Abstract
Conveniently substituted 2-alkyl-2-carboxyazetidine amino acids have been incorporated into NGF and NT3 tetrapeptide sequences to investigate their utility as reverse turn inducers (γ- vs. β-turns). Despite the presence of an Asp residue at i position, highly preferred in β-turns, molecular modeling and NMR studies indicated that the azetidine-containing peptides mainly stabilized γ-turn conformations.
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Notes
For a new nomenclature of azetidine containing amino acids (see Bonache 2006). Azx indicates any azetidine, Aze, Azk and Azo refer to Glu, Lys and Nle-derived azetidines, respectively.
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Acknowledgments
This work has been supported by CICYT (SAF 2006-01205 and SAF2009-09323). J. L. B. was a predoctoral FPI fellow. The “Centro Técnico de Informática (CTI-CSIC)” granted computer time.
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Baeza, J.L., Bonache, M.Á., García-López, M.T. et al. 2-Alkyl-2-carboxyazetidines as γ-turn inducers: incorporation into neurotrophin fragments. Amino Acids 39, 1299–1307 (2010). https://doi.org/10.1007/s00726-010-0569-4
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DOI: https://doi.org/10.1007/s00726-010-0569-4