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Optimization of Coupling Methods for the Introduction of Mono-Benzyl Phosphate Esters of Fmoc Protected Phosphoamino Acids

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Peptides: The Wave of the Future

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

Abstract

Mono-benzyl phosphate esters of Fmoc protected phosphoamino acids, Fmoc-Aaa(PO(OBzl)OH)-OH (Aaa = Ser, Thr, Tyr), are extremely valuable tools for the synthesis of phosphopeptides by Fmoc SPPS methods [1]. However, a recent report [2] has indicated that the use of standard activation methods with these derivatives can lead to poor yields. In this poster, the development of an optimized coupling protocol and its application in the synthesis of multiphosphorylated peptides is described.

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References

  1. Wakamiya, T., Saruta, K., Yasuoka, J., Kusumoto, S. Chem. Lett. 1099 (1994); White, P., Beythien, J., In Epton, R. (Ed.) Innovations & Perspectives in Solid Phase Synthesis & Combinatorial Libraries, 4th International Symposium, Mayflower Scientific Ltd., Birmingham, 1996, p. 557.

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  2. Perich, J., Ede, N., Eagle, S., Bray, A. Lett Peptide Sci. 6, 91 (1999).

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  3. Pascal, R., Schmit, P.-O., Mendre, C., Dufour, M.-N., Guillon, G., In Martinez, J. and Fehrentz, J.-A. (Eds) Peptides 2000, Proc. 26th European Peptide Symposium, Éditions EDK, Paris, 2001, p. 263.

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© 2001 Springer Science+Business Media Dordrecht

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White, P. (2001). Optimization of Coupling Methods for the Introduction of Mono-Benzyl Phosphate Esters of Fmoc Protected Phosphoamino Acids. 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_42

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  • DOI: https://doi.org/10.1007/978-94-010-0464-0_42

  • 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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