Synthesis of l-Octaarginine through Microencapsulated Palladium-Catalyzed Allyl Ester Deprotection

Ana M. Pérez-López; Dávir González-Calderón; Antonio Occorso; Javier Galindo-Ángel; José F. Domínguez-Seglar; Juan A. Tamayo; Mónica Díaz-Gavilán; José A. Gómez-Vidal

doi:10.1055/s-0034-1378379

Synlett, Table of Contents

Synlett 2014; 25(16): 2319-2322
DOI: 10.1055/s-0034-1378379

letter

Synthesis of l-Octaarginine through Microencapsulated Palladium-Catalyzed Allyl Ester Deprotection

Ana M. Pérez-López

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus de Cartuja s/n, 18071 Granada, Spain Fax: +34(958)243845 Email: jagvidal@ugr.es

,

Dávir González-Calderón

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus de Cartuja s/n, 18071 Granada, Spain Fax: +34(958)243845 Email: jagvidal@ugr.es

,

Antonio Occorso

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus de Cartuja s/n, 18071 Granada, Spain Fax: +34(958)243845 Email: jagvidal@ugr.es

,

Javier Galindo-Ángel

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus de Cartuja s/n, 18071 Granada, Spain Fax: +34(958)243845 Email: jagvidal@ugr.es

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José F. Domínguez-Seglar

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus de Cartuja s/n, 18071 Granada, Spain Fax: +34(958)243845 Email: jagvidal@ugr.es

,

Juan A. Tamayo

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus de Cartuja s/n, 18071 Granada, Spain Fax: +34(958)243845 Email: jagvidal@ugr.es

,

Mónica Díaz-Gavilán

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus de Cartuja s/n, 18071 Granada, Spain Fax: +34(958)243845 Email: jagvidal@ugr.es

,

José A. Gómez-Vidal*

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus de Cartuja s/n, 18071 Granada, Spain Fax: +34(958)243845 Email: jagvidal@ugr.es

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Abstract

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Abstract

Octaarginine has been described as a molecular transporter. We report a useful synthesis of orthogonally protected l-octaarginine by using a method based on a microencapsulated palladium catalyst. Known palladium-based methods for allyl ester deprotection have been modified to facilitate purification of the unprotected intermediates. This improvement in the purification step has also been tested with a variety of allyl α-amino esters and allyl α,β-unsaturated esters.

Key words

peptides - palladium - protecting groups - esters

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References

References and Notes

For reports on l-Arg homopolymers as molecular carriers for cellular uptake, see:

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