Nα -Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis

Organic & Biomolecular Chemistry
Eva SchütznerováViktor Krchnák

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.

References

Jun 9, 1977·Nature·J A LordH W Kosterlitz
Jun 18, 1969·Journal of the American Chemical Society·L R Fedor, J McLaughlin
Jul 11, 2003·Bioorganic & Medicinal Chemistry Letters·Zhanxiang LiuXian Huang
Sep 2, 2009·Angewandte Chemie·Tanja KnothHerbert Waldmann
Feb 7, 2012·Mini Reviews in Medicinal Chemistry·R SaladinoM Crucianelli
Jul 19, 2012·Organic Letters·Wen-Ju BaiThomas R R Pettus
Jul 29, 2015·Chemistry : a European Journal·Pilar Ventosa-AndrésViktor Krchňák

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Citations

Apr 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Eva SchütznerováViktor Krchňák

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Methods Mentioned

BETA
acylation
NMR

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