An observation of a folded β-ala conformation in a model peptide: BOc - L-pip - β-ala - NHCH3, X-ray diffraction study

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9553-9556

  Thakur, Ashwani K ^a   Kishore, Raghuvansh ^a  

^a INSTITUTE OF MICROBIAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BETA ALANINE; PEPTIDE;

ARTICLE; CRYSTAL STRUCTURE; PROTEIN CONFORMATION; PROTEIN FOLDING; X RAY DIFFRACTION;

EID: 0032542207     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02122-4     Document Type: Article

References (21)

1. 1. a) Aubry, A.; Marraud, M. Biopolymers, 1989, 28, 109;
2. b) Toniolo, C. Int. J. Peptide Protein Res. 1990, 35, 297;
3. c) Toniolo, C. Janssen Chim. Acta, 1993, 11, 10;
4. d) Tetrahedron, 1993, 49, 3433 (Ed. Kahn, M.);
5. e) Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc., 1994, 116, 1054.
6. 2. a) Pavone, V.; Di Blasio, B.; Lombardi, A.; Isernia, C.; Pedone, C.; Benedetti, E.; Valle, G.; Crisma, M.; Toniolo, C.; Kishore, R. J. Chem. Soc. Perkin. Trans. II, 1992, 1233;
7. (b) Bardi, R.; Piazzesi, A. M.; Crisma, M.; Toniolo, C.; Kishore, R. Zeit. Krystallogr., 1993, 207, 290;
8. c) Kishore, R. Tetrahedron Lett., 1996, 37, 5747.
9. 3. Karle, I. L.; Handa, B. K.; Hassal, C. H. Acta Crystallogr., Sect. B, 1975, 31, 555.
10. 4. a) Di Blasio, B.; Lombardi, A.; Yang, X.; Pedone, C.; Pavone, V. Biopolymers, 1991, 31, 1181;
11. b) Cerrini, S.; Gavuzzo, E.; Lucente, G.; Pinnen, F.; Zanotti, G. Int. J. Peptide Protein Res., 1989, 33, 6;
12. c) Lombardi, A.; Saviano, M.; Nastri, F.; Fattorusso, R.; Maglio, O.; Mazzeo, M.; Pedone, C.; lsernia, C.; Pavone, V. Biopolymers, 1996, 38, 683;
13. d) Benedetti, E. Biopolymers (Peptide Science), 1996, 40, 3 and references therein.
14. -3, T = 293 K, Final R = 0.0708, Final Rw = 0.2185. Details of synthesis, purification and characterization and crystal structure determination by application of direct method programmes (SHELX - 97) shall be reported elsewhere.
15. 6. a) Toniolo, C.; Bardi, R.; Piazzesi, A. M.; Crisma, M.; Balaram, P.; Sukumar, M.; Paul, P. K. C. (Eds. Jung, G. and Bayer, E.). in "Peptides 1988", 477. de Gruyter, W. Berlin. 1989;
16. b) 1b.
17. c)Bardi, R.; Piazzesi, A. M.; Crisma, M.; Toniolo, C. Acta Crystallogr., 1992, C48, 1645.
18. 7. Benedetti, E.; Pedone, C.; Toniolo, C.; Pottle, S. M.; Scheraga, H. A. Int. J. Peptide Protein Res., 1980, 6, 156.
19. 8. a) Zimmerman, S. S.; Scheraga, H. A. Biopolymers, 1977, 16, 811;
20. b) Prasad, B. V. V.; Balaram, P. CRC Crit. Rev. Biochem., 1984, 16, 307;
21. c) Toniolo, C. CRC. Crit. Rev. Biochem., 1980, 9, 1; It is noteworthy that while the Aib residue restricts the backbone torsion angles in the helical regions (φ ≈ ±60±20°, ψ ≈ ±30±20°) the five membered pyrrolidine ring of the Pro resiue restricts the φ values in the range -65±15°, of the conformational space.