Circular dichroism studies on absolute configuration assignment of peptidomimetics with a terminal chiral 3-arylpropionic acid unit

Tetrahedron Asymmetry

Volumn 17, Issue 17, 2006, Pages 2469-2478

  Frelek, Jadwiga ^a   Fryszkowska, Anna ^b   Kwit, Marcin ^c   Ostaszewski, Ryszard ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLPROPIONIC ACID DERIVATIVE; CARBON; ESTER DERIVATIVE; PEPTIDE DERIVATIVE; PEPTIDOMIMETIC; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; MOLECULAR MODEL; PRIORITY JOURNAL; RELIABILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33750174110     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.08.024     Document Type: Article

References (30)

1. Loughlin W.A., Tyndall J.D.A., Glenn M.P., and Fairlie D.P. Chem. Rev. 104 (2004) 6085
2. Tyndall J.D.A., Pfeiffer B., Abbenante G., and Fairlie D.P. Chem. Rev. 105 (2005) 793
3. Leban J.J., Landavazo A., McDermed J.D., Diliberto Jr. E.J., Jansen M., Stockstill B., and Kull Jr. F.C. J. Med. Chem. 37 (1994) 439
4. Needham J., Kelly M.T., Ishige M., and Andersen R.J. J. Org. Chem. 59 (1994) 2058
5. Tucker T.J., Lumma W.C., Lewis S.D., Gardell S.J., Lucas B.J., Sisko J.T., Lynch J.J., Lyle E.A., Baskin E.P., Woltmann R.F., Appleby S.D., Chen I.-W., Dancheck K.B., Naylor-Olsen A.M., Krueger J.A., Cooper C.M., and Vacca J.P. J. Med. Chem. 40 (1997) 3687
6. Brady S.F., Stauffer K.J., Lumma W.C., Smith G.M., Ramjit H.G., Lewis S.D., Lucas B.J., Gardell S.J., Lyle E.A., Appleby S.D., Cook J.J., Holahan M.A., Stranieri M.T., Lynch Jr. J.J., Lin J.H., Chen I.-W., Vastag K., Naylor-Olsen A.M., and Vacca J.P. J. Med. Chem. 41 (1998) 401
7. Ostaszewski R., Portlock D.E., Fryszkowska A., and Jeziorska K. Pure Appl. Chem. 75 (2003) 413
8. Fryszkowska A., Frelek J., and Ostaszewski R. Tetrahedron 61 (2005) 6064
9. Smith H.E. Circular dichroism of the benzene chromophore. In: Nakanishi K., Berova N., and Woody R.W. (Eds). Circular Dichroism Principles and Applications (2000), VSH, New York 397-429
10. Fryszkowska A., Komar M., Koszelewski D., and Ostaszewski R. Tetrahedron: Asymmetry 16 (2005) 2475
11. Fontana L.P., and Smith H.E. J. Org. Chem. 52 (1987) 3386
12. Pickard S.T., and Smith H.E. J. Am. Chem. Soc. 112 (1990) 5741
13. Koch W., and Holthausen M.C. A Chemist's Guide to Density Functional Theory (2000), Wiley-VCH, Weinheim
14. Adamo C., di Matteo A., and Barone V. From Classical Density Functionals to Adiabatic Connection Methods. The State of the Art. In: Löwdin P.-O. (Ed). Advances in Quantum Chemistry Vol. 36 (1999), Academic Press
15. Geerlings P., De Proft F., and Langenaeker W. Chem. Rev. 103 (2003) 1793
16. Furche F.J. Chem. Phys. 114 (2001) 5982
17. Casida M.E., Jamorski C., Casida K.C., and Salahub D.R. J. Chem. Phys. 108 (1998) 4439
18. Stratmann E.R., Scuseria G.E., and Frisch M.J. J. Chem. Phys. 109 (1998) 8218
19. Gross E.K.U., and Kohn W. Adv. Quantum Chem. 21 (1990) 255
20. Gross E.K.U., Dobson J.F., and Petersilka M. Top. Curr. Chem. 181 (1996) 81
21. Bauernschmitt R., and Ahlrichs R. Chem. Phys. Lett. 256 (1996) 454
22. CaChe Ws Pro 5.0 Fujitsu Ltd.
23. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A.J., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Salvador P., Dannenberg J.J., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 03 (2001), Gaussian, Pittsburgh, PA
24. A recent paper has pointed out the need of using ΔG values rather than ΔE values for calculation of conformer distributions:. Lattanzi A., Viglione R.G., Scettri A., and Zanasi R. J. Phys. Chem. A 108 (2004) 10749
25. Diedrich C., and Grimme S. J. Phys. Chem. A 107 (2003) 2524
26. Anbazhagan M., Reddy T.I., and Rajappa S. J. Chem. Soc., Perkin Trans. 1 11 (1997) 1623
27. Moriniere J.-L., Danree B., Lemoine J., and Guy A. Synth. Commun. 22 (1988) 441
28. Shiina I., Suenaga Y., Nakano M., and Mukaiyama T. Bull. Chem. Soc. Jpn. 73 (2000) 2811
29. Williams M.W., and Young G.T. J. Chem. Soc. (1964) 3701
30. Giordano C., Gallina C., Ottaviano V., Consalvi V., and Scandurra R. Eur. J. Med. Chem. Chim. Ther. 27 (1992) 865