rdf:type |
|
lifeskim:mentions |
umls-concept:C0002482,
umls-concept:C0002505,
umls-concept:C0003232,
umls-concept:C0061633,
umls-concept:C0075804,
umls-concept:C0205103,
umls-concept:C0205225,
umls-concept:C0205314,
umls-concept:C0220781,
umls-concept:C0233656,
umls-concept:C0598405,
umls-concept:C0679622,
umls-concept:C1883254
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pubmed:issue |
25
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pubmed:dateCreated |
2002-12-6
|
pubmed:abstractText |
Nocathiacin I (1) and nocathiacin IV (2) are novel indole-containing thiazolyl peptide antibiotics, which exhibit potent activity against key Gram-positive bacterial pathogens, including multi drug-resistant Staphylococcus aureus, Streptococcus pneumoniae, and Enterococcus faecium. New nocathiacins 7-12 were prepared from 2 by a condensation with glycolaldehyde followed by tandem reductive amination of the 2-oxoethyl intermediate 4. The latter was formed via Amadori rearrangement from initial 2-hydroxyethylideneamide 3. This transformation readily tolerates the complex architecture of nocathiacins and allows selective incorporation of water solubilizing groups to the primary amide in 2 without protecting group manipulation.
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pubmed:language |
eng
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pubmed:journal |
|
pubmed:citationSubset |
IM
|
pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Acetaldehyde,
http://linkedlifedata.com/resource/pubmed/chemical/Amides,
http://linkedlifedata.com/resource/pubmed/chemical/Anti-Bacterial Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Peptides,
http://linkedlifedata.com/resource/pubmed/chemical/Peptides, Cyclic,
http://linkedlifedata.com/resource/pubmed/chemical/Thiazoles,
http://linkedlifedata.com/resource/pubmed/chemical/Water,
http://linkedlifedata.com/resource/pubmed/chemical/glycolaldehyde,
http://linkedlifedata.com/resource/pubmed/chemical/nocathiacin I,
http://linkedlifedata.com/resource/pubmed/chemical/nocathiacin IV
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pubmed:status |
MEDLINE
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pubmed:month |
Dec
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pubmed:issn |
0022-3263
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pubmed:author |
|
pubmed:issnType |
Print
|
pubmed:day |
13
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pubmed:volume |
67
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pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
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pubmed:pagination |
8789-93
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pubmed:dateRevised |
2005-11-17
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pubmed:meshHeading |
pubmed-meshheading:12467390-Acetaldehyde,
pubmed-meshheading:12467390-Amides,
pubmed-meshheading:12467390-Anti-Bacterial Agents,
pubmed-meshheading:12467390-Catalysis,
pubmed-meshheading:12467390-Combinatorial Chemistry Techniques,
pubmed-meshheading:12467390-Drug Resistance, Multiple, Bacterial,
pubmed-meshheading:12467390-Enterococcus faecium,
pubmed-meshheading:12467390-Microbial Sensitivity Tests,
pubmed-meshheading:12467390-Molecular Structure,
pubmed-meshheading:12467390-Peptides,
pubmed-meshheading:12467390-Peptides, Cyclic,
pubmed-meshheading:12467390-Staphylococcus aureus,
pubmed-meshheading:12467390-Streptococcus pneumoniae,
pubmed-meshheading:12467390-Structure-Activity Relationship,
pubmed-meshheading:12467390-Thiazoles,
pubmed-meshheading:12467390-Water
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pubmed:year |
2002
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pubmed:articleTitle |
Synthesis of novel nocathiacin-class antibiotics. Condensation of glycolaldehyde with primary amides and tandem reductive amination of amadori-rearranged 2-oxoethyl intermediates.
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pubmed:affiliation |
Bristol-Myers Squibb Co., Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA.
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pubmed:publicationType |
Journal Article
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