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Facile Synthesis of a Constrained Dipeptide Unit (DPU) for Use as a β-Sheet Promoter

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Book cover Peptides: The Wave of the Future

Part of the book series: American Peptide Symposia ((APSY,volume 7))

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Abstract

Previously described syntheses of lactam-constrained dipeptide amino acids involve lengthy and expensive procedures to obtain an aldehyde intermediate 4 [1]. We report a general route from D-glutamic acid to lactam-dipeptide units. The target lactam-constrained amino acid has a six-membered ring back-bone and isopropyl and isobutyl side-chains (Figure 1). The overall synthesis is shown in Figure 2.

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References

  1. Moss, N., Beaulieu, P., Duceppe, J.-S., Ferland, J.-M., Gauthier, J., Ghiro, E., Goulet, S., Guse, I., Llinas-Bruntet, M., Plante, R., Plamondon, L., Wernic, D., Deziel, R. J. Med. Chem. 39, 2178 (1996).

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  2. Padron, J.M., Kokotos, G., Martin, T., Markidis, T., Gibbons, W.A., Martin, V.S. Tetrahedron: Assymmetry 9, 3381–3394 (1998).

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© 2001 Springer Science+Business Media Dordrecht

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Oguz, U., Gauthier, T.J., McLaughlin, M.L. (2001). Facile Synthesis of a Constrained Dipeptide Unit (DPU) for Use as a β-Sheet Promoter. In: Lebl, M., Houghten, R.A. (eds) Peptides: The Wave of the Future. American Peptide Symposia, vol 7. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-0464-0_17

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  • DOI: https://doi.org/10.1007/978-94-010-0464-0_17

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-3905-5

  • Online ISBN: 978-94-010-0464-0

  • eBook Packages: Springer Book Archive

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