Model systems for flavoenzyme activity. A versatile synthesis of N(3)-alkylated flavins

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4003-4004

  Dutra, Jason K ^a   Cuello, Alejandro O ^a   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLAVOPROTEIN; QUERCETIN; RIBOFLAVIN DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS;

EID: 0031006831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00819-8     Document Type: Article

References (13)

1. Walsh, C. Acc. Chem. Res. 1980, 13, 148-155. Ziegler, D.M. Trends. Pharm. Sci. 1990, 321-324.
2. Walsh, C. Acc. Chem. Res. 1980, 13, 148-155. Ziegler, D.M. Trends. Pharm. Sci. 1990, 321-324.
3. For a recent review of the role of biomedical role of Vitamin 82, and the activity of structural analogs as inhibitors see: Rivlin, R. Chemistry and Biochemistry of the Flavoenzymes, Vol. 1, Müller, F, ed., CRC Press:Boca Raton, 1991, 201-204.
4. For examples see: a) Breinlinger, E.; Rotello, J. Am. Chem. Soc. 1997, 119, 1165-1166.
5. b) Shinkai, S.; Ishikawa, Y.; Shinkai, H.; Tsuno, T.; Makishima, H.; Ueda, K.; Manabe, O. J. Am. Chem. Soc. 1984, 106, 1801-1808.
6. c) Seward, E.M.; Hopkins, R.B.; Sauerer, W.; Tam, S.-W.; Diederich, F. J. Am. Chem. Soc. 1987, 102, 1783-1790.
7. Yoneda, F.; Sakuma, Y.; Ichiba, M.; Shinomura, K. J. Am. Chem. Soc. 1976, 98, 830. For a recent review of flavin syntheses see: Müller, F. Chemistry and Biochemistry of the Flavoenzymes, Vol. 1, Müller, F, ed., CRC Press:Boca Raton, 1991, 4-8.
8. Yoneda, F.; Sakuma, Y.; Ichiba, M.; Shinomura, K. J. Am. Chem. Soc. 1976, 98, 830. For a recent review of flavin syntheses see: Müller, F. Chemistry and Biochemistry of the Flavoenzymes, Vol. 1, Müller, F, ed., CRC Press:Boca Raton, 1991, 4-8.
9. Niemz, A.; Rotello, V. J. Am. Chem. Soc. 1997, 119, 887-892.
10. Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679-671, Mitsunobu, O. Synthesis 1981, 1-28. Hughes, D. Organic Reactions, 1992, 42, 335.
11. Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679-671, Mitsunobu, O. Synthesis 1981, 1-28. Hughes, D. Organic Reactions, 1992, 42, 335.
12. Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679-671, Mitsunobu, O. Synthesis 1981, 1-28. Hughes, D. Organic Reactions, 1992, 42, 335.
13. 3 (0.22 mmol) in dry THF (500 μL) was added the corresponding alcohol 3 (0.6 mmol) then DEAD (0.22 mmol) dropwise at 0° C. The relatively high reagent concentration is required for the success of the reaction. The mixture was stirred at 0°C for two hours, then allowed to proceed at room temperature until the reaction was complete by TLC (2:1 EtOAc:AcCN). The reaction mixture was concentrated in vacuo, then the residue applied to a silica gel flash column, which was eluted with 2:1 EtOAc:Hexane to provide flavins 2a-g as yellow solids.