An all-anti conformation of the β-Ala moiety in the crystalline state

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5091-5094

  Thakur, A K ^a   Kishore, R ^a  

^a INSTITUTE OF MICROBIAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BETA ALANINE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS; QUANTUM MECHANICS;

EID: 0033516550     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00989-2     Document Type: Article

References (27)

1. a) Griffith, O. W. Annu, Rev. Biochem. 1986, 55, 855;
2. b) Edmundson, A. B.; Harris, D. L.; Fan, Z. C.; Guddat, L. W.; Schley, B. T.; Hanson, B. L.; Tribbick, G.; Geysen, H. M. Proteins: Struct., Funct. and Genet. 1993, 16, 246;
3. c) Saviano, G.; Temussi, P. A.; Motta, A.; Maggi, C. A.; Rovero, P. Biochemistry 1991, 30, 10176;
4. d) Wrighton, N. C.; Balasubramanian, P.; Barbone, F. P.; Kashyap, A. K.; Farrell, F. X.; Jlliffe, L. K.; Barrett, R. W.; Dower, W. J. Nature Biotech. 1997, 15, 1261;
5. e) Benedetti, E. Biopolymers (Peptide Science) 1996, 40, 3;
6. f) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173;
7. g) Appella, D. H.; Christianson, L. A.; Klein, D. A.; Powell, D. R.; Huang, X.; Barchi, J. J. Jr.; Gellman, S. H. Nature 1997, 387, 381.
8. a) 1a; b) Rodriguez, M.; Fulcrand, P.; Laur, J.; Aumelas, A.; Bali, J. P.; Martinez, J. J. Med. Chem. 1989, 32, 522;
9. c) Rane, D. F.; Girijavallabhan, V. M.; Ganguly, A. K.; Pike, R. E.; Saksena, A. K.; Mackphail. A. T. Tetrahedron Lett. 1993, 34, 3201;
10. d) Seebach, D.; Overhand, M.; Kuhnle, N. M.; Martinoni, B. Helv. Chim. Acta 1996, 79, 913.
11. a) Benedetti, E.; Bavoso, A.; Di Blasio, B.; Grimaldi, P.; Pavone, V.; Pedone, C.; Toniolo, C.; Bonora, G. M. Int. J. Biol. Macromol. 1985, 7, 81;
12. b) Aubry, A.; Marraud, M. Biopolymers 1989. 28, 109;
13. c) 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. 2 1992, 1233;
14. d) Bardi, R.; Piazzesi, A. M.; Crisma, M.; Toniolo, C.; Kishore, R. Zeit. Krystallogr. 1993, 207, 290;
15. e) Kishore, R. Tetrahedron Lett. 1996, 37, 5747;
16. f) 1e; g) Thakur, A. K.; Kishore, R. Tetrahedron Lett. 1998, 39, 9553.
17. Wu, Y.-D.; Wang, D.-P. J. Am. Chem. Soc. 1998, 120, 13485.
18. a) Navarro, E.; Alemán, C.; Puiggali, J. J. Am. Chem. Soc. 1995, 117, 7307;
19. b) Navarro, E.; Aleman, C.; Puiggali, J. Macromol. 1998, 31, 408 and references therein.
20. -3, T = 293 K, Final R = 0.0757, Final Rw = 0.2465. Details of crystal structure determination by application of direct method programmes SHELX-97, will be reported elsewhere.
21. Valle, G.; Bonora, G. M.; Toniolo,C. Gazz. Chim. Ital. 1984, 114, 341.
22. a) Pavone, V.; Benedetti, E.; Di Blasio, B; Lombardi, A.; Pedone, C.; Lorenzi, G. P. Biopolymers 1993, 28, 215;
23. b) Sun, X. C.; Lorenzi, G. P. Helv. Chim. Acta 1994, 77, 1520;
24. c) Bandekar, J. Biochim. Biophys. Acta 1992, 1120, 123.
25. -1. In conjunction with NMR data the results indicated that intramolecular H-bonded ring structures are disfavoured.
26. a) Smith, D. A.; Vijaykumar, S. Tetrahedron Lett. 1991, 32, 3616;
27. b) Gellman, S. H.; Dado, G. P. Tetrahedron Lett. 1991, 32, 7377 and references therein.