Chemoselective alkylation of N-alkylaminooxy-containing peptides

Organic Letters

Volumn 8, Issue 16, 2006, Pages 3529-3532

  Carrasco, Michael R ^a   Silva, Oscar ^a   Rawls, Katherine A ^a   Sweeney, Marisol S ^a   Lombardo, Adria A ^a  

^a SANTA CLARA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYSTEINE; PEPTIDE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION; SYNTHESIS;

ALKYLATION; AMINO ACIDS; CYSTEINE; GLYCOSYLATION; MOLECULAR STRUCTURE; PEPTIDES;

EID: 33747260259     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061289d     Document Type: Article

References (15)

1. (a) Peri, F.; Dumy, P.; Mutter, M. Tetrahedron 1998, 54, 12269-12278.
2. (b) Carrasco, M. R.; Nguyen, M. J.; Burnell, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729.
3. (c) Peri, F.; Venturini, S.; Nicotra, F. In Peptides 2002: Proceedings of the 27th European Peptide Symposium, Aug 31-Sep 6, 2002, Sorrento, Italy; Benedetti, E., Pedone, C., Eds.; Edizioni Ziino: Napoli, Italy, 2002; pp 252-253.
4. (d) Carrasco, M. R.; Brown, R. T. J. Org. Chem. 2003, 68, 8853-8858.
5. (e) Filira, F.; Biondi, B.; Biondi, L.; Giannini, E.; Gobbo, M.; Negri, L.; Rocchi, R. Org. Biomol. Chem. 2003, 1, 3059-3063.
6. (f) Matsubara, N.; Oiwa, K.; Hohsaka, T.; Sadamoto, R.; Niikura, K.; Fukuhara, N.; Takimoto, A.; Kondo, H.; Nishimura, S.-I. Chem. Eur. J. 2005, 11, 6974-6981.
7. For non-peptide examples, see: (a) Peri, F.; Deutman, A.; La Ferla, B.; Nicotra, F. Chem. Commun. 2002, 1504-1505.
8. (b) Peri, F.; Jiménez-Barbero, J.; García-Aparicio, V.; Tvaroška, I.; Nicotra, F. Chem. Eur. J. 2004, 10, 1433-1444.
9. (c) Langenhan, J. M.; Peters, N. R.; Guzei, I. A.; Hoffmann, F. M.; Thorson, J. S. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12305-12310.
10. Bark, S. J.; Schmid, S.; Hahn, K. M. J. Am. Chem. Soc. 2000, 122, 3567-3573
11. Schnölzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Pept. Protein Res. 1992, 40, 180-193.
12. (a) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
13. (b) Carrasco, M. R.; Brown, R. T.; Doan, V. H.; Kandel, S. M.; Lee, F. C. Biopolymers (Peptide Science) 2006, 84, 414-420.
14. The two peaks flanking 6 in the bottom trace were identified by ESI-MS as hydroxyacetyl Val-OMe and acetoxyacetyl Val-OMe, which result from background reactions of the bromide with the buffer and were seen in a control reaction where 4 was omitted. For the chromatograph of the control reaction of 5 with bromoacetylated Val-OMe, see the Supporting Information.
15. 2, 11, confirmed these background alkylations. See the Supporting Information.