Di-oxanipecotic acids as more stable turn motifs than di-nipecotic acids

Tetrahedron Letters

Volumn 44, Issue 17, 2003, Pages 3447-3450

  Baek, Bong Hyeon ^a   Lee, Myung Ryul ^a   Kim, Kwang Yon ^a   Cho, Ung In ^a   Boo, Doo Wan ^a   Shin, Injae ^a  

^a Yonsei University   (South Korea)

Author keywords

Amino acids and derivatives; Coupling reactions; Hydrogen bonding; Peptide analogues mimetics

Indexed keywords

CHEMICAL COMPOUND; DIMER; NIPECOTIC ACID DERIVATIVE; OXANIPECOTIC ACID; TETRAMER; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0037459869     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00677-4     Document Type: Article

References (24)

1. Yang D., Li B., Ng F.-F., Yan Y.-L., Qu J., Wu Y.-D. J. Org. Chem. 66:2001;7303.
2. Yang D., Qu J., Li W., Zhang Y.-H., Ren Y., Wang D.-P., Wu Y.-D. J. Am. Chem. Soc. 124:2002;12410.
3. Yang D., Zhang Y.-H., Zhu N.-Y. J. Am. Chem. Soc. 124:2002;9966.
4. Shin I., Lee M.-r., Lee J., Jung M., Lee W., Yoon J. J. Org. Chem. 65:2000;7667.
5. Shin J., Lee J. Synlett. 2000;1297.
6. Shin I., Park K. Org. Lett. 4:2002;869.
7. Lee M.-r., Lee J., Shin I. Synlett. 2002;1463.
8. Lee M.-r., Lee J., Baek B.-h., Shin I. Synlett. 2003;325
9. Baek, B.-h.; Lee, M.-r.; Kim, K.-Y.; Cho, U.-I; Boo, D. W.; Shin, I. Org. Lett. 2003, in press
10. Lee, M.-r.; Kim, K.-Y.; Cho, U.-I; Boo, D. W.; Shin, I. Chem. Commun. 2003, in press.
11. For reviews, see: (a) Seebach, D.; Mattews, J. L. Chem. Commun. 1997, 2015; (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173; (c) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893; (d) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
12. For reviews, see: (a) Seebach, D.; Mattews, J. L. Chem. Commun. 1997, 2015; (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173; (c) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893; (d) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
13. For reviews, see: (a) Seebach, D.; Mattews, J. L. Chem. Commun. 1997, 2015; (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173; (c) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893; (d) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
14. For reviews, see: (a) Seebach, D.; Mattews, J. L. Chem. Commun. 1997, 2015; (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173; (c) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893; (d) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
15. Chung Y.J., Christianson L.A., Stanger H.E., Powell D.R., Gellman S.H. J. Am. Chem. Soc. 120:1998;10555.
16. Chung Y.J., Huck B.R., Christianson L.A., Stanger H.E., Krauthäuser S., Powell D.R., Gellman S.H. J. Am. Chem. Soc. 122:2000;3996.
17. Huck B.R., Fisk J.D., Gellman S.H. Org. Lett. 2:2000;2607.
18. Since N-acetylated peptidomimetics possessing di-oxanipecotic acids were sparingly soluble in nonpolar solvents such as methylene chloride and chloroform, which are ideal for examining hydrogen bond formations by FT-IR and NMR, Boc-protected compounds were prepared for structural studies.
19. 4c We assumed that carbonyl of Boc group is a worse hydrogen bond acceptor to C-terminal NH than that of acetyl group and thus only L,(R)-Nip,(S)-Nip,L forms the folded conformation.
20. See Supplementary Material.
21. Maxfield F.R., Leach S.J., Stimson E.R., Powers S.P., Scheraga H.A. Biopolymers. 18:1979;2507.
22. Gardner R.R., Liang G.-B., Gellman S.H. J. Am. Chem. Soc. 121:1999;1806.
23. We also performed DMSO titration and concentration dependence experiments for all the tetramers. See Supplementary Material.
24. Gaussian 98: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; 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.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.