Synthesis of 1,2,3‐Triazole Analogues of Lincomycin |
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Authors: | Marie‐Pierre Collin Sven N Hobbie Erik C Böttger Andrea Vasella |
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Institution: | 1. Laboratorium für Organische Chemie, Department Chemie und Angewandte Biowissenschaften, ETH‐Zürich, HCI H?nggerberg, Wolfgang‐Pauli‐Strasse 10, CH‐8093 Zürich;2. Institut für Medizinische Mikrobiologie, Universit?t Zürich, Gloriastrasse 30/32, CH‐8006 Zürich |
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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 ‘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. |
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Keywords: | Lincomycin ‘ Click chemistry’ Mycobacterium smegmatis Antibiotics 1 2 3‐Triazoles X‐Ray crystallography |
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