Synthesis of Tyrocidine A and Its Analogues by Spontaneous Cyclization in Aqueous Solution
- 30 July 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (17) , 2893-2895
- https://doi.org/10.1021/ol0263191
Abstract
Head-to-tail cyclization of peptides is a multistep process involving tedious C-terminal activation and side chain protection. Here we report a facile, quantitative cyclization method in aqueous ammonia solution for the total syntheses of the cyclic decapeptide antibiotic Tyrocidine A and its analogues from their fully deprotected linear thioester precursors on a solid support. This novel aqueous method is conformation-dependent and may be applicable to syntheses of other natural cyclic peptides.Keywords
This publication has 19 references indexed in Scilit:
- A Repertoire of Novel Antibacterial Diastereomeric Peptides with Selective Cytolytic ActivityJournal of Biological Chemistry, 1997
- Hydrophobicity, hydrophobic moment and angle subtended by charged residues modulate antibacterial and haemolytic activity of amphipathic helical peptidesFEBS Letters, 1997
- Selective Lysis of Bacteria but Not Mammalian Cells by Diastereomers of Melittin: Structure−Function StudyBiochemistry, 1997
- Peptide antibioticsThe Lancet, 1997
- Diastereomers of Cytolysins, a Novel Class of Potent Antibacterial PeptidesJournal of Biological Chemistry, 1996
- Peptide Helicity and Membrane Surface Charge Modulate the Balance of Electrostatic and Hydrophobic Interactions with Lipid Bilayers and Biological MembranesBiochemistry, 1996
- Reviving the antibiotic miracle?Science, 1994
- Design of model amphipathic peptides having potent antimicrobial activitiesBiochemistry, 1992
- Determination of individual side-chain conformations, tertiary conformations, and molecular topography of tyrocidine A from scalar coupling constants and chemical shiftsBiochemistry, 1979
- Appendix 2—Possible molecular models for gramicidin S and their relationship to present ideas of protein structureBiochemical Journal, 1957