Entrapping unusual folding characteristics of the β-Ala residues in a model peptide: Boc-β-Ala-Aib- β-Ala-NHCH3

Journal of Peptide Research

Volumn 56, Issue 1, 2000, Pages 55-58

  Thakur, A K ^a   Venugopalan, P ^b   Kishore, R ^a  

^a INSTITUTE OF MICROBIAL TECHNOLOGY   (India)

^b PANJAB UNIVERSITY   (India)

Author keywords

Ala peptides; Folded structures; Peptide design; Unusual H bond; X ray diffraction analysis

Indexed keywords

2 AMINO 2 METHYLPROPIONIC ACID; BETA ALANINE; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTEIN FOLDING;

BETA-ALANINE; HYDROGEN BONDING; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PROTEIN CONFORMATION; PROTEIN FOLDING; X-RAY DIFFRACTION;

EID: 0002270058     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2000.00737.x     Document Type: Article

References (17)

1. 1. Benedetti, E. (1996) X-ray crystallography of peptides. Biopolymers (Peptide Sci.) 40, 3-44.
2. 2. DeGrado, W.F., Scheider, J.P. & Hanuro, Y. (1999) The twist and turns of β-peptides. J. Peptide Res. 54, 206-217.
3. 3. Benedetti, E., Bavoso, A., Di Blasio, B., Grimaldi, P., Pavone, V., Pedone, C., Toniolo, C. & Bonora, G.M. (1985) Linear oligopeptides - effect of lengthening of the mainchain by one tetrahedral carbon atom in the -Aib-Ala-sequence: a solid state conformational analysis of segments of polypeptide antibiotics. Int. J. Biol. Macromol. 7, 81-88.
4. 4. Pavone, V., Di Blasio, B., Lombardi, A., Isernia, C., Pedone, C., Benedetti, E., Valle, G., Crisma, M., Toniolo, C. & Kishore, R. (1992) β-Alanine and β-bends. X-ray diffraction structures of three linear oligopeptides. J. Chem. Soc. Perkin Trans. 2, 1233-1237.
5. 2-NH propyl. Biopolymers 32, 643-648.
6. 6. Crisma M., Formaggio, F., Toniolo, C., Yoshikawa, T. & Wakamiya, T.J. (1999) Flat peptides. J. Am. Chem. Soc. 121, 3272-3278.
7. 7. Kishore, R. (1996) Identification of novel stereogeometrical features in β-Ala residues. Tetrahedron Lett. 37, 5747-5750.
8. 3, X-ray diffraction study. Tetrahedron Lett. 39, 9553-9556.
9. 9. Thakur, A.K. & Kishore, R. (1999) An all-anti conformation of the β-Ala moiety in the crystalline state. Tetrahedron Lett. 40, 5091-5094.
10. 3. Tetrahedron 55, 13791-13804.
11. 11. Thakur, A.K. & Kishore, R. (2000) Stabilization of a novel β-turn like motif by non-conventional intramolecular hydrogen bonding interactions in a model peptide containing β-alanine. Biopolymers 53, 447-454.
12. 12. Desiraju, G.R. (1995) Supramolecular synthons in crystal engineering - a new organic synthesis. Angew. Chem. Int. Engl. 34, 2311-2327.
13. 13. Desiraju, G.R. (1996) The C-H⋯O hydrogen bond: structural implications and supramolecular design. Acc. Chem. Res. 19, 441-449.
14. 14. Gellman, S.H., Powell, D.R. & Desper, J.M. (1992) An unusual hydrogen bonding pattern in a crystallographically observed β-turn. Tetrahedron Lett. 33, 1963-1964.
15. 15. Wu, Y.-D. & Wang, D.-P. (1998) Theoretical studies of -peptide models. J. Am. Chem. Soc. 120, 13485-13493.
16. 16. Wrighton, N.C., Balasubramanian, P., Barbone, F.P., Kashyap, A.K., Farrell, F.X., Jolliffe, L.K., Barrett, R.W. & Dower, W.J. (1997) Increased potency of an crythropoietin peptide mimetic through covalent dimerization. Nature Biotech. 15, 1261-1165.
17. 17. Sheldrick, G.M. (1997) SHELXS-97. Program for Crystal Structure Solution and Refinement. Göttingen University, Germany.