Mechanism of thyroid hormone biosynthesis. Enzymatic oxidative coupling of 3,5-diiodo-L-tyrosine derivatives

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9211-9214

  Ma, You An ^a   Sih, Charles J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; DEHYDROALANINE; DIIODOTYROSINE; PYRUVIC ACID DERIVATIVE; THYROXINE;

ARTICLE; ENZYME MECHANISM; HORMONE DETERMINATION; HORMONE STRUCTURE; IN VITRO STUDY; MODEL; OXIDATION; THYROID HORMONE SYNTHESIS;

EID: 0033601403     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01655-X     Document Type: Article

References (24)

1. (a) Ekholm, R. Int. Rev. Cytol. 1990, 120, 243-288.
2. (b) Nunez, J. Methods Enzymol. 1984, 107, 476-488.
3. (c) Taurog, A. In Endocrinology; DeGroot, L. J.; Cahill Jr., G. F.; Martini, L.; Nelson, D. H.; Odell, W. D.; Potts Jr., J. T.; Steinberger, E.; Winegrad, A. I., Eds.; Grune & Stratton: New York, 1979; Vol. 1, pp. 331-342.
4. Taurog, A.; Dorris, M. L.; Doerge, D. R. Arch. Biochem. Biophys. 1994, 315, 82-89.
5. (a) Gentile, F.; Di Lauro, R.; Salvatore, G. In Endocrinology, 3rd Ed.; DeGroot, L. J.; Besser, M.; Burger, H. G.; Jameson, J. L.; Loriaux, D. L.; Marshall, J. C.; Odell, W. D.; Potts Jr., J. T.; Rubenstein, A. H., Eds.; W. B. Saunders Company: Philadelphia, 1995; Vol. 1, pp. 517-542.
6. (b) DeGroot, L. J.; Niepomniszcze, H. Metab., Clin. Exp. 1977, 26, 665-718.
7. (a) Oza, V. B.; Salamonczyk, G. M.; Guo, Z. W.; Sih, C. J. J. Am. Chem. Soc. 1997, 119, 11315-11316.
8. (b) Salamonczyk, G. M.; Oza, V. B.; Sih, C. J. Tetrahedron Lett. 1997, 38, 6965-6968.
9. (c) Ogawara, H.; Cahnmann, H. J. Biochim. Biophys. Acta 1972, 257, 328-338.
10. (d) Cahnmann, H. J.; Funakoshi, K. Biochemistry 1970, 9, 90-98.
11. Von Mutzenbecher, P. Z. Physiol. Chem. 1939, 261, 253-256.
12. (a) Dehydroalanine: Gavaret, J. M.; Cahnmann, H. J.; Nunez, J. J. Biol. Chem. 1979, 254, 11218-11222.
13. (b) Alanine: Pitt-Rivers, R. Biochem. J. 1948, 43, 223-231.
14. (c) Hydroxypyruvic acid: Pitt-Rivers, R.; James, A. T. Biochem. J. 1958, 70, 173-176.
15. (d) Serine: Sela, M.; Sarid, S. Nature 1956, 178, 540-541.
16. (e) Pyruvate: Johnson, T. B.; Tewkesbury, L. B. Proc. Natl. Acad. Sci. USA 1942, 28, 73-77.
17. (a) Gavaret, J. M.; Cahnmann, H. J.; Nunez, J. J. Biol. Chem. 1981, 256, 9167-9173.
18. (b) Gavaret, J. M.; Nunez, J.; Cahnmann, H. J. J. Biol. Chem. 1980, 255, 5281-5285.
19. Bell, N. V.; Bowman, W. R.; Coe, P. F.; Turner, A. T.; Whybrow, D. Can. J. Chem. 1997, 75, 873-883.
20. (a) Doerge, D. R.; Taurog, A.; Dorris, M. L. Arch. Biochem. Biophys. 1994, 315, 90-99.
21. (b) Taurog, A.; Dorris, M. L. Arch. Biochem. Biophys. 1992, 296, 239-246.
22. Guo, Z. W.; Salamonczyk, G. M.; Han, K.; Machiya, K.; Sih, C. J. J. Org. Chem. 1997, 62, 6700-6701.
23. -) 607.030, found 607.037.
24. Alexander, N. M.; Nishimoto, M. In Thyroid Research; Stockigt, J. R.; Nagataki, S., Eds.; Australian Academy of Science: Canberra, Australia, 1980; Vol. 8, pp. 117-120.