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Amino Acids

, Volume 46, Issue 10, pp 2325–2332 | Cite as

Thiophenyl-substituted triazolyl-thione l-alanine: asymmetric synthesis, aggregation and biological properties

  • Ashot S. Saghyan
  • Hayarpi M. Simonyan
  • Satenik G. Petrosyan
  • Arpine V. Geolchanyan
  • Giovanni N. RovielloEmail author
  • Domenica Musumeci
  • Valentina Roviello
Original Article

Abstract

In this work, we report the asymmetric synthesis and characterization of an artificial amino acid based on triazolyl-thione l-alanine, which was modified with a thiophenyl-substituted moiety, as well as in vitro studies of its nucleic acid-binding ability. We found, by dynamic light scattering studies, that the synthetic amino acid was able to form supramolecular aggregates having a hydrodynamic diameter higher than 200 nm. Furthermore, we demonstrated, by UV and CD experiments, that the heteroaromatic amino acid, whose enzymatic stability was demonstrated by HPLC analysis also after 24 h of incubation in human serum, was able to bind a RNA complex, which is a feature of biomedical interest in view of innovative antiviral strategies based on modulation of RNA–RNA molecular recognition.

Keywords

Artificial amino acid RNA CD Light scattering 

Notes

Acknowledgments

The authors would like to thank Dr. Leopoldo Zona for his invaluable assistance. We are also grateful to the institutions that supported our laboratory (Consiglio Nazionale delle Ricerche and Yerevan State University).

Conflict of interest

The authors state that there is no conflict of interests.

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Copyright information

© Springer-Verlag Wien 2014

Authors and Affiliations

  • Ashot S. Saghyan
    • 1
  • Hayarpi M. Simonyan
    • 1
  • Satenik G. Petrosyan
    • 1
  • Arpine V. Geolchanyan
    • 1
  • Giovanni N. Roviello
    • 2
    Email author
  • Domenica Musumeci
    • 3
  • Valentina Roviello
    • 4
  1. 1.Department of Pharmaceutical ChemistryYerevan State UniversityYerevanArmenia
  2. 2.Istituto di Biostrutture E Bioimmagini, CNRNaplesItaly
  3. 3.Dipartimento di Scienze ChimicheUniversità di Napoli “Federico II”NaplesItaly
  4. 4.Istituto Per L’Ambiente Marino Costiero, CNRCalata Porta di MassaNaplesItaly

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