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Synthesis of 1,2,3-triazole analogues of lincomycin


Collin, M P; Hobbie, S N; Böttger, E C; Vasella, A (2008). Synthesis of 1,2,3-triazole analogues of lincomycin. Helvetica Chimica Acta, 91(10):1838-1848.

Abstract

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 9click 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.

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 9click 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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:04 Faculty of Medicine > Institute of Medical Microbiology
Dewey Decimal Classification:570 Life sciences; biology
610 Medicine & health
Language:English
Date:2008
Deposited On:03 Feb 2009 09:44
Last Modified:05 Apr 2016 12:56
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Publisher DOI:10.1002/hlca.200890196
Permanent URL: http://doi.org/10.5167/uzh-12295

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