Amino Acids

, Volume 51, Issue 4, pp 661–667 | Cite as

Synthesis of selenopeptides: an alternative way of incorporating selenocystine

  • Selvaraj Aravindhan
  • Harkesh B. SinghEmail author
  • Matthias Zeller
  • Ray J. Butcher
Original Article


Selenocysteine (Sec) residue cannot be directly attached to a peptide sequence unless the selenol form is protected beforehand and several problems have been reported in the preparation of Sec building blocks. In this article a series of selenocystine, the oxidized form of Sec, containing peptides has been synthesized using a new methodology, where Boc-NH-chloroalanine is coupled with methyl ester protected residues (Ala, Met, Phe) using DCC/HOBt as the coupling reagents providing di- and tripeptides. Further, the treatment of disodium diselenide with chloroalanine peptides (Boc-ClAla-Ala-OMe, Boc-ClAla-Met-OMe and Boc-ClAla-Ala-Phe-OMe) afforded the respective selenocystine-containing peptides (Boc-Sec-Ala-OMe, Boc-Sec-Met-OMe and Boc-Sec-Ala-Phe-OMe).


Disodium diselenide Selenopeptide Selenocysteine Selenocystine 



H. B. S. is grateful to the Department of Science and Technology, New Delhi, for a J. C. Bose Fellowship. A.S. gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for research fellowship. H. B. S. and S. A are thankful to Prof. M. Iwaoka for scientific discussion.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

726_2019_2698_MOESM1_ESM.docx (4.3 mb)
Supplementary material 1 (DOCX 4445 kb)


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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryIndian Institute of Technology BombayMumbaiIndia
  2. 2.Department of ChemistryPurdue UniversityWest LafayetteUSA
  3. 3.Department of ChemistryHoward UniversityWashingtonUSA

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