Modeling the Catalytic Site of Liver Alcohol Dehydrogenase: Synthesis and Structural Characterization of a [Bis(thioimidazolyl)(pyrazolyl)hydroborato]zinc Complex, [HB(timMe)2pz]ZnI

Inorganic Chemistry

Volumn 36, Issue 25, 1997, Pages 5680-5681

  Kimblin, Clare ^a   Hascall, Tony ^a   Parkin, Gerard ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001411166     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9710871     Document Type: Article

References (30)

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2. (b) Zinc Enzymes; Bertini, I., Luchinat, C., Maret, W., Zeppezauer M., Eds.; Progress in Inorganic Biochemistry and Biophysics, Vol. 1; Birkhäuser: Boston, MA, 1986; Chapters 28-35.
3. (c) Pocker, Y. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Dekker: New York, 1989; Vol. 25, pp 335-358.
4. The oxidation of certain aldehydes is also catalyzed by LADH. See, for example: Olson, L. P.; Luo, J.; Almarsson, O.; Bruice, T. C. Biochemistry 1996, 35, 9782-9791.
5. (a) Vallee, B. L.; Auld, D. S. Acc. Chem. Res. 1993, 26, 543-551.
6. (b) Lipscomb, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375-2433.
7. 4b,c have been shown to bind zinc at their active sites via one histidine and two cysteine residues, (a) Bracey, M. H.; Christiansen, J.; Tovar, P.; Cramer, S. P.; Bartlett, S. G. Biochemistry 1994, 33, 13126-13131. (b) Betts, L.; Xiang, S.; Short, S. A.; Wolfenden, R.; Carter, C. W., Jr. J. Mol. Biol. 1994, 235, 635-656. (c) Xiang, S.; Short, S. A.; Wolfenden, R.; Carter, C. W., Jr. Biochemistry 1995, 34, 4516-4523.
8. 4b,c have been shown to bind zinc at their active sites via one histidine and two cysteine residues, (a) Bracey, M. H.; Christiansen, J.; Tovar, P.; Cramer, S. P.; Bartlett, S. G. Biochemistry 1994, 33, 13126-13131. (b) Betts, L.; Xiang, S.; Short, S. A.; Wolfenden, R.; Carter, C. W., Jr. J. Mol. Biol. 1994, 235, 635-656. (c) Xiang, S.; Short, S. A.; Wolfenden, R.; Carter, C. W., Jr. Biochemistry 1995, 34, 4516-4523.
9. 4b,c have been shown to bind zinc at their active sites via one histidine and two cysteine residues, (a) Bracey, M. H.; Christiansen, J.; Tovar, P.; Cramer, S. P.; Bartlett, S. G. Biochemistry 1994, 33, 13126-13131. (b) Betts, L.; Xiang, S.; Short, S. A.; Wolfenden, R.; Carter, C. W., Jr. J. Mol. Biol. 1994, 235, 635-656. (c) Xiang, S.; Short, S. A.; Wolfenden, R.; Carter, C. W., Jr. Biochemistry 1995, 34, 4516-4523.
10. For example, only one compound containing a tetrahedral zinc center ligated by one nitrogen, one oxygen, and two sulfur donors is listed in the Cambridge Structural Database. See: McCleverty, J. A.; Morrison, N. J.; Spencer, N.; Ashworth, C. C.; Bailey, N. A.; Johnson, M. R.; Smith, J. M. A.; Tabbiner, B. A.; Taylor, C. R. J. Chem. Soc., Dalton Trans. 1980, 1945-1957.
11. (a) Kaptein, B.; Wang-Griffin, L.; Barf, G.; Kellog, R. M. J. Chem. Soc., Chem. Commun. 1987, 1457-1459.
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16. 2] ligands have also been invoked as models for the active site of LADH. See, for example: Anderson, O. P.; la Cour, A.; Findeisen, M.; Hennig, L.; Simonsen, O.; Taylor, L. F.; Toftlund, H. J. Chem. Soc., Dalton Trans. 1997, 111-120.
17. Dance, I. G. Polyhedron 1986, 5, 1037-1104.
18. 4 has been structurally characterized as a tetramer. See ref 8.
19. Several investigations concerned with systems in which the zinc coordination geometry bears little resemblance to the active site of LADH have also advanced our understanding of the mechanism of action of LADH. See, for example: (a) Shoner, S. C.; Humphreys, K. J.; Barnhart, D.; Kovacs, J. A. Inorg. Chem. 1995, 34, 5933-5934. (b) Kimura, E.; Shionoya, M.; Hoshino, A.; Ikeda, T.; Yamada, Y. J. Am. Chem. Soc. 1992, 114, 10134-10137.
20. Several investigations concerned with systems in which the zinc coordination geometry bears little resemblance to the active site of LADH have also advanced our understanding of the mechanism of action of LADH. See, for example: (a) Shoner, S. C.; Humphreys, K. J.; Barnhart, D.; Kovacs, J. A. Inorg. Chem. 1995, 34, 5933-5934. (b) Kimura, E.; Shionoya, M.; Hoshino, A.; Ikeda, T.; Yamada, Y. J. Am. Chem. Soc. 1992, 114, 10134-10137.
21. (c) Engbersen, J. F. J.; Koudijs, A.; van der Plas, H. C. J. Org. Chem. 1990, 55, 3647-3654.
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26. 2(S)] fragment.
27. 4with excess methimazole. See: Garner, M.; Reglinski, J.; Cassidy, I.; Spicer, M. D.; Kennedy, A. R. J. Chem. Soc., Chem. Commun. 1996, 1975-1976.
28. 3, Z = 4.
29. CNAD is an isosteric C-glycosidic analogue of NADH containing a neutral pyridine ring which is a potent inhibitor of LADH. See: Li, H.; Hallows, W. H.; Punzi, J. S.; Pankiewicz, K. W.; Watanabe, K. A.; Goldstein, B. M. Biochemistry 1994, 33, 11734-11744.
30. The mean value is 1.88[6] Å.