Gas-Phase enantioselectivity of chiral N-Linked peptidoresorc[4]arene isomers toward dipeptides

Journal of Physical Chemistry A

Volumn 113, Issue 52, 2009, Pages 14625-14629

  Botta, Bruno ^a   Fraschetti, Caterina ^a   D'Acquarica, Ilaria ^a   Speranza, Maurizio ^a   Novara, Francesca R ^b   Mattay, Jochen ^c   Letzel, Matthias C ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^c BIELEFELD UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2-BUTYLAMINE; CHIRAL CAVITY; DI-PEPTIDES; DIASTEREOMERIC; DIPEPTIDE; GASPHASE; GUEST EXCHANGE; HOMOCHIRAL; N-LINKED; RELATIVE STABILITIES;

CHEMICAL REACTIONS; ELECTRON TRANSITIONS; FUNCTIONAL GROUPS; ISOMERS; LEAKAGE (FLUID);

ENANTIOSELECTIVITY;

AROMATIC HYDROCARBON; DIPEPTIDE; NITROGEN;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; GAS; ISOMERISM; KINETICS;

AMINO ACID SEQUENCE; DIPEPTIDES; GASES; HYDROCARBONS, AROMATIC; ISOMERISM; KINETICS; NITROGEN; SUBSTRATE SPECIFICITY;

EID: 73949086151     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp904374h     Document Type: Article

References (39)

1. Schneider, H. Angew. Chem., Int. Ed. Engl 1991, 30, 1417.
2. Chemistry: A Chemical Approach to Enzyme Action, 3rd ed.; Springer-Verlag: New York, 1966; p 252.
3. Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. Engl 1999, 38, 2978.
4. Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663.
5. Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. Nature 1996, 383, 60.
6. For recent reviews on gas-phase enantio- and diastereoselectivity, see: (a) Speranza, M. Chirality 2009, 21, 69.
7. (b) Schug, K. A.; Lindner, W. J. Sep. Sci. 2005, 28, 1932.
8. (c) Speranza, M. Int. J. Mass Spectrom. 2004, 232, 277.
9. (d) Speranza, M. Adv. Phys. Org. Chem. 2004, 39, 147.
10. (e) Tao, W. A.; Cooks, R. G. Anal Chem. 2003, 75, 25A.
11. (f) Lebrilla, C. B. Acc. Chem. Res. 2001, 34, 653.
12. (g) Dearden, D. V.; Liang, Y.; Nicoll, J. B.; Kellersberger, K. A. J. Mass Spectrom. 2001, 36, 989.
13. (h) Filippi, A.; Giardini, A.; Piccirillo, S.; Speranza, M. Int. J. Mass Spectrom. 2000, 198, 137.
14. (i) Schalley, C. A. Int. J. Mass Spectrom. 2000, 194, 11.
15. (j) Sawada, M. Mass Spectrom. Rev. 1997, 16, 73.
16. (k) Sawada, M. In Biological Mass Spectrometry: Present and Future; Matsuo, T., Caprioli, R. M., Gross, M. L., Seyama, T., Eds.; Wiley: New York, 1994.
17. (l) Splitter, J. S.; Tureček, F. Applications of Mass Spectrometry to Organic Stereochemistry, VCH Publishers, New York, 1994.
18. (a) Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, U. K., 1998;
19. (b) Gutsche, C. D. Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 2001.
20. (a) Starnes, S. D.; Rudkevich, D. M.; Rebek, J. J. Am. Chem. Soc. 2001, 123, 4659.
21. (b) Lücking, U.; Tucci, F. C.; Rudkevich, D. M.; Rebek, J. J. Am. Chem. Soc. 2000, 122, 8880.
22. (c) Rudkevich, D. M.; Rebek, J. Eur. J. Org. Chem. 1999, 1991.
23. (d) Rudkevich, D. M. Bull Chem. Soc. Jpn. 2002, 75, 393.
24. Cram, D. J.; Cram, J. M. Container Molecules and their Guests, The Royal Society of Chemistry: Cambridge, 1994.
25. (a) Heinz, T.; Rudkevich, D. M.; Rebek, J. Nature 1998, 394, 764.
26. (b) Rudkevich, D. M. in: Calixarenes 2001; Asfari Z., Böhmer V., Harrowfield J., Vicens J. Eds.; Kluwer: Dordrecht The Netherlands, 2001; p 155;
27. (c) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J. Angew. Chem., Int. Ed. 2002, 41, 1488.
28. Botta, B.; Delle Monache, G.; Salvatore, P.; Gasparrini, F.; Villani, C.; Botta, M.; Corelli, F.; Tafi, A.; Gacs-Baitz, E.; Santini, A.; Carvalho, C. F.; Misiti, D. J. Org. Chem. 1997, 62, 932.
29. (a) Botta, B.; Botta, M.; Filippi, A.; Tafi, A.; Delle Monache, G.; Speranza, M. J. Am. Chem. Soc. 2002, 124, 7658.
30. (b) Tafi, A.; Botta, B.; Botta, M.; Delle Monache, G.; Filippi, A.; Speranza, M. Chem.-Eur. J. 2004, 10, 4126.
31. (d) Botta, B.; Subissati, D.; Tafi, A.; Delle Monache, G.; Filippi, A.; Speranza, M. Angew. Chem. Int. Ed. 2004, 43, 4767.
32. (e) Botta, B.; Caporuscio, F.; Subissati, D.; Tafi, A.; Botta, M.; Filippi, A.; Speranza, M. Angew. Chem. Int. Ed. 2006, 45, 2717.
33. (e) Botta, B.; Caporuscio, F.; D' Acquarica, I.; Delle Monache, G.; Subissati, D.; Tafi, A.; Botta, M.; Filippi, A.; Speranza, M. Chem.-Eur. J. 2006, 12, 8096.
34. Botta, B.; Delle Monache, G.; Fraschetti, C.; Nevola, L.; Subissati, D.; Speranza, M. Int. J. Mass Spectrom. 2007, 267, 24.
35. Botta, B.; D'Acquarica, I.; Delle Monache, G.; Subissati, D.; Uccello-Barretta, G.; Mastrini, M.; Nazzi, S.; Speranza, M. J. Org. Chem. 2007, 72, 9283.
36. Su, T. J. Chem. Phys. 1988, 88, 4102-5355.
37. (a) Nold, M. J.; Cerda, B. A.; Wesdemiotis, C. J. Am. Soc. Mass Spectrom. 1999, 10, 1.
38. (b) Pingitore, F.; Polce, M. J.; Wong, P.; Wesdemiotis, C. J. Am. Soc. Mass Spectrom. 2004, 15, 1025.
39. -1; http://webbook.nist.gov). It is plausible that their 1-3 esters display the same GB as well.