Crystal structure of cyclo(Adm-Cyst)3: Example of a topologically defined double-helical cystine cyclic peptide

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10916-10917

  Karle, Isabella L ^a   Ranganathan, Darshan ^b   Haridas, V ^b  

^a NAVAL RESEARCH LABORATORY   (United States)

^b REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; CYCLOPEPTIDE; MACROCYCLIC COMPOUND;

ARTICLE; CHIRALITY; DRUG STRUCTURE;

EID: 0029840852     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961741w     Document Type: Article

References (23)

1. Sumners, D. W. The Role of Knot Theory in DNA Research. In Geometry and Topology; McCrory, C., Schifrin, T., Eds.; Marcel Dekker: New York, 1987; pp 297-318. Dietrich-Buchecker, C. O.; Sauvage, J.-P. Interlocked and Knotted Rings in Biology and Chemistry. In Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer-Verlag: Berlin, 1991; Vol. 2, pp 195-248. Bates, A. D.; Maxwell, A. DNA Topology; Oxford University Press: New York, 1993.
2. Sumners, D. W. The Role of Knot Theory in DNA Research. In Geometry and Topology; McCrory, C., Schifrin, T., Eds.; Marcel Dekker: New York, 1987; pp 297-318. Dietrich-Buchecker, C. O.; Sauvage, J.-P. Interlocked and Knotted Rings in Biology and Chemistry. In Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer-Verlag: Berlin, 1991; Vol. 2, pp 195-248. Bates, A. D.; Maxwell, A. DNA Topology; Oxford University Press: New York, 1993.
3. Sumners, D. W. The Role of Knot Theory in DNA Research. In Geometry and Topology; McCrory, C., Schifrin, T., Eds.; Marcel Dekker: New York, 1987; pp 297-318. Dietrich-Buchecker, C. O.; Sauvage, J.-P. Interlocked and Knotted Rings in Biology and Chemistry. In Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer-Verlag: Berlin, 1991; Vol. 2, pp 195-248. Bates, A. D.; Maxwell, A. DNA Topology; Oxford University Press: New York, 1993.
4. Mansfield, M. L. Nat. Struct. Biol. 1994, 1, 213. Liang, C.; Mislow, K. J. Am. Chem. Soc. 1994, 116, 3588.
5. Mansfield, M. L. Nat. Struct. Biol. 1994, 1, 213. Liang, C.; Mislow, K. J. Am. Chem. Soc. 1994, 116, 3588.
6. The only topological link known to date that is composed entirely of amino acid residues is the catenated structure of β-subunit of human chorionic gonadotropin (see ref 6 in Liang, C.; Mislow, K. J. Am. Chem. Soc. 1994, 116, 11189).
7. Metal atoms and disulfide bonds are found to be integral constituents of knots and links in proteins exhibiting extraordinary topological features (Liang, C.; Mislow, K. J. Am. Chem. Soc. 1989, 111, 6132).
8. Ranganathan, D.; Haridas, V.; Madhusudanan, K. P.; Roy, R.; Nagaraj, R.; John, G. B.; Sukhaswami, M. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1105.
9. A rotaxane-like structural motif of three cystine residues in various growth factors and related proteins has been widely referred to as a knot (McDonald, N. Q.; Hendrickson, W. A. Cell 1993, 73, 421. Schlunegger, M. P.; Grutter, M. G. J. Mol. Biol. 1993, 231, 445. Murray-Rust, J.; McDonald, N. W.; Blundell, T. L.; Hosang, M.; Oefner, C.; Winkler, F.; Bradshaw, R. A. Structure 1993, 1, 153).
10. A rotaxane-like structural motif of three cystine residues in various growth factors and related proteins has been widely referred to as a knot (McDonald, N. Q.; Hendrickson, W. A. Cell 1993, 73, 421. Schlunegger, M. P.; Grutter, M. G. J. Mol. Biol. 1993, 231, 445. Murray-Rust, J.; McDonald, N. W.; Blundell, T. L.; Hosang, M.; Oefner, C.; Winkler, F.; Bradshaw, R. A. Structure 1993, 1, 153).
11. A rotaxane-like structural motif of three cystine residues in various growth factors and related proteins has been widely referred to as a knot (McDonald, N. Q.; Hendrickson, W. A. Cell 1993, 73, 421. Schlunegger, M. P.; Grutter, M. G. J. Mol. Biol. 1993, 231, 445. Murray-Rust, J.; McDonald, N. W.; Blundell, T. L.; Hosang, M.; Oefner, C.; Winkler, F.; Bradshaw, R. A. Structure 1993, 1, 153).
12. + - Adm-Cyst + H].
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14. Karle, I. L.; Kishore, S.; Raghothama, S.; Balaram, P. J. Am. Chem. Soc. 1988, 110, 1958.
15. Karle, I. L.; Flippen-Anderson, J. L. J. Am. Chem. Soc. 1988, 110, 3253.
16. 3, Z = 4, Cu radiation, λ = 1.5418 Å. Crystals were obtained from chloroform and ethyl acetate. The molecule lies on a 2-fold axis. The structure was solved by direct phase determination and refined by full-matrix anisotropic least squares. Distance restraints were applied to the disordered ethyl acetate molecule that lies on a 2-fold axis, to one methyl ester group with high mobility and one C-S-S-C group highly disordered around a crystallographic 2-fold axis. R = 9.1 for 433 parameters and 2130 independent data (>3σ(F)).
17. Although a "figure-eight" motif has been observed in the solid state structures of some molecules, for example, in turcasarin, an expanded porphyrin macrocycle containing 10 pyrrole rings (Sessler, J. L.; Weghorn, S. J.; Lynch, V.; Johnson, M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1509), and in a copper(I) complex of macrocyclic bis(dithiadiimine) ligands (Comba, P.; Fath, A.; Hambley, T. W.; Richens, D. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1883), to our knowledge the present report is the first example of a cyclic cystine peptide exhibiting a chiral "figure-eight" motif.
18. Although a "figure-eight" motif has been observed in the solid state structures of some molecules, for example, in turcasarin, an expanded porphyrin macrocycle containing 10 pyrrole rings (Sessler, J. L.; Weghorn, S. J.; Lynch, V.; Johnson, M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1509), and in a copper(I) complex of macrocyclic bis(dithiadiimine) ligands (Comba, P.; Fath, A.; Hambley, T. W.; Richens, D. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1883), to our knowledge the present report is the first example of a cyclic cystine peptide exhibiting a chiral "figure-eight" motif.
19. 14 which augurs well with the figure-eight conformation in the solid state.
20. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1.
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22. Karle. I. L.; Ranganathan, D.; Haridas, V. Unpublished results.
23. Toniolo, C.; Crisma, M.; Bonora, G. M.; Benedetti, E.; di Blasio, B.; Pavone, V.; Redone, C.; Santini, A. Biopolymers 1991, 31, 129.