Partial sublimation of enantioenriched amino acids at low temperature. Is it coming from the formation of a euatmotic composition1 of the gaseous phase?

Journal of Organic Chemistry

Volumn 78, Issue 20, 2013, Pages 10530-10533

  Tarasevych, Arkadii V ^a,b   Sorochinsky, Alexander E ^b   Kukhar, Valery P ^b   Chollet, Aurélien ^a   Daniellou, Richard ^c   Guillemin, Jean Claude ^a  

^a UNIV RENNES   (France)

^b INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^c UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERIC EXCESS; GASEOUS PHASE; LOW TEMPERATURES;

AMINO ACIDS; ENANTIOMERS; MIXTURES; TEMPERATURE;

SUBLIMATION;

ALANINE; AMINO ACID; LEUCINE; PHENYLALANINE; PROLINE; VALINE;

AMINO ACID COMPOSITION; ARTICLE; CHEMICAL REACTION; ENANTIOMER; GAS; LOW TEMPERATURE; SUBLIMATION REACTION;

AMINO ACID SEQUENCE; AMINO ACIDS; KINETICS; PEPTIDE FRAGMENTS; STEREOISOMERISM; TEMPERATURE;

EID: 84886383734     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4017474     Document Type: Article

References (23)

1. Clark, J. B.; Hastie, J. W.; Kihlborg, L. H. E.; Metselaar, R.; Thackeray, M. M. Pure Appl. Chem. 1994, 66, 577-594
2. Gamsjäger, H.; Lorimer, J. W.; Scharlin, P.; Shaw, D. G. Pure Appl. Chem. 2008, 80, 233-276 and references therein
3. Cintas, P. Angew. Chem., Int. Ed. 2008, 47, 2918-2920
4. Han, J.; Nelson, D. J.; Sorochinsky, A. E.; Soloshonok, V. A. Curr. Org. Synth. 2011, 8, 310-317
5. Garin, D. L.; Greco, D. J. C.; Kelley, L. J. Org. Chem. 1977, 42, 1249-1251
6. Soloshonok, V. A.; Ueki, H.; Yasumoto, M.; Mekala, S.; Hirschi, J. S.; Singleton, D. A. J. Am. Chem. Soc. 2007, 129, 12112-12113
7. Bellec, A.; Guillemin, J.-C. J. Fluorine Chem. 2010, 131, 545-548
8. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Wiley: New York, 1981; pp 159-165.
9. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 179-183.
10. Farina, M. Chem. Commun. 1987, 1121-1122
11. Farina, M.; Silvestro, G. D. Mol. Cryst. Liq. Cryst. 1988, 161, 177-198
12. Bellec, A. Ph.D. Thesis, University of Rennes, 2009; No. 4010.
13. Albrecht, M.; Soloshonok, V. A.; Schrader, L.; Yasumoto, M.; Suhm, M. A. J. Fluorine Chem. 2010, 131, 495-504
14. Fletcher, S. P.; Jagt, R. B. C.; Feringa, B. L. Chem. Commun. 2007, 2578-2580
15. Perry, R. H.; Wu, C.; Nefliu, M.; Cooks, R. G. Chem. Commun. 2007, 1071-1073
16. Bellec, A.; Guillemin, J.-C. Chem. Commun. 2010, 46, 1482-1484
17. An assumption was made that the composition at the euatmotic points should be equal or close to that at the eutonic points measured for aqueous solutions.(16) However, this assumption is erroneous: striking differences simply by changing the solvent or even "tuning" by the addition of achiral substances were observed. Klussmann, M.; Izumi, T.; White, A. J. P.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2007, 129, 7657-7660
18. Blackmond, D. G.; Klussmann, M. Chem. Commun. 2007, 3990-3996
19. Meyerhoffer, W. Ber. Bunsen.-Ges. Phys. Chem. 1904, 37, 2604-2610
20. Yang, P.; Xu, R.; Nanita, S. C.; Cooks, R. G. J. Am. Chem. Soc. 2006, 128, 17074-17086
21. Weissbuch, I.; Lahav, M. Chem. Rev. 2011, 111, 3236-3267
22. Tarasevych, A. V.; Sorochinsky, A. E.; Kukhar, V. P.; Guillemin, J.-C. Origins Life Evol. Biospheres 2013, 43, 129-135
23. Hušek, P. J. Chromatogr. 1991, 552, 289-299