Synthesis of [d-Pyrenylalanine4,4′]gramicidin S by Solid-Phase-Synthesis and Cyclization-Cleavage Method with Oxime Resin
- 1 February 1992
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 21 (2) , 191-194
- https://doi.org/10.1246/cl.1992.191
Abstract
Cyclic decapeptide [D-pyrenylalanine4,4′]gramicidin S has been efficiently synthesized via stepwise solid-phase-synthesis and cyclization-cleavage with the Kaiser’s oxime resin in 45% total yield. This analog showed the similar conformation to the natural gramicidin S in MeOH. The pyrene ring introduced into the peptide is a useful fluorescent probe for the study of the mechanism of the antimicrobial activity.Keywords
This publication has 13 references indexed in Scilit:
- Evaluation of the oxime resin based segment synthesis-condensation approach using RNase T1 as a model synthetic targetThe Journal of Organic Chemistry, 1991
- Synthesis of tyrocidine a: Use of oxime resin for peptide chain assembly and cyclizationTetrahedron Letters, 1990
- A Chemically Synthesized Antennapedia Homeo Domain Binds to a Specific DNA SequenceScience, 1988
- Synthesis, receptor binding activity and fluorescence property of fluorescent enkephalin analogs containing L‐1‐pyrenylalanineInternational Journal of Peptide and Protein Research, 1987
- The use of polymer-bound oximes for the synthesis of large peptides usable in segment condensation: synthesis of a 44 amino acid amphiphilic peptide model of apolipoprotein A-1Journal of the American Chemical Society, 1985
- Synthesis of protected peptide segments and their assembly on a polymer-bound oxime: application to the synthesis of a peptide model for plasma apolipoprotein A-IThe Journal of Organic Chemistry, 1983
- Solid-phase synthesis of protected peptides on a polymer-bound oxime: preparation of segments comprising the sequence of a cytotoxic 26-peptide analogThe Journal of Organic Chemistry, 1982
- Polymer-bound oxime esters as supports for solid-phase peptide synthesis. The preparation of protected peptide fragmentsThe Journal of Organic Chemistry, 1980
- Carboxyl-catalyzed intramolecular aminolysis. Side reaction in solid-phase peptide synthesisJournal of the American Chemical Society, 1972
- Improved synthesis of gramicidin S via solidphase synthesis and cyclization by the azide methodJournal of the American Chemical Society, 1971