Abstraction of deuterium from dideuteroglycine by aryl radical: A model for 1,4-benzene diradical reactions with proteins

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4227-4230

  Braslau, Rebecca ^a   Anderson, Marc O ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amino acids and derivatives; Diynes; Labelling; Radicals and radical reactions

Indexed keywords

BENZENE DERIVATIVE; DEUTERIUM; RADICAL;

ARTICLE; DRUG SYNTHESIS; HYDROGEN BOND; NONHUMAN; PHOTOLYSIS; PROTEIN PROTEIN INTERACTION; PROTON TRANSPORT; REACTION ANALYSIS; RESIDUE ANALYSIS;

EID: 0032508093     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00791-6     Document Type: Article

References (17)

1. 1. For leading references, see: a. Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591-5606.
2. b. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. H. Tetrahedron 1996, 52, 6453-6518.
3. 2. a. Zein, N.; Casazza, A. M.; Doyle, T. W.; Leet, J. E.; Schroeder, D. R.; Solomon, W.; Nadler, S. G. Proc. Natl. Acad. Sci. USA 1993, 90, 8009-8012.
4. b. Zein, N.; Reiss, P.; Bernatowicz, M.; Bolgar, M. Chem. & Bio. 1995, 2, 451-455.
5. 3. Rauk, A.; Yu, D.; Armstrong, D. A. J. Am. Chem. Soc. 1997, 119, 208-217.
6. 4. For a review on amino acid radicals, see: Easton, C. J. Chem. Rev. 1997, 97, 53-82.
7. 5. For aryl radical cleavage of DNA, see: Jebaratnam, D. J.; Kugabalasooriar, S.; Chen, H.; Aray, D. P. Tetrahedron Lett. 1995, 36, 3123-3126.
8. 6. Logan, C. F.; Chen, P. J. Am. Chem. Soc. 1996, 118, 2113-2114.
9. 7. Schottelius, M. J.; Chen, P. J. Am. Chem. Soc. 1996, 118, 4896-4903.
10. 8. Li, R. M.; Smith, R. L.; Kenttamaa, H. I. J. Am. Chem. Soc. 1996, 118, 5056-5061.
11. 9. Wenthold, P. G.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes, in press.
12. 10. Wenthold, P. G.; Squires, R. R. J. Am. Chem. Soc. 1994, 116, 6401-6412.
13. 11. Blomquist, A. T.; Hiscock, B. F.; Harpp, D. N. J. Org. Chem. 1966, 31, 338-339.
14. 12. Braslau, R.; Burrill, L. C.; Siano, M.; Naik, N.; Howden, R. K.; Mahal, L. K. Macromolecules 1997, 30, 6445-6450.
15. 13. The identity of the water soluble by-products is under investigation.
16. 3; δ = 7.65 ppm).
17. 15. Polar reactivity as observed by Myers with allene-ene-ynes is not a possibility with monoradicals: Myers, A. G.; Dragovich, P. S.; Kuo, E. Y. J. Am. Chem. Soc. 1992, 114, 9369-9386.