Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation

Journal of the American Chemical Society

Volumn 127, Issue 39, 2005, Pages 13490-13491

  McFarland, Jesse M ^a   Francis, Matthew B ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HYDROXYL GROUP; IRIDIUM; LYSINE; LYSOZYME; POLYMER; PROTEIN; TRANSITION ELEMENT;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL REACTION; CONCENTRATION RESPONSE; CONJUGATE; ELECTRON TRANSPORT; ELECTROSPRAY MASS SPECTROMETRY; HYDROGENATION; PH; PROTEIN MODIFICATION; PROTEIN STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; ROOM TEMPERATURE; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROSCOPY;

ALKYLATION; AMINO ACID SEQUENCE; CATALYSIS; HYDROGEN; IRIDIUM; PROTEINS;

EID: 25844511741     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054686c     Document Type: Article

References (16)

1. For several recent examples, see: Acc. Chem. Res. 2002, 35 (9).
2. (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc: 2003, 125, 3192.
3. (b) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686.
4. (c) Antos, J. M.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 10256.
5. (d) Ojida, A.; Tsutsumi, H.; Kasagi, N.; Hamachi, I. Tetrahedron Lett. 2005, 46, 3301.
6. For examples on peptides and amino acids, see: (e) Dibowski, H.; Schmidtchen, F. P. Angew. Chem., Int. Ed. 1998, 37, 476.
7. (f) Bong, D. T.; Ghadiri, M. R. Org. Lett. 2001, 3, 2509.
8. Abura, T.; Ogo, S.; Walanabe, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 4149.
9. (a) The parent complex was first described by Ziessel, R. J. Chem. Soc., Chem. Commun. 1988, 1, 16.
10. (b) For a facile synthetic route to these complexes, see: Dadci, L.; Elias, H.; Frey, U.; Hörnig, A.; Koelle, U.; Merbach, A. E.; Paulus, H.; Schneider, J. S. Inorg. Chem. 1995, 34, 306.
11. Ogo, S.; Uehara, K.; Abura, T.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 126, 3020.
12. For an example of alkyne hydration using 2a, see: Ogo, S.; Uehara, K.; Abura, T.; Watanabe, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 726, 16520.
13. 2 reduction: Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Arakawa, H.; Kasuga, K. Organometallics 2004, 23, 1480.
14. See Supporting Information for details and spectra.
15. For examples, see: (a) Breslow, R. Acc. Chem. Res. 2004, 37, 471.
16. See also: (b) Joshi, N. S.; Whitaker, L.; Francis, M. B. J. Am. Chem. Soc. 2004, 726, 15942.