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Synthesis of Peptides Employing Protected-Amino Acid Halides Mediated by Commercial Anion Exchange Resin

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Abstract

Coupling of protected-amino acid halides (chloride, fluoride) mediated by commercial anion exchange resin for the solution phase synthesis of peptides is described. The reaction was carried out in an organic medium, circumventing the use of an organic base or an inorganic base. The coupling is fast, clean and racemization free. The anion exchange resin functions as a solid-phase basic scavenger, soaking up the HCl produced and allowing the amine to react. The method is extended for the coupling of sterically hindered α,α,-dialkylamino acids.

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Scheme 1
Fig. 1
Fig. 2

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Abbreviations

IER:

Ionexchange resin

Phg:

Phenylglycine

DCM:

Dichlromethane

DIEA:

Diisopropylethylamine

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Authors and Affiliations

  1. Mylan Laboratories Ltd., Chemical Research Division, Anrich Industrial Estate, Bollaram, Hyderabad, 502325, India

    K. M. Bhaskara Redddy & Kuppanna Ananda

  2. Department of Chemistry, College of Engineering, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad, 500085, India

    Y. Bharathi Kumari

Authors
  1. K. M. Bhaskara Redddy
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  2. Y. Bharathi Kumari
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  3. Kuppanna Ananda
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Correspondence to Kuppanna Ananda.

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Bhaskara Redddy, K.M., Kumari, Y.B. & Ananda, K. Synthesis of Peptides Employing Protected-Amino Acid Halides Mediated by Commercial Anion Exchange Resin. Int J Pept Res Ther 19, 225–229 (2013). https://doi.org/10.1007/s10989-012-9337-5

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  • DOI: https://doi.org/10.1007/s10989-012-9337-5

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