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Nα-Amino Acids Containing Privileged Structure: Design, Synthesis and Use in Solid-Phase Peptide Synthesis

Abstract

Fmoc-Protected Nα-amino acids containing a heterocyclic privileged structure, O-(1-methyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)-L-serine and O-((S)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)-L-serine, were synthesized on solid phase from simple commercially available building blocks under mild conditions. The amino acid side-chain is composed of tetramic acid, a privileged structure originating from a natural product. The key transformation was the formation of cyclic enol ethers via nonclassical Witting olefinations of the esters. Solid-phase synthesis represents a method of choice, particularly for the synthesis of peptides. This route is compatible with traditional Merrifield solid-phase peptide synthesis (SPPS), as documented in the preparation of pentapeptide Leu-enkephalin amide H-Tyr-Gly-Gly-Phe-Leu-NH2 with the Phe or Tyr replaced by novel amino acid.

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Publication details

The article was received on 23 Jun 2018, accepted on 09 Jul 2018 and first published on 12 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01485J
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Nα-Amino Acids Containing Privileged Structure: Design, Synthesis and Use in Solid-Phase Peptide Synthesis

    E. Schutznerova, A. Pribylka and V. Krchňák, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB01485J

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