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Functionalization of protected tyrosine via Sonogashira reaction: synthesis of 3-(1,2,3-triazolyl)-tyrosine

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Abstract

1,2,3-Triazol tyrosines were synthesized from tyrosine alkynes that were in turn prepared via Sonogashira cross-coupling reaction. The tyrosine alkynes were subjected to click-chemistry reaction conditions leading to the corresponding 3-(1,2,3-triazolyl)-tyrosines in yields ranging from moderate to good.

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Acknowledgments

The authors gratefully acknowledge financial support from the São Paulo Research Foundation (FAPESP—Grant 2012/00424-2 and fellowship 2013/17960-7 to S.N.S.V.) and the National Council for Scientific and Technological Development (CNPq) for a fellowship (308.320/2010–7 to HAS).

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Authors and Affiliations

  1. Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brasil

    Stanley N. S. Vasconcelos, Bakhat Ali & Hélio A. Stefani

  2. Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brasil

    Anwar Shamim

  3. Centro de Engenharia e Ciências Exatas, Universidade Estadual do Oeste do Paraná, Toledo, PR, Brasil

    Isadora M. de Oliveira

Authors
  1. Stanley N. S. Vasconcelos
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  2. Anwar Shamim
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  3. Bakhat Ali
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  4. Isadora M. de Oliveira
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  5. Hélio A. Stefani
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Corresponding author

Correspondence to Hélio A. Stefani.

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Vasconcelos, S.N.S., Shamim, A., Ali, B. et al. Functionalization of protected tyrosine via Sonogashira reaction: synthesis of 3-(1,2,3-triazolyl)-tyrosine. Mol Divers 20, 469–481 (2016). https://doi.org/10.1007/s11030-015-9642-y

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  • DOI: https://doi.org/10.1007/s11030-015-9642-y

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