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One-Pot Synthesis of New Class of Dithiocarbonate-Tethered Peptidomimetics

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Abstract

A simple and an efficient one-pot protocol for the synthesis of a new class of dithiocarbonate-tethered peptidomimetics and neo-glycosylated amino acids have been developed. This synthetic process involves in situ generation of a dithiocarbonate salt from the Nα-protected aminol substrate by reacting with CS2 followed by addition of bromo amino acid/sugar bromide to form the desired products. Amino acids with simple as well as bifunctional side chains were employed to obtain dithiocarbonate-tethered peptidomimetics in good yields. Further, the protocol was extended for the synthesis of N,N′-orthogonally protected dithiocarbonate-tethered peptidomimetics.

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Acknowledgments

We sincerely thankful to Council of Scientific and Industrial Research (CSIR) Grant No. 02(0149)/13/EMR-II Government of India, New Delhi for financial support.

Conflict of interest

Muniyappa Krishnamurthy, Basavaprabhu, Vommina V. Sureshbabu declare that they have no conflict of interest.

Human and Animal Rights and Informed Consent

Authors declare that there is no informed consent in the article. This article does not contain any studies with human or animal subjects performed by the any of the authors.

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Authors and Affiliations

  1. #109, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore, 560 001, India

    Muniyappa Krishnamurthy,  Basavaprabhu & Vommina V. Sureshbabu

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  1. Muniyappa Krishnamurthy
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  2. Basavaprabhu
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  3. Vommina V. Sureshbabu
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Correspondence to Vommina V. Sureshbabu.

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Krishnamurthy, M., Basavaprabhu & Sureshbabu, V.V. One-Pot Synthesis of New Class of Dithiocarbonate-Tethered Peptidomimetics. Int J Pept Res Ther 21, 195–203 (2015). https://doi.org/10.1007/s10989-014-9448-2

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  • DOI: https://doi.org/10.1007/s10989-014-9448-2

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