| Synthesis of paromomycin derivatives modified at C(5'') to selectively target bacterial rRNA. | |
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MedLine Citation:
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PMID: 17049499 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The furanosyl moiety (ring III) of C(6')-deoxyparomomycin and paromomycin was modified in search of aminoglycoside antibiotics with altered selectivity. The key intermediates were the N-Boc-protected derivative of C(6')-deoxyparomomycin and the benzylidene-protected paromomycin. Their H(2)C(5'')-OH group was oxidised with trichlorocyanuric acid or [bis(acetoxy)iodo]benzene in the presence of catalytic amounts of TEMPO to yield the corresponding aldehydes and acids, which were transformed into the protected alkoxy imines, amides and the amine. Standard deprotection gave the title compounds derived from C(6')-deoxyparomomycin and derived from paromomycin that proved less active than paromomycin and its C(6')-deoxy analogue. |
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Authors:
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Iwona Kudyba; Déborah Perez Fernandez; Erik C Böttger; Andrea Vasella |
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Publication Detail:
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Type: Journal Article Date: 2006-10-17 |
Journal Detail:
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Title: Carbohydrate research Volume: 342 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 2007 Feb |
Date Detail:
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Created Date: 2007-02-02 Completed Date: 2007-04-13 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: Netherlands |
Other Details:
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Languages: eng Pagination: 499-519 Citation Subset: IM |
Affiliation:
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Laboratorium für Organische Chemie, ETH Zürich, HCI, CH-8093 Zürich, Switzerland. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Mycobacterium smegmatis
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drug effects Oxidation-Reduction Paromomycin / analogs & derivatives*, chemical synthesis*, pharmacology RNA, Bacterial / chemistry* RNA, Ribosomal / chemistry* Ribosomes / drug effects Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/RNA, Bacterial; 0/RNA, Ribosomal; 7542-37-2/Paromomycin |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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