rdf:type |
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lifeskim:mentions |
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pubmed:issue |
14
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pubmed:dateCreated |
2004-6-18
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pubmed:abstractText |
Recently we described the structures of two new bromotyrosine-derived alkaloids that inhibit the detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis. Here we describe a concise total synthesis of bromotyrosine oxime 1. The six-step synthesis of 1 utilized a trifluoromethyloxazole intermediate, whose hydrolysis product underwent alkylation and coupling to agmatine to give the inhibitor in approximately 40% overall yield. Oxime 1 inhibited MCA and its homolog AcGI deacetylase with IC(50) values of 30 and 150 microM, respectively.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Amidohydrolases,
http://linkedlifedata.com/resource/pubmed/chemical/Anti-Infective Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Bacterial Proteins,
http://linkedlifedata.com/resource/pubmed/chemical/Hydrocarbons, Fluorinated,
http://linkedlifedata.com/resource/pubmed/chemical/N-acetyl-1-D-inosityl-2-amino-2-deox...,
http://linkedlifedata.com/resource/pubmed/chemical/Oxazoles,
http://linkedlifedata.com/resource/pubmed/chemical/Oximes,
http://linkedlifedata.com/resource/pubmed/chemical/Tyrosine,
http://linkedlifedata.com/resource/pubmed/chemical/bromotyrosine,
http://linkedlifedata.com/resource/pubmed/chemical/mycothiol S-conjugate amidase
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pubmed:status |
MEDLINE
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pubmed:month |
Jul
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pubmed:issn |
0960-894X
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
16
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pubmed:volume |
14
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
3785-8
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:15203162-Alkylation,
pubmed-meshheading:15203162-Amidohydrolases,
pubmed-meshheading:15203162-Anti-Infective Agents,
pubmed-meshheading:15203162-Bacterial Proteins,
pubmed-meshheading:15203162-Hydrocarbons, Fluorinated,
pubmed-meshheading:15203162-Hydrolysis,
pubmed-meshheading:15203162-Inhibitory Concentration 50,
pubmed-meshheading:15203162-Kinetics,
pubmed-meshheading:15203162-Mycobacterium tuberculosis,
pubmed-meshheading:15203162-Oxazoles,
pubmed-meshheading:15203162-Oximes,
pubmed-meshheading:15203162-Structure-Activity Relationship,
pubmed-meshheading:15203162-Tyrosine
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pubmed:year |
2004
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pubmed:articleTitle |
Synthesis of a bromotyrosine-derived natural product inhibitor of mycothiol-S-conjugate amidase.
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pubmed:affiliation |
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892-0820, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
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