Unpublished Paper
Synthesis of two tripeptide intermediates of linear hexapeptide fragment of teixobactin.docx
(2017)
Abstract
Pathogenic bacteria have become increasingly resistant to current antibiotics employed today to treat bacterial infections. While antimicrobial resistance increasingly threatens global health, the development of therapeutic agents with novel mechanisms of actions increases in demand. A recently discovered 11-amino acid depsipeptide known as teixobactin has exhibited potent antimicrobial activity against pathogenic bacteria. The pathogens subjected to teixobactin were not able to develop resistivity to the antimicrobial peptide. In this research, the synthesis of two tripeptide fragments of the linear hexapeptide fragment of teixobactin, Boc-D-Gln-D-allo-Ile-Ile-OR and Boc-N(Me)-D-Phe-Ile-Ser(OBn)-OBn were developed. HATU mediated peptide-coupling, benzylation, and EDCI/DMAP mediated esterification steps were employed in the synthesis. The final products were characterized and confirmed utilizing 1H-NMR, 13C-NMR, and mass spectrometry.Pathogenic bacteria have become increasingly resistant to current antibiotics employed today to treat bacterial infections. While antimicrobial resistance increasingly threatens global health, the development of therapeutic agents with novel mechanisms of actions increases in demand. A recently discovered 11-amino acid depsipeptide known as teixobactin has exhibited potent antimicrobial activity against pathogenic bacteria. The pathogens subjected to teixobactin were not able to develop resistivity to the antimicrobial peptide. In this research, the synthesis of two tripeptide fragments of the linear hexapeptide fragment of teixobactin, Boc-D-Gln-D-allo-Ile-Ile-OR and Boc-N(Me)-D-Phe-Ile-Ser(OBn)-OBn were developed. HATU mediated peptide-coupling, benzylation, and EDCI/DMAP mediated esterification steps were employed in the synthesis. The final products were characterized and confirmed utilizing 1H-NMR, 13C-NMR, and mass spectrometry.
Keywords
- Teixobactin
Disciplines
Publication Date
Spring May 1, 2017
Citation Information
Edward Ramos. "Synthesis of two tripeptide intermediates of linear hexapeptide fragment of teixobactin.docx" (2017) Available at: http://works.bepress.com/edward-ramos/1/