Abstract
Calorimetric measurements were carried out at 25°C on binary and ternary aqueous solutions containing L and D forms fo the following α-aminoacids: tryptophan, cysteine, methionine, phenylalanine, histidine, threonine, and citrulline, which contain both hydrophilic and hydrophobic domains. Differences were found between the values of the homochiral and heterochiral pairwise enthalpic interaction coefficients for tryptophan, cysteine, and methionine. To the contrary, chiral recognition was not detected for phenylalanine, histidine, citrulline, and threonine. The data were interpreted in terms of a “preferential configuration” model. Chiral recognition is detected only when the interactions of the side chains in the homo- and heterochiral configurations are different. Chiral recognition disappears when a competition exists between zwitterion-zwitterion interactions and side chain-side chain interactions. In some cases, such as for citrulline, compensation effects can occur due to thermal contributions from different domains which mask chiral recognition.
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References
G. Barone, G. Castronuovo, P. Del Vecchio, V. Elia, and S. Puzziello,J. Solution Chem. 18, 1105 (1989).
G. Castronuovo, V. Elia, and M. Magliulo,Can. J. Chem. 69, 794 (1991).
G. Barone, G. Castronuovo, V. Elia, and C. Giancola,J. Chermal Anal. 30, 1367 (1985).
G. M. Blackburn, T. H. Lilley, and P. J. Milburn,J. Chem. Soc. Chem. Comm. 299, (1985).
G. Barone, G. Castronuovo, P. Del Vecchio, V. Elia, and C. Giancola,Thermochim. Acta. 122, 105 (1987).
G. Barone, P. Cacace, G. Castronuovo, and V. Elia,J. Solution Chem. 13, 625 (1984).
S. Andini, G. Castronuovo, V. Elia, and F. Velleca,J. Solution Chem., in press.
A. H. Sijpkes and G. Somsen,J. Chem. Soc. Faraday Trans. 86, 1461 (1990).
M. Matsumoto and K. Amaya,Bull. Chem. Soc. Jpn. 56, 2521 (1983).
S. Miyagishi, S. Matsumura, K. Murata, T. Asakawa, and M. Nishida,Bull. Chem. Soc. Jpn. 58, 1019 (1985).
M. T. Cung, M. Marraud, and J. Néel,Biopolymers 15, 2081 (1976).
M. T. Cung, M. Narraud, and J. Néel,Biopolymers 16, 715 (1977).
M. T. Cung, M. Marraud, J. Néel, and A. Aubry,Biopolymers 17, 1149 (1978).
A. H. Sijpkes and G. Somsen,J. Chem. Soc. Faraday Trans. I 85, 2563 (1989).
M. K. Kumaran, G. R. Hedwig, and I. D. Watson,J. Chem. Thermodyn. 14, 93 (1985).
E. J. Cohn and T. J. Edsall,Proteins, Amino Acids and Peptides, (Reinhold, New York, 1943).
G. Castronuovo, V. Elia, C. Giancola, and S. Puzziello,J. Solution Chem. 19, 855 (1990).
C. Cascella, G. Castronuovo, V. Elia, R. Sartorio, and S. Wurzburger,J. Chem. Soc. Faraday Trans. I 85, 3289 (1989).
J. J. Savage and R. H. Wood,J. Solution Chem. 5, 733 (1976).
B. Y. Okamoto, R. H. Wood, and P. T. Thompson,J. Chem. Soc. Faraday Trans I 74, 1990 (1978).
T. E. Leslie and T. H. Lilley,Biopolymers 24, 695 (1985).
G. Perron and J. E. Desnoyers,J. Chem. Thermodyn. 13, 1105 (1981).
C. Jolicoeur and G. Lacroix,Can. J. Chem. 54, 624 (1976).
S. Wurzburger, R. Sartorio, V. Elia, and C. Cascella,J. Chem. Soc. Faraday Trans. 86, 3891 (1990).
C. Cascella, G. Castronuovo, V. Elia, R. Sartorio, and S. Wurzburger,J. Chem. Soc. Faraday Trans. 1 86, 85 (1990).
S. Andini, G. Castronuovo, V. Elia, and L. Fasano,J. Chem. Soc. Faraday Trans. I 86, 3567 (1990).
L. Ambrosone, S. Andini, G. Castronuovo, V. Elia, and G. Guarino,J. Chem. Soc. Faraday Trans. 87, 2989 (1991).
G. Castronuovo, R. P. Dario, and V. Elia,Thermochim. Acta 181, 305 (1991).
G. Castronuovo, R. P. Dario, C. Della Volpe, and V. Elia,Thermochim. Acta 206, 43 (1992).
G. Castronuovo, C. Della Volpe, V. Elia, and G. Scirè,J. Chem. Soc. Faraday Trans. 88, 2667 (1992).
H. L. Friedman and C. V. Krishnan,J. Solution Chem. 2, 119 (1972).
T. H. Lilley, inThe Chemistry and Biochemistry of Aminoacids G. C. Barret ed., (Chapman and Hall-Methuen, London 1989), Chap. 21.
A. K. Mishra and J. C. Ahluwalia,J. Phys. Chem. 88, 86 (1984).
H. E. Kent, T. H. Lilley, P. J. Milburn, M. Bloemendal, and G. Somsen,J. Solution Chem. 14, 101 (1985).
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Castronuovo, G., Elia, V. & Velleca, F. Chiral recognition in aqueous solutions. Preferential configurations of α-aminoacids bearing substituted alkyl chains at 25°C. J Solution Chem 24, 1209–1217 (1995). https://doi.org/10.1007/BF00972829
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DOI: https://doi.org/10.1007/BF00972829