Disulfide chromophore and its optical activity

Chirality

Volumn 22, Issue 1 E, 2010, Pages

  Maloň, Petr ^a   Bednárová, Lucie ^a   Straka, Michal ^a   Krejňí, Lucie ^a   Kumprecht, Lukáš ^a   Kraus, Tomáš ^a   Kubáňová, Markéta ^b   Baumruk, Vladimír ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

D cyclodextrin; circular dichroism; disulfide bridge; Raman optical activity; spectroscopy; vibrational optical activity

Indexed keywords

ALPHA CYCLODEXTRIN DERIVATIVE; AMIDE; AMINO ACID DERIVATIVE; DISULFIDE;

ADSORPTION; CHROMATOPHORE; CIRCULAR DICHROISM; CONFERENCE PAPER; CONTROLLED STUDY; DISULFIDE BOND; ELECTRONICS; OPTICS; PRIORITY JOURNAL; RAMAN SPECTROMETRY;

ALPHA-CYCLODEXTRINS; CIRCULAR DICHROISM; DISULFIDES; MOLECULAR STRUCTURE; SPECTRUM ANALYSIS, RAMAN; VIBRATION;

EID: 78349258894     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20851     Document Type: Conference Paper

References (41)

1. Miyazawa T,. Infrared spectra and helical conformations. In:, Fasman GD, editor. Poly-α-amino acids: proteins models for conformational analysis. New York: Dekker; 1967. p 69 103.
2. Fasman GD,. Prediction of protein structure and the principles of protein conformation. New York: Plenum; 1989.
3. Richardson JS, Richardson DC,. Principles and patterns of protein conformation. In:, Fasman GD, editor. Prediction of protein structure and the principles of protein conformation. New York: Plenum; 1989. p 1 98.
4. Keiderling TA,. Protein structural studies using vibrational circular dichroism spectroscopy In:, Havel HA, editor. Determination of protein structure in solution by spectrocopic methods. New York: VCH Publ.; 1993. p 163 188.
5. Hollosi M, Majer Z, Ronai AZ, Magyar A, Medzihradszky K, Holly S, Perczel A, Fasman GD,. CD and Fourier-transform IR spectroscopic studies of peptides. 2. Detection of beta-turns in linear peptides. Biopolymers 1994; 34: 177 185.
6. Keiderling TA,. Protein structural studies using vibrational circular dichroism spectroscopy. In:, Havel H, editor. Spectroscopic methods for determining protein structure in solution. New York: VCH Publishers; 1995. p 163 169.
7. Barron LD, Hecht L, Bell AD,. Vibrational Raman optical activity of biomolecules. In:, Fasman GD, editor. Circular dichroism and the conformational analysis of biomolecules. New York: Plenum; 1996. p 653 695.
8. Fasman GD,. The development of the prediction of protein structure. Circular dichroism and the conformational analysis of biomolecules., Fasman GD, editor. New York: Plenum; 1996, p 193 317.
9. Havel HH,. Spectroscopic methods for determining protein structure in solution. New York: VCH; 1996.
10. Woody RW,. Theory of circular dichroism of proteins. In:, Fasman GD, editor. Circular dichroism and the conformational analysis of biomolecules. New York: Plenum Press; 1996. p 25 67.
11. Debarbieux L, Beckwith J,. Electron avenue: pathways of disulfide bond formation and isomerization. Cell 1999; 99: 117 119.
12. Wedemeyer WJ, Welker E, Narayan M, Scheraga HA,. Disulfide bonds and protein folding. Biochemistry 2000; 39: 7032 7032.
13. Wedemeyer WJ, Welker E, Narayan M, Scheraga HA,. Disulfide bonds and protein folding. Biochemistry 2000; 39: 4207 4216.
14. Richardson JS,. Anatomy and taxonomy of protein structure. Adv Protein Chem 1981; 34: 174 339.
15. Harrison PM, Sternberg MJE,. The disulphide beta-cross: from cystine geometry and clustering to classification of small disulphide-rich protein folds. J Mol Biol 1996; 264: 603 623.
16. Bednarova L, Bour P, Malon P,. Vibrational and electronic optical activity of the chiral disulphide group: implications for disulphide bridge conformation. Chirality 2010; 22: 514 526.
17. Linderberg J, Michl J,. On inherent optical activity of organic disulfides. J Am Chem Soc 1970; 92: 2619 2625.
18. Ludescher U, Schwyzer R,. Chirality of cystine disulfide groupassignment of helical sense in a model compound with a dihedral angle greater than 90 degrees using Nmr and Cd. Helv Chim Acta 1971; 54: 1637 1648.
19. Donzel B, Schwyzer R, Wuthrich K, Kamber B,. Chiral cystine disulfide group without inherent optical-activity in long-wavelength region H-1-Nmr and Nmr C-13-Nmr, Uv, Cd, and Ord-studies with cyclo- L -cystine. Helv Chim Acta 1972; 55: 947 964.
20. Woody RW,. Application of Bergson model to optical properties of chiral disulfides. Tetrahedron 1973; 29: 1273 1283.
21. Fric I, Kodicek M, Jost K, Blaha K,. Amino-acids and peptides. 120. Chiroptical properties of carba-analogs of oxytocin-conformational considerations. Collect Czech Chem Commun 1974; 39: 1271 1289.
22. Fric I, Kodicek M, Prochazka Z, Jost K, Blaha K,. Amino-acids and peptides. 121. Synthesis and circular-dichroism of some analogs of deamino-1-carba-oxytocin with modifications of amino-acid residue in position 2. Collect Czech Chem Commun 1974; 39: 1290 1302.
23. Qian WL, Krimm S,. Vibrational studies of the disulfide group in proteins. 7. Normal mode analysis of the Raman-spectra of erabutoxin, gamma-ii crystallin and immunoglobulin. J Raman Spectrosc 1992; 23: 517 521.
24. Qian WL, Krimm S,. Vibrational studies of the disulfide group in proteins. 6. General correlations of Ss and Cs stretch frequencies with disulfide bridge geometry. Biopolymers 1992; 32: 1025 1033.
25. Qian WL, Krimm S,. Conformation dependence of the Sh and Cs stretch frequencies of the cysteine residue. Biopolymers 1992; 32: 1503 1518.
26. Qian WL, Krimm S,. Vibrational studies of the disulfide group in proteins. 5. Correlation of Ss stretch frequencies with the Ccss dihedral angle in known protein disulfide bridges. Biopolymers 1992; 32: 321 326.
27. Qian WL, Zhao WY, Krimm S,. Vibrational studies of the disulfide group in proteins. 4. Ss and Cs stretch frequencies of known peptide and protein disulfide bridges. J Mol Struct 1991; 250: 89 102.
28. Kapitan J, Baumruk V, Gut V, Hlavacek J, Dlouha H, Urbanova M, Wunsch E, Malon P,. Raman optical activity of the central part of hinge peptide. Collect Czech Chem Commun 2005; 70: 403 409.
29. Kapitan J, Baumruk V, Hulacova H, Malon P,. Raman optical activity of the hinge peptide. Vib Spectrosc 2006; 42: 88 92.
30. Kapitan J, Johannessen C, Barron LD, Hecht L,. In:, Chowdhry RWaBZ, editor. Exploring conformational behavior of biopolymers with simulations of Raman optical activity spectra. London: IM publications; 2008. p 573.
31. Barron LD, Gargaro AR, Wen ZQ, MacNicol DD, Butters C,. Vibrational Raman optical activity of cyclodextrins. Tetrahedron Asymmetry 1990; 1: 513 516.
32. Bell AF, Hecht L, Barron LD,. Disaccharide solution stereochemistry from vibrational Raman optical activity. J Am Chem Soc 1994; 116: 5155 5161.
33. Krejci L, Budesinsky M, Cisarova I, Kraus T,. Tubular duplex alpha-cyclodextrin triply bridged with disulfide bonds: synthesis, crystal structure and inclusion complexes. Chem Commun 2009: 3557 3559.
34. Kumprecht L, Budesinsky M, Vondrasek J, Vymetal J, Cerny J, Cisarova I, Brynda J, Herzig V, Koutnik P, Zavada J, Kraus T,. Rigid duplex alpha-cyclodextrin reversibly connected with disulfide bonds. Synthesis and inclusion complexes. J Org Chem 2009; 74: 1082 1092; (Erratum in 2009;l 74:8496).
35. Hanzlikova J, Praus P, Baumruk V,. Raman optical activity spectrometer for peptide studies. J Mol Struct 1999; 481: 431 435.
36. Kapitan J, Baumruk V, Kopecky V, Bour P,. Conformational flexibility of L -alanine Zwitterion determines shapes of Raman and Raman optical activity spectral bands. J Phys Chem A 2006; 110: 4689 4696.
37. Bour P,. Computations of the Raman optical activity via the sum-over-states expansions. J Comput Chem 2001; 22: 426 435.
38. Bour P, Baumruk V, Hanzlikova J,. Measurement and calculation of the Raman optical activity of alpha-pinene and trans-pinane. Collect Czech Chem Commun 1997; 62: 1384 1395.
39. Bour P, Sopkova J, Bednarova L, Malon P, Keiderling TA,. Transfer of molecular property tensors in Cartesian coordinates: a new algorithm for simulation of vibrational spectra. J Comput Chem 1997; 18: 646 659.
40. Fric I, Leonteva LI, Malon P, Jost K, Blaha K,. Synthesis and chiroptical properties of heterodetic cyclic hexapeptides related to oxytocin ring moiety. Collect Czech Chem Commun 1980; 45: 1109 1131.
41. Chacko KK, Saenger W,. Topography of cyclodextrin inclusion complexes. 15. Crystal and molecular-structure of the cyclohexaamylose-7.57 water complex, form-Iii4-membered and 6-membered circular hydrogen-bonds. J Am Chem Soc 1981; 103: 1708 1715.