Trishomocubane amino acid as a beta-turn scaffold

Chemical Biology & Drug Design
Fernando AlbericioSamran Prabpai

Abstract

The synthesis and X-ray structure of two diasteriomeric heptapeptides [Ac-Ala-Ala-Ala-(R/S)-Cage-Ala-Ala-Ala-NH2] with a trishomocubane amino acid as a beta-turn scaffold are reported. The amino acid was synthesized as a racemate and two diastereomeric peptides were obtained. The two peptides were separated by preparative high-pressure liquid chromatography and crystals suitable for X-ray analysis were grown for both diasteriomeric peptides. In general, both the peptides satisfy the criteria for beta-turn conformations. Five of the six Ala residues of both cage peptide crystals satisfy the criteria for 3(10)-helix characteristics and the cage amino acid residue satisfied the alpha-helix classification. These experimental results confirm previous theoretical studies in our laboratory which predicted that the cage moiety would be a strong/active beta-turn inducer.

References

Sep 15, 1977·Journal of Molecular Biology·P Y Chou, G D Fasman
Sep 1, 1991·Trends in Biochemical Sciences·C Toniolo, E Benedetti
Jan 1, 1985·Advances in Protein Chemistry·G D RoseJ A Smith
Oct 21, 1986·Biochemistry·J R RoesserS M Hecht
Jul 11, 1985·Nature·B L Sibanda, J M Thornton
Apr 20, 1973·Biochimica Et Biophysica Acta·P N LewisH A Scheraga
Apr 26, 2000·Chemistry & Biology·A G Cochran
Nov 17, 2001·Chemical Reviews·R P ChengW F DeGrado
Dec 26, 2001·Chemical Reviews·M W Peczuh, A D Hamilton
Apr 18, 2002·Bioorganic & Medicinal Chemistry Letters·Edgar Jacoby
Jul 15, 2003·The Journal of Biological Chemistry·Jürgen ZimmermannLinda J Ball
May 27, 2004·Journal of Peptide Science : an Official Publication of the European Peptide Society·Krishna BisettyJuan J Perez
Aug 5, 2004·Journal of the American Chemical Society·Joshua A KritzerAlanna Schepartz
Dec 8, 2004·Bioorganic & Medicinal Chemistry·Joshua A KritzerAlanna Schepartz
Jan 7, 2005·Journal of Medicinal Chemistry·Buddhadeb MallikJohn D Lambris
Mar 15, 2005·Angewandte Chemie·Hang YinAndrew D Hamilton
Apr 28, 2005·Current Protein & Peptide Science·Laurel O Sillerud, Richard S Larson
Jun 11, 2005·Bioorganic & Medicinal Chemistry Letters·Eric Enholm, Ashwin Bharadwaj
Jun 14, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Krishna BisettyJuan J Perez
Jul 16, 2005·The Journal of Organic Chemistry·Ravindranadh V Somu, Rodney L Johnson
Dec 13, 2005·Journal of Medicinal Chemistry·Olga Labudda-DawidowskaBernard Lammek
Dec 14, 2005·Biopolymers·Krishna BisettyHendrik G Kruger
Feb 8, 2007·Journal of the American Chemical Society·Federico BernalGregory L Verdine
Mar 31, 2007·Science·Hang YinWilliam F DeGrado
Apr 10, 2007·Bioorganic & Medicinal Chemistry Letters·Akiyoshi HirataTakashi Morii
Apr 18, 2007·Nature Chemical Biology·Catherine M GoodmanWilliam F DeGrado

❮ Previous
Next ❯

Citations

Feb 4, 2010·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Nathan T RossAndrew D Hamilton
Apr 19, 2015·Journal of Biomedical Science·Bahareh HonarparvarHendrik G Kruger
Sep 30, 2015·Chemistry : a European Journal·Misal Giuseppe MemeoPaolo Quadrelli
Nov 15, 2011·Journal of Peptide Science : an Official Publication of the European Peptide Society·Maya MakatiniHendrik G Kruger
Feb 18, 2014·Archiv der Pharmazie·Nikola BasarićJan Balzarini
May 18, 2010·Magnetic Resonance in Chemistry : MRC·Mohamed S AltaibHendrik G Kruger
May 23, 2014·Organic & Biomolecular Chemistry·Majid D FarahaniHendrik G Kruger
Jun 11, 2011·Organic Letters·Andrea PinskerPeter Gmeiner
May 18, 2018·The Journal of Organic Chemistry·Sambasivarao Kotha, Subba Rao Cheekatla

❮ Previous
Next ❯

Related Concepts

Related Feeds

Autoimmune Diseases

Autoimmune diseases occur as a result of an attack by the immune system on the body’s own tissues resulting in damage and dysfunction. There are different types of autoimmune diseases, in which there is a complex and unknown interaction between genetics and the environment. Discover the latest research on autoimmune diseases here.

Related Papers

Magnetic Resonance in Chemistry : MRC
Mohamed S AltaibHendrik G Kruger
Journal of Peptide Science : an Official Publication of the European Peptide Society
Krishna BisettyJuan J Perez
Journal of Peptide Science : an Official Publication of the European Peptide Society
E EscuderoJ A Subirana
© 2021 Meta ULC. All rights reserved