Origin of the stereospecificity in binding hydroxamates of α- and β-phenylalanine methylamide to thermolysin revealed by the X-ray crystallographic study

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 11, 2003, Pages 2421-2426

  Kim, Seung Jun ^a   Kim, Dong H ^b   Park, Jung Dae ^b   Woo, Joo Rang ^a   Jin, Yonghao ^b   Ryu, Seong Eon ^a  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; N FORMYL N HYDROXY ALPHA PHENYLALANINE METHYLAMIDE; N FORMYL N HYDROXY BETA PHENYLALANINE METHYLAMIDE; N HYDROXY DEXTRO PHENYLALANINE METHYLAMIDE; N HYDROXY N FORMYL DEXTRO PHENYLALANINE METHYLAMIDE; N HYDROXY N FORMYLPHENYLALANINE METHYLAMIDE; N HYDROXYPHENYLALANINE METHYLAMIDE; PHENYLALANINE DERIVATIVE; THERMOLYSIN; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; ENANTIOMER; ENZYME INHIBITION; ISOMER; STEREOSPECIFICITY; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0037963122     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00140-8     Document Type: Article

References (19)

1. (a) Matthews B.W. Acc. Chem. Res. 21:1988;333.
2. (b) Fersht A. Enzyme Structure and Mechanism. 2nd ed. 1977;W.H. Freeman & Co. New York. p 418.
3. (a) Ondetti M.A., Rubin B., Cushman D.W. Science. 196:1977;441.
4. (b) Cushman D.W., Cheung H.S., Sabo E.F., Ondetti M.A. Biochemistry. 16:1977;5484.
5. Whittaker M., Floyd C.D., Brown P., Gearing A.J.H. Chem. Rev. 99:1999;2735.
6. Powers, J. C.; Harper, J. W. Inhibitors of Metalloproteases; In Proteinase Inhibitors, Barrett, A. J., Salvesen, G. Ed.; Elsevier: Amsterdam, 1986; pp 219-298.
7. Browner M.F., Smith W.W., Castelhano A.L. Biochemistry. 34:1995;6602.
8. Jin Y., Kim D.H. Tetrahedron: Asymmetry. 8:1997;3699.
9. Jin Y., Kim D.H. Bioorg. Med. Chem. Lett. 8:1998;3515.
10. Feenstra R.W., Stokkinggreef E.H.M., Reichenwein A.M., Lousberg W.B.H., Ottenheijm H.C.J. Tetrahedron. 46:1990;1745.
11. Jahngen E.G.E., Rossomando E.F. Syn. Commun. 12:1982;601.
12. Feder J.A. Biochem. Biophys. Res. Common. 32:1968;326.
13. Cross J.B., Duca J.S., Kaminke J.J., Madison V.S. J. Am. Chem. Soc. 124:2002;11004.
14. Holmes M.A., Matthews B.W. Biochemistry. 20:1981;6912.
15. Holmes M.A., Matthews B.W. J. Mol. Biol. 160:1982;623.
16. Leslie A.G.W. Acta Crystallogr. D55:1999;1696.
17. Collaborative Computational Project Number 4 The CCP4 Suite: Programs for Protein Crystallography, Acta Crystallogr. 1994, D50, 760.
18. Jones T.A., Zou J.Y., Cowan S.W., Kjeldgaard M. Acta Crystallogr. A47:1991;101.
19. Brünger A.T., Adams P.D., Clore G.M., DeLano W.L., Gros P., Grosse-Kunstleve R.W., Jiang J.S., Rice L.M., Simonson T., Warren G.L. Acta Crystallogr. D54:1998;905.