as single regioisomers by 'click reaction' of azide 5 with the alkyne 9k, derived from propyl hygric acid, and the alkyl, aryl, or cycloalkyl alkynes ribosomes 9a-9j. The new analogues proved inactive towards wild-type and A2058G mutant.