Synthesis of an olefin-containing cyclic peptide using the solid-phase Horner–Emmons reaction

Linear and cyclic olefin-containing peptides were efficiently prepared by a combination of Dess–Martin oxidation and the Horner–Emmons reaction on a solid support. Linear and cyclic olefin peptides containing the substrate sequence for human T-cell leukemia virus type-1 (HTLV-1) were efficiently syn...

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Bibliographic Details
Published in:Tetrahedron letters 2004, Vol.45 (1), p.99-102
Main Authors: Bang, Jeong Kyu, Hasegawa, Koki, Kawakami, Toru, Aimoto, Saburo, Akaji, Kenichi
Format: Article
Language:English
Subjects:
Cyclic peptide
Horner–Emmons reaction
HTLV-1 protease
olefin peptide
Solid phase synthesis
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Summary:Linear and cyclic olefin-containing peptides were efficiently prepared by a combination of Dess–Martin oxidation and the Horner–Emmons reaction on a solid support. Linear and cyclic olefin peptides containing the substrate sequence for human T-cell leukemia virus type-1 (HTLV-1) were efficiently synthesized on a solid support using the Horner–Emmons reaction. The precursor peptide aldehyde was prepared by oxidation of the corresponding peptide alcohol with Dess–Martin periodinane. The oxidation reaction proceeded quantitatively on a cross-linked ethoxylate acrylate resin (CLEAR) support instead of a polystyrene-based support. Cyclization on the solid support was achieved via an amide bond formation mediated by EDC/HOAt to yield a single major product. The linear olefin peptide was cleaved by HTLV-1 protease at the scissile site, whereas the cyclic olefin peptide functions as a competitive inhibitor rather than a substrate.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.10.093