Asymmetric enone epoxidation by short solid-phase bound peptides: Further evidence for catalyst helicity and catalytic activity of individual peptide strands

Biopolymers - Peptide Science Section

Volumn 84, Issue 1, 2006, Pages 90-96

  Berkessel, Albrecht ^a   Koch, Burkhard ^a   Toniolo, Claudio ^b   Rainaldi, Mario ^b   Broxterman, Quirinus B ^c   Kaptein, Bernard ^c  

^a UNIVERSITY OF COLOGNE   (Germany)

^b UNIVERSITY OF PADOVA   (Italy)

^c DSM RESEARCH   (Netherlands)

Author keywords

C methyl L leucine; Enones; Epoxidation; Hydrogen Peroxide; Nonlinear Effect; Peptide catalyst

Indexed keywords

CATALYST ACTIVITY; COMPOSITION; HYDROGEN PEROXIDE; POLYPEPTIDES;

CΑ-METHYL-L-LEUCINE; ENONES; EPOXIDATION; NONLINEAR EFFECT; PEPTIDE CATALYST;

KETONES;

CHALCONE; ENONE DERIVATIVE; HYDROGEN PEROXIDE; KETONE DERIVATIVE; LEUCINE; PEPTIDE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; CATALYSIS; CATALYST; ENANTIOMER; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTEIN CONFORMATION; REACTION ANALYSIS; SOLID; STRUCTURE ANALYSIS; SYNTHESIS;

CATALYSIS; CHALCONE; EPOXY COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM;

EID: 33644598465     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/bip.20413     Document Type: Article

References (20)

1. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis, Wiley-VCH: Weinheim, 2005; chap X.2.
2. Juliá, S.; Guixer, J.; Masana, J.; Rocas, J.; Colonna, S.; Annuziata, R.; Molinari, H. J Chem Soc, Perkin Trans 1 1982, 1317-1324.
3. Juliá, S.; Masana, J.; Vega, J. C. Angew Chem Int Ed Engl 1980, 19, 929-930.
4. Bentley, P. A.; Kroutil, W.; Littlechild, J. A.; Roberts, S, M. Chirality 1997, 9, 198-202.
5. Lasterra-Sanchéz, M. E.; Roberts, S. M. J Chem Soc, Perkin Trans 1 1995, 1467-1468.
6. Flood, R. W.; Geller, T. P.; Petty, S. A.; Roberts, S. M.; Skidmore, J.; Volk, M. Org Lett 2001, 3, 683-686.
7. Bentley, P. A.; Cappi, M. W.; Flood, R. W.; Roberts, S. M.; Smith, J. A. Tetrahedron Lett 1998, 39, 9297-9300.
8. Takagi, R.; Shiraki, A.; Manabe, T.; Kjima, S.; Ohkata, K. Chem Lett 2000, 366-367.
9. Berkessel, A.; Gasch, N.; Glaubitz, K.; Koch, C. Org Lett 2001, 3, 3839-3842.
10. (a) Carrea, G.; Colonna, S.; Meek, A. D.; Ottolina, G.; Roberts, S. M. Chem Commun 2004, 1412-1413.
11. (b) Kelly, D. R.; Caroff, E.; Rood, R. W.; Heal, W.; Roberts, S. M. Chem Commun 2004, 2016-2017.
12. (c) Kelly, D. R.; Roberts, S. M. Chem Commun 2004, 2018-2020.
13. Rainaldi, M.; Lancelot, N.; Elbayed, K.; Raya, J.; Piotto, M.; Briand, J.-P.; Kaptein, B.; Broxterman, Q. B.; Berkessel, A.; Formaggio, F.; Toniolo, C.; Bianco, A. Org Biomol Chem 2003, 1, 1835-1837.
14. Girard, C.; Kagan, H. B. Angew Chem Int Ed 1998, 37, 2922-2959.
15. Rainaldi, M. Ph.D. thesis, University of Padova, 2003.
16. Watson, J. D.; Milner-White, E. J. J Mol Biol 2002, 315, 171-182.
17. Watson, J. D.; Milner-White, E. J. J Mol. Biol 2002, 315, 183-191.
18. Page, M.; Williams, A. Organic and Bio-organic Mechanisms; Longman: Singapore, 1997.
19. Marquart, M.; Walter, J.; Deisenhofer, J.; Bode, W.; Huber, R. Acta Crystallogr B 1983, 39, 48CM90.
20. Madder, A.; Farcy, N.; Hosten, N. G. C.; De Muynck, H.; De Clercq, P. J.; Barry, J.; Davis, A. P. Eur J Org Chem 1999, 2787-2791.