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Synthesis of 1,2,3‐Triazole Analogues of Lincomycin
Author(s) -
Collin MariePierre,
Hobbie Sven N.,
Böttger Erik C.,
Vasella Andrea
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890196
Subject(s) - chemistry , moiety , alkyne , triazole , azide , aryl , structural isomer , ring (chemistry) , amide , lincomycin , stereochemistry , alkyl , mutant , click chemistry , triazine , combinatorial chemistry , organic chemistry , antibiotics , biochemistry , catalysis , gene
In search for new antibiotics we replaced the amide moiety of lincomycin 1 by a 1,2,3‐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.