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Total synthesis and assignment of the side chain stereochemistry of LI-F04a: an antimicrobial cyclic depsipeptide.
- Source :
-
Organic letters [Org Lett] 2010 Aug 06; Vol. 12 (15), pp. 3394-7. - Publication Year :
- 2010
-
Abstract
- The total synthesis of the potent antifungal and antibiotic cyclic depsipeptide LI-F04a and its side chain epimer was accomplished using macrolactonization to assemble the cyclic peptide core, followed by attachment of the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain. The side chain was assembled by Yamaguchi-Hirao alkylation of both enantiomers of a chiral epoxide to provide a pair of enantiomeric side chains. The attachment of both these chains to the cyclic peptide allowed the absolute configuration of the side chain hydroxyl group in LI-F04a to be assigned as (R).
- Subjects :
- Anti-Infective Agents chemistry
Antifungal Agents chemistry
Bacterial Proteins chemistry
Depsipeptides chemistry
Molecular Structure
Stereoisomerism
Anti-Infective Agents chemical synthesis
Anti-Infective Agents pharmacology
Antifungal Agents chemical synthesis
Antifungal Agents pharmacology
Bacillus chemistry
Bacterial Proteins chemical synthesis
Bacterial Proteins pharmacology
Depsipeptides chemical synthesis
Depsipeptides pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 12
- Issue :
- 15
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 20608662
- Full Text :
- https://doi.org/10.1021/ol101254m