Document Detail


Decarbonylative approach to the synthesis of enamides from amino acids: stereoselective synthesis of the (Z)-aminovinyl-D-cysteine unit of mersacidin.
MedLine Citation:
PMID:  22296268     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The Pd- and Ni-promoted decarbonylation of amino acid thioesters proceeds smoothly to yield enamides. The synthesis of the (S)-(Z)-AviMeCys subunit of mersacidin, an MRSA-active lantibiotic, via this approach, is described.
Authors:
Pablo García-Reynaga; Angela K Carrillo; Michael S VanNieuwenhze
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2012-02-01
Journal Detail:
Title:  Organic letters     Volume:  14     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Feb 
Date Detail:
Created Date:  2012-02-20     Completed Date:  2012-05-15     Revised Date:  2013-06-26    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1030-3     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47505, USA.
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MeSH Terms
Descriptor/Qualifier:
Amides / chemistry*
Amino Acid Sequence
Amino Acids / chemistry*
Bacteriocins / chemistry*
Cysteine / chemistry
Molecular Sequence Data
Nickel / chemistry
Palladium / chemistry
Peptides / chemistry*
Protein Carbonylation
Stereoisomerism
Vinyl Compounds / chemical synthesis*
Grant Support
ID/Acronym/Agency:
AI 059327/AI/NIAID NIH HHS; R01 AI059327-06/AI/NIAID NIH HHS
Chemical
Reg. No./Substance:
0/Amides; 0/Amino Acids; 0/Bacteriocins; 0/Peptides; 0/Vinyl Compounds; 128104-18-7/mersacidin; 52-90-4/Cysteine; 7440-02-0/Nickel; 7440-05-3/Palladium
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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