Configurationally driven folding of model tetrapeptides containing L- or D-morpholine-3-carboxylic acids as beta-turn nucleators

Chirality
Andrea TrabocchiAntonio Guarna

Abstract

The conformational analysis by NMR, IR, and molecular modeling of tetrapeptides containing morpholine-3-carboxylic acid (Mor) as a proline surrogate is presented. The relationship between the chirality of the cyclic amino acid at position i+1 and the turn propensity is maintained with respect to the reference proline-containing peptides, although marked differences in the type of folded structures were observed. The conformational profile of morpholine-containing turn peptides as a function of the chirality of the cyclic amino acid indicated that the heterochiral tetrapeptide containing the D-isomer of the cyclic amino acid is more prone to nucleate compact folded structures, although with no resemblance to the beta-turn structures of D-proline-containing peptides. Also, the solvation system proved to influence the organization of folded structures, as in the more interactive CD(3)CN the model peptides showed more compact conformations. The L-Mor-containing peptide displayed two rotamers at the Val-Mor amide bond. The trans isomer did not experience any turn structures, nor any intramolecular hydrogen-bonds, whereas the cis isomer showed a strong preference for a type VI beta-turn structure, thus providing a different conformat...Continue Reading

References

Jan 1, 1992·Annual Review of Biochemistry·J Rizo, L M Gierasch
Jan 1, 1985·Advances in Protein Chemistry·G D RoseJ A Smith
Nov 5, 1998·Bioorganic & Medicinal Chemistry·S J StachelD L Van Vranken
May 24, 2000·Organic Letters·Y FengK Burgess
Sep 18, 2001·The Journal of Organic Chemistry·E AlonsoJ González
May 2, 1997·The Journal of Organic Chemistry·Kyonghee Kim, Juris P. Germanas
Oct 25, 2001·The Journal of Organic Chemistry·Michael J. Soth, James S. Nowick
Mar 14, 2002·Journal of the American Chemical Society·Liliane Halab, William D Lubell
Dec 8, 2004·Bioorganic & Medicinal Chemistry Letters·Jun ChibaAngela Wong
Aug 9, 2005·Bioorganic & Medicinal Chemistry Letters·J I LevinJ S Skotnicki
May 1, 2007·The Journal of Organic Chemistry·Filippo SladojevichAntonio Guarna

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Citations

Feb 6, 2010·Organic & Biomolecular Chemistry·Filippo SladojevichAndrea Trabocchi
Sep 30, 2009·The Journal of Organic Chemistry·Giordano LesmaAlessandra Silvani
Oct 1, 2009·The Journal of Organic Chemistry·Karine GuitotUmberto Piarulli
Jan 13, 2011·The Journal of Organic Chemistry·Alessandro SacchettiTullio Pilati

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