Total synthesis and absolute configuration of the antibiotic oligopeptide (4S)-(+)-anthelvencin A and its 4R-(-) enantiomer

The total syntheses of the two enantiomers of anthelvencin A (the naturally occurring isomer (4S)-(+)-1a and its enantiomer (4R)-(-)-1b) with enantiomeric excess of 80 plus or minus 4% are described. The absolute configuration of natural anthelvencin A is thereby unambiguously assigned. The two enan...

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Bibliographic Details
Published in:Journal of organic chemistry 1988-04, Vol.53 (9), p.1855-1859
Main Authors: Lee, Moses, Coulter, Diane M, Lown, J. William
Format: Article
Language:English
Subjects:
anthelvencin A
Chemistry
Exact sciences and technology
Organic chemistry
peptide antibiotics
Peptides
Preparations and properties
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Summary:The total syntheses of the two enantiomers of anthelvencin A (the naturally occurring isomer (4S)-(+)-1a and its enantiomer (4R)-(-)-1b) with enantiomeric excess of 80 plus or minus 4% are described. The absolute configuration of natural anthelvencin A is thereby unambiguously assigned. The two enantiomers, (+)-1a and (-)-1b, bind to duplex calf thymus DNA with constants of (1.46 plus or minus 0.01) x 10 super(7) and (1.35 plus or minus 0.01) x 10 super(7) M super(-1), respectively, as determined by an ethidium displacement assay.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00244a003