Biomimetic formation of gramicidin S by dimerization–cyclization of pentapeptide precursor on solid support

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...

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Bibliographic Details
Published in:Tetrahedron letters 2006-11, Vol.47 (48), p.8475-8478
Main Authors: Tamaki, Makoto, Honda, Kenji, Kikuchi, Sho, Ishii, Rie
Format: Article
Language:English
Subjects:
Biomimetic synthesis
Dimerization–cyclization on solid phase
Gramicidin S
Oxime resin
Reaction mechanism
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Summary: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 50%. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.09.146