Unexpected stability of the urea cis-trans isomer in urea-containing model pseudopeptides

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3843-3845

  Semetey, Vincent ^a   Hemmerlin, Christine ^b   Didierjean, Claude ^c   Schaffner, Arnaud Pierre ^a   Giner, Ana Gimenez ^a   Aubry, André ^c   Briand, Jean Paul ^a   Marraud, Michel ^b   Guichard, Gilles ^a  

^a INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^b LAB DE CHIM PHYS MACROMOLECULAIRE   (France)

^c Nancy University CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE; UREA;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; ISOMERISM;

ISOMERISM; MODELS, CHEMICAL; PEPTIDES; UREA;

EID: 0035969628     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0166552     Document Type: Article

References (25)

1. Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296.
2. Fisk, J. D.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 5443-5447.
3. Deshapande, S. V.; Meredith, C. C.; Pasternak, R. A. Acta Crystallogr. 1968, B24, 1396-1397. Zhao, X.; Chang, Y. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634.
4. Deshapande, S. V.; Meredith, C. C.; Pasternak, R. A. Acta Crystallogr. 1968, B24, 1396-1397. Zhao, X.; Chang, Y. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634.
5. Schoonbeeck, F. S.; van Esch, J, H.; Hulst, R.; Kellogg, R. M.; Feringa, B. L. Chem. Eur. J. 2000, 6, 2633-2643.
6. Filleux-Blanchard, M. L.; Durand, A. Org. Magn. Reson. 1971, 3, 187-191.
7. Vegner, R. E.; Chipens, G. I. J. Gen. Chem. USSR (Engl. Transl.) 1975, 45, 431-434. Antsan, Y. E.; Chipens, G. I. Sov. J. Bioorg. Chem. (Engl. Transl.) 1975, 1, 998-1004. Antsan, Y. E.; Makarova, N. A.; Chipens, G. I. Sov. J. Bioorg. Chem. (Engl. Transl.) 1982, 3, 185-190.
8. Vegner, R. E.; Chipens, G. I. J. Gen. Chem. USSR (Engl. Transl.) 1975, 45, 431-434. Antsan, Y. E.; Chipens, G. I. Sov. J. Bioorg. Chem. (Engl. Transl.) 1975, 1, 998-1004. Antsan, Y. E.; Makarova, N. A.; Chipens, G. I. Sov. J. Bioorg. Chem. (Engl. Transl.) 1982, 3, 185-190.
9. Vegner, R. E.; Chipens, G. I. J. Gen. Chem. USSR (Engl. Transl.) 1975, 45, 431-434. Antsan, Y. E.; Chipens, G. I. Sov. J. Bioorg. Chem. (Engl. Transl.) 1975, 1, 998-1004. Antsan, Y. E.; Makarova, N. A.; Chipens, G. I. Sov. J. Bioorg. Chem. (Engl. Transl.) 1982, 3, 185-190.
10. Rodriguez, M.; Dubreuil, P.; Bali, J. P.; Martinez, J. J. Med. Chem. 1987, 30, 758-763.
11. Kawasaki, K.; Maeda, M.; Watanabe, J.; Kaneto, H. Chem. Pharm. Bull. 1988, 36, 1766-1771.
12. Guerlavais, V.; Fehrentz, J.-A.; Deghenghi, R.; Locatelli, V.; Martinez, J. In Peptides 2000; Martinez J., Fehrentz, J.-A., Eds.; EDK: Paris, 2001; pp 649-650.
13. Kemme, A. A.; Shvets, A. E.; Bleidelis, Y. Y.; Antsans, Y. E.; Chipens, G. I. Zh. Struckt. Khim. 1976, 17, 1132-1135.
14. Mishnev, A. F.; Bleidelis, Y. Y.; Antsans, Y. E.; Chipens, G. I. Zh. Struckt. Khim. 1979, 20, 154-157.
15. In a study focused on related geminal bis-ureas as gelator molecules, aggregation behavior has been studied in solution at high concentration, in the gel state, and in the crystal state. See ref 4.
16. 4, and concentrated under reduced pressure to give the acyl azide 6, which was used without further purification. Toluene was added under Ar, and the resulting solution was heated to 65°C under stirring. After the gas evolution had stopped (ca. 10 min), N-hydroxysuccinimide (1 equiv) and pyridine (1 equiv) were added. The mixture was stirred for 5 min at 65 °C and then cooled to room temperature. In all cases, compound 8 crystallized from the toluene solution and was collected by filtration. Recrystallization from toluene afforded pure 8.
17. +.
18. Guichard, G.; Semetey, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705. Guichard, G.; Semetey, V.; Rodriguez, M.; Briand, J. P. Tetrahedron Lett. 2000, 41, 1553-1557.
19. Guichard, G.; Semetey, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705. Guichard, G.; Semetey, V.; Rodriguez, M.; Briand, J. P. Tetrahedron Lett. 2000, 41, 1553-1557.
20. rac-1b rather than (S)-1b gave good quality crystals suitable for single-crystal X-ray structure determination.
21. 2)], 191 parameters.
22. Boussard, G.; Marraud, M. J. Am. Chem. Soc. 1985, 107, 1825-1828.
23. Taylor, R.; Kennard, O. Acta Crystallorg. 1983, B39, 133-138.
24. βI- and βII-turn conformations in model dipeptides with the Pro-Xaa sequences: Aubry, A.; Cung, M. T.; Marraud, M. J. Am. Chem. Soc. 1985, 107, 7640-7647. β-Turn preferences induced by 2.3-methanophenylalanine chirality. Jimenez, A. I.; Cativiela, C.; Aubry, A.; Marraud, M. J. Am. Chem. Soc. 1998, 120, 9452-9459.
25. βI- and βII-turn conformations in model dipeptides with the Pro-Xaa sequences: Aubry, A.; Cung, M. T.; Marraud, M. J. Am. Chem. Soc. 1985, 107, 7640-7647. β-Turn preferences induced by 2.3-methanophenylalanine chirality. Jimenez, A. I.; Cativiela, C.; Aubry, A.; Marraud, M. J. Am. Chem. Soc. 1998, 120, 9452-9459.