Biomimetic formation of gramicidin S by dimerization-cyclization of pentapeptide precursor on solid support |
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Authors: | Makoto Tamaki Kenji Honda Sho Kikuchi Rie Ishii |
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Affiliation: | Department of Chemistry, Faculty of Science, Toho University, Miyama, Funabashi, Chiba 274-8510, Japan |
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Abstract: | The biomimetic formation of gramicidin S, cyclo(-d-Phe-Pro-Val-Orn-Leu-)2, by the dimerization and cyclization of pentapeptide precursor without the protection of δ-amino group of the Orn residue was examined on a solid support. The cyclization of H-d-Phe-Pro-Val-Orn-Leu-oxime on a resin with an oxime group of 0.62 mmol/g in 1,4-dioxane directly gave gramicidin S in a 50% yield. The dimerization-cyclization mode on the solid support was similar to that of the biosynthesis of gramicidin S on an enzyme. |
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Keywords: | Gramicidin S Biomimetic synthesis Dimerization-cyclization on solid phase Oxime resin Reaction mechanism |
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