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Total Synthesis of trans,trans-Sanguinamide B and Conformational Isomers
- Source :
- Organic Letters. 14:1198-1201
- Publication Year :
- 2012
- Publisher :
- American Chemical Society (ACS), 2012.
-
Abstract
- The first total synthesis of Sanguinamide B is reported, prepared via an efficient synthetic strategy. The natural product, trans,trans-Sanguinamide B (1), was generated in a thermodynamic ratio with trans,cis-Sanguinamide B (2) and cis,cis-Sanguinamide B (3). Complete conversion of the cis,cis-Sanguinamide B conformer (3) to the natural product (1) and the trans,cis- conformer (2) was achieved by heating to 170 °C. Biological evaluation indicated that the Sanguinamide B conformers disrupted the activity of a virulence determinant in P. aeruginosa.
- Subjects :
- Natural product
Molecular Structure
Virulence
Stereochemistry
Organic Chemistry
Total synthesis
Peptides, Cyclic
Biochemistry
Thiazoles
chemistry.chemical_compound
Isomerism
chemistry
Pseudomonas aeruginosa
Sanguinamide B
Physical and Theoretical Chemistry
Oxazoles
Conformational isomerism
Biological evaluation
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 14
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....c9262fc3ea506df71f4d0baeb5f02d47