Side-chain chiral centers of amino acid and helical-screw handedness of its peptides

Journal of the American Chemical Society

Volumn 127, Issue 33, 2005, Pages 11570-11571

  Tanaka, Masakazu ^a   Anan, Kosuke ^a   Demizu, Yosuke ^a   Kurihara, Masaaki ^b   Doi, Mitsunobu ^c   Suemune, Hiroshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^c OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID ANALYSIS; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHIRALITY; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; HARDNESS; HYDROGEN BOND; HYDROGENATION; HYDROLYSIS; INFRARED SPECTROSCOPY; OZONOLYSIS; PROTEIN CONFORMATION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 23944525335     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053842c     Document Type: Article

References (20)

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5. (a) Tanaka, M.; Demizu, Y.; Doi, M.; Kurihara, M.; Suemune, H. Angew. Chem., Int. Ed. 2004, 43, 5360-5363.
6. (b) Royo, S.; Borggraeve, W. M. D.; Peggion, C.; Formaggio, F.; Crisma, M.; Jimenez, A. I.; Cativiela, C.; Toniolo, C. J. Am. Chem. Soc. 2005, 127, 2036-2037.
7. 5,6c: (1R,6R)-8-aminobicyclo[4.3.0]nonane-8- carboxylic acid; HBTU:O-benzotriazol-1-yl-N,N,N′N′- tetramethyluronium hexafluorophosphate; TEMPO: 2,2,6,6-tetramethyl-1- piperidinoxyl, free radical; TFE: 2,2,2-trifluoroethanol.
8. For peptides composed of dAA with axial chirality, see: (a) Mazaleyrat, J. P.; Wright, K.; Gaucher, A.; Wakselman, M.; Oancea, S.; Formaggio, F.; Toniolo, C.; Setnicka, V.; Kapitan, J.; Keiderling, T. A. Tetrahedron: Asymmetry 2003, 14, 1879-1893.
9. (b) Mazaleyrat, J.-P.; Wright, K.; Gaucher, A.; Toulemonde, N.; Wakselman, M.; Oancea, S.; Peggion, C.; Formaggio, F.; Sentnicka, V.; Keiderling, T. A.; Toniolo, C. J. Am. Chem. Soc. 2004, 126, 12874-12879.
10. See chiral peptoids: Wu, C. W.; Kirshenbaum, K.; Sanborn, T. J.; Patch, J. A.; Huang, K.; Dill, K. A.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2003, 125, 13525-13530.
11. Bernardi, A.; Arosio, D.; Dellavecchia, D.; Micheli, F. Tetrahedron: Asymmetry 1999, 10, 3403-3407.
12. (a) Cativiela, C.; de Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732.
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14. See Supporting Information.
15. Santini, A.; Barone, V.; Bavoso, A.; Benedetti, E.; Di Blasio, B.; Fraternali, F.; Lelj, F.; Pavone, V.; Pedone, C.; Crisma, M.; Bonora, G. M.; Toniolo, C. Int. J. Biol. Macromol. 1988, 10, 292-299 and 300-304.
16. Sheldrick, G. M. SHELXS-97. Program for the solution of crystal structures from diffraction data. University of Göttingen: Göttingen, Germany, 1997.
17. 2(1 > 2σ) = 0.1373, GOF = 0.885.
18. The signs of φ, ψ torsion angles at the C-terminus are opposite to those of the preceding residues. Thus, the mean values refer to those of the amino acid residues 1-5, respectively.
19. 10-helices of peptides having the main-chain asymmetric centers have already been reported. See: (a) Valle, G.; Crisma, M.; Toniolo, C.; Besswenger, R.; Rieker, A.; Jung, G. J. Am. Chem. Soc. 1989, 111, 6828-6833.
20. (b) Jaun, B.; Tanaka, M.; Seiler, P.; Kühnle, F. N. M.; Braun, C.; Seebach, D. Liebigs Ann. Recueil 1997, 1697-1710.