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Issue 29, 2018
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N α-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis

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Abstract

Fmoc-protected Nα-amino acid containing heterocyclic privileged structures, 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 the solid phase from simple commercially available building blocks under mild conditions. The amino acid side-chain is composed of tetramic acid, a natural product derived privileged structure. The key transformation was the formation of cyclic enol ethers via nonclassical Wittig 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 on the preparation of the pentapeptide Leu-enkephalin amide H-Tyr-Gly-Gly-Phe-Leu-NH2 with Phe or Tyr replaced by a novel amino acid.

Graphical abstract: N α-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis

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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., 2018,16, 5359-5362
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    N α-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis

    E. Schütznerová, A. Přibylka and V. Krchňák, Org. Biomol. Chem., 2018, 16, 5359
    DOI: 10.1039/C8OB01485J

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