Dipeptide surrogates containing asparagine-derived tetrahydropyrimidinones: Structure and amide rotomer stereochemistry of a proline mimic

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5148-5151

  Konopelski, Joseph P ^a   Wei, Yunyang ^a   Olmstead, Marilyn M ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARAGINE; DIPEPTIDE; PROLINE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; ISOMERISM; PROTEIN SECONDARY STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0033063089     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9901790     Document Type: Article

References (17)

1. (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720.
2. (b) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-67.
3. For a recent example, see: Smith, A. B., III; Keenan, T. P.; Holcomb, R. C.; Sprengeler, P. A.; Guzman, M. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1992, 114, 10672-4.
4. Chen, J. K.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 953-69.
5. Konopelski, J. P.; Filonova, L. K.; Olmstead, M. M. J. Am. Chem. Soc. 1997, 119, 4305-6.
6. König, W.; Kernebeck, K. Liebigs Ann. Chem. 1979, 227-47.
7. Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Tetrahedron Lett. 1998, 36, 2937-40.
8. For a review, see: Carpino, L. A. Acc. Chem. Res. 1996, 29, 268-74.
9. Chu, K. S.; Negrete, G. R.; Konopelski, J. P.; Lakner, F. J.; Woo, N.-T.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 1800-12.
10. Juaristi, E.; López-Ruiz, H.; Madrigal, D.; Ramírez-Quirós, Y.; Escalante, J. J. Org. Chem. 1998, 63, 4706-10.
11. Lakner, F. J.; Chu, K. S.; Negrete, G. N.; Konopelski, J. P. Org. Synth. 1995, 73, 201-14.
12. Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727-8.
13. Creighton, T. E. Proteins: Structures and Molecular Properties, 2nd ed.; Freeman: New York, 1993; p 181.
14. Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradón, B.; Hidber, P. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mouriño, A.; Pfammatter, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stucky, G.; Petter, W.; Escalant, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molins, E. Helv. Chim. Acta 1992, 75, 913-34.
15. For a discussion, see: Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512-23.
16. Montelione, G. T.; Arnold, E.; Meinwald, Y. C.; Stimson, E. R.; Denton, J. B.; Huang, S.-G.; Clardy, J.; Scheraga, H. A. J. Am. Chem. Soc. 1984, 106, 7946-58.
17. t are given in the Supporting Information to ref 7.