Three-component condensation leading to β-amino acid diamides: Convergent assembly of β-peptide analogues

Journal of the American Chemical Society

Volumn 126, Issue 42, 2004, Pages 13606-13607

  Oaksmith, Jennifer M ^a   Peters, Ulf ^a   Ganem, Bruce ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID; DIAMIDE; PEPTIDE DERIVATIVE; SOLVENT;

ACYLATION; ARTICLE; CATALYSIS; CRYSTALLIZATION; DEGRADATION KINETICS; DRUG DESIGN; DRUG EFFECT; DRUG SELECTIVITY; DRUG SYNTHESIS; ENERGY YIELD; HYDROGEN BOND; HYDROGENATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; POLYMERIZATION; REDUCTION KINETICS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; TECHNIQUE;

AMIDES; AMINO ACIDS; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 6444223724     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0450152     Document Type: Article

References (19)

1. Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80.
2. Xia, Q.; Ganem, B. Org. Lett. 2002, 4, 1631-1634.
3. (a) Wang, Q.; Xia, Q.; Ganem, B. Tetrahedron Lett. 2003, 44, 6825-6827.
4. (b) Wang, Q.; Ganem, B. Tetrahedron Lett. 2003, 44, 6829-6832.
5. Hook, D. F.; Gessier, F.; Noti, C.; Kast, P.; Seebach, D. ChemBioChem 2004, 5, 691-706.
6. (a) Hayen, A.; Schmitt, M. A.; Ngassa, F. N.; Thomasson, K. A.; Gellman, S. H. Angew. Chem., Int. Ed. 2004, 43, 505-510.
7. (b) De Pol, S.; Zorn, C.; Klein, C. D.; Zerbe, O.; Reiser, O. Angew. Chem., Int. Ed. 2004, 43, 511-514.
8. Huff, J. J. Med. Chem. 1991, 34, 2305-2314.
9. We are grateful to Prof. C. R. Wilcox for these calculations.
10. A single example of this condensation has been reported: Neidlein, R. Arch. Pharm. 1966, 299, 603-605.
11. Hünig, S.; Schaller, R. Angew. Chem., Int. Ed. 1982, 21, 36-49.
12. Prepared by literature methods, (a) Formylation: Duczek, W.; Deutsch, J.; Vieth, S.; Niclas, H.-J. Synthesis 1996, 37-38. (b) Dehydration: Skorna, G.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1977, 16, 259-260.
13. Prepared by literature methods, (a) Formylation: Duczek, W.; Deutsch, J.; Vieth, S.; Niclas, H.-J. Synthesis 1996, 37-38. (b) Dehydration: Skorna, G.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1977, 16, 259-260.
14. Condensations with N-protected (S)-α-amino acids and (S)-α-isocyanoesters afforded 1:1 mixtures of the (S,S,S)- and (S,R,S)-diastereomers. No other diastereomers were detected, indicating that the α-isocyanoesters were configurationally stable.
15. 3, acetic acid, and either cyclohexyl isonitrile or tert-butyl isonitrile following literature protocols: (a) Semple, J. E.; Owens, T. D.; Nguyen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769-2775. (b) Banfi, L.; Guanti, G.; Riva, R. Chem. Commun. 2000, 985-986.
16. 3, acetic acid, and either cyclohexyl isonitrile or tert-butyl isonitrile following literature protocols: (a) Semple, J. E.; Owens, T. D.; Nguyen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769-2775. (b) Banfi, L.; Guanti, G.; Riva, R. Chem. Commun. 2000, 985-986.
17. Methanolysis of peptidyl esters catalyzed by calcium acetate has been observed: Miranda, M. T. M.; Theobaldo, F. C.; Tominaga, M. Int. J. Peptide Prot. Res. 1991, 37, 451-456.
18. 3-OH, but if the PtO2 was first reduced to Pt(0), Sn formed BOC-Phe-OMe in 90% yield after 12 h,
19. Schmitt, M. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2004, 126, 6848-6849.