Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-21095
Collin, M P; Hobbie, S N; Böttger, E C; Vasella, A (2009). Synthesis and Evaluation of S- and C(1)-Substituted Analogues of Lincomycin. Helvetica Chimica Acta, 92(2):230-266.
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New thioglycosides and C(1)-alkylated thioglycosides (S-ulosides) of lincomycin were synthesized, and their antibiotic activities were determined. The S-aryl and S-arylalkyl analogues 11a – 11i were obtained by S-glycosylation of the sulfoxides 7 with arenethiols, or by S-alkylation of the thiol 14 with alkyl bromides. Lincomycin derivatives 27, 32a, 32b, 38a, 38b, 44, and 47 were prepared via Henry reaction or Michael addition of the lincosamine-derived 1-deoxy-1-nitropyranoses 22. The S-alkyl derivatives showed a similar activity and specificity as lincomycin. Lipophilic S-uloside analogues were two- to fourfold less active than the parent antibiotic, whilst the hydrophilic analogues were inactive.
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|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
|Deposited On:||06 Oct 2009 07:30|
|Last Modified:||23 Nov 2012 14:23|
|Publisher:||Verlag Helvetica Chimica Acta|
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