(1) GGT阻害剤

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1 (GGT) (glutathione, GSH, -L-Glu-L-Cys-Gly) Cys 1 10 mm GSSG GSH 98% - + H 3 N COO - γ- O H N O N H SH O γ-glu Cys Gly OH - (GGT, EC ) GGT (GSH) GSX - Glu Cys(X)-Gly 1-2) GGT - 1

2 hydrolases transferases Cys-Gly GGT GSH GSX - GGT!-Glu-Cys-Gly + H 2 O Glu + Cys-Gly (hydrolysis) GGT!-Glu-Cys-Gly + Y!-Glu-Y + Cys-Gly (transpeptidation) GGT 20,000 40,000 GGT γ-gtp, γ-gpt 3) GGT GGT GGT GGT GGT GGT 1-3) Cys Cys SH 2

3 Cys Glu, Cys Gly Cys Cys GGT GGT cytoplasm!-gcs!-glu-cys Glu!-Glu-Cys-Gly (GSH) Glu Cys-Gly GS Cys + ATP Gly + ATP!-Glu-Cys-Gly Cys Gly GGT GGT Cys Cys GGT Cys GGT 3

4 GGT X GSX 1-3) GGT GSX X Cys(X)-Gly X [N-Ac-Cys(X)] GGT X GGT GGT GGT GGT GGT GGT GGT GGT GGT - - γ-glutamyl-enz intermediate GGT 4

5 GGT 2) N-terminal nucleophile hydrolase (Ntn-hydrolase) 4) Ntn-hydrolase Ser, Thr, Cys GGT GGT 1 5) COO + O HO-GGT H 3 N P O F 1 F H 3 N COOH O P O O GGT GGT GGT (a) [1] = 0, (b) 0.17, (c) 0.33, (d) 0.5, (e) 0.67, and (f) 1.0 µm. (Inoue, M. et al. Biochemistry 39, 7764 (2000)) 5

6 GGT GGT (Inoue, M. et al. Biochemistry 39, 7764 (2000) ) GGT 165 LC-MS Thr Thr His Tyr Ser Val Asp Asp y 9 y 8 y 7 y 6 y 5 y 4 y 3 y 2 y 1 Lys N Thr Thr391 Lys399 MS/MS y y1-y8 y9 N Thr 6

7 165 N Thr (Thr391) 1 GGT Thr391 p- 2a-d 6) 2d GGT N Thr Thr381 7) GGT X Thr391-8) + H 3 N COO- O P 2 O O - X 2a: X = H 2b: CF 3 2c: Ac 2d: CN GGT acivicin GGT acivicin [(αs,5s)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid] GGT GGT acivicin 2) COO - H + Cl 3 N O N acivicin 2d GGT acivicin GGT N Thr X 7

8 GGT acivicin acivicin GGT glutamine amidotransferase (GAT) 9) GGT GGT GGT GGT acivicin GGT 10) + H 3 N COO- O P O OCH 3 3 3a: X = CH 3 3b: OCH 3 3c: H 3d: Cl X 3e: X = CF 3 3f: CN 3g: NO 2 - COO - COO O + H 3 N P O O O + H 3 N P O O O O O N H COOH CH COO - COO + H 3 N P O - + COO H 3 N P O O O O O COO- CH 3 CH 3 6a 6b 8

9 GGT Typical time-dependent inhibition of E. coli and human GGT by 4 γ-gluamc AMC 9

10 Ki kon kon 3a-g GGT I GGT 3a-g 2a-d X = CF3 2b 3e GGT 3e GGT kon GGT pka GGT 100 3g kon = 35,000 M -1 s -1 acivicin Acivicin GGT kon = 10

11 0.4 M -1 s -1 GGT acivicin GGT Acivicin Cl - HCl pka = a-g 3g acivicin acivicin 300 GGT kon = 4200 M -1 s -1 Cl - pka g 1/8 acivicin 3 GGT pka log kon Brønsted plot Brønsted plots for GGT inactivation GGT 3a-g pka kon Brønsted βlg βlg = -1 11

12 ΔΔG ΔΔG dissociative transition state Thr GGT - 11) GGT Thr X GGT 4, 5 GGT 3f, 3c GGT 4 (kon = 2400 M -1 s -1 ) acivicin 6000 GGT 12

13 GGT 6a 3c 130 6b 150 GGT GGT Brønsted plot 4, 5, 6a GGT 3a-g (pka) GGT log kon pka 4, 5, 6a GGT Brønsted plots for E. coli & human GGT inactivation 13

14 4, 5, 6a 8 GGT 6a 6b GGT Ki 6a , 5, 6a GGT E I complex E I complex Thr 8 C GGT GGT C 14

15 GGT GGT - - Glu - GGT X Cys-Gly GGT X GGT (A) GGT, (B) GGT 15

16 - Cys-Gly GGT Helicocbacter pylori Bacillus subtilis GGT X Cys-Gly - - 8) Thr Ala S- Cys-Gly X 11) Cys-Gly GGT - Cys-Gly GGT Cys-Gly GGT GGT Cys-Gly GGT Cys-Gly 5 Cys-Gly GGT X 16

17 GGT GGT GGT Cys antioxidative enzyme - Cys-Gly O2 O2 -, GGT prooxidantive enzyme Cys-Gly pka Cys-Gly (SH ) N Cys SH Cys-Gly Cys pka 6.4 Fe 3+ Fe 2+ GGT 17

18 GGT GGT GGT Cys Cys-Gly GGT GGT.. GGT GGT prooxidant GGT GGT GGT GGT Cys Cys SH pka - - GGT Cys GGT -. GGT 18

19 GGT GGT GGT GGT GGT GGsTop TM 6a GGT GGT 4, 5, 6a GGT 6a (GGsTop TM ) GGT kon = 51 M -1 s -1 - COO + H 3 N P O O O CH 3 6a GGsTop TM COO GGT acivicin 130 in vivo GGT GGT GGT acivicin glutamine amidotransferase (GAT) acivicin m- GAT GAT 6a - 19

20 GGT GGT GGT 6a GGT GGT a GGsTop TM acivicin GGT GGsTop TM GGsTop TM 1 10 µm 20 µm 1 mm GGsTop TM JST A-STEP HP 1) J. Hiratake, H. Suzuki, K. Fukuyama, K. Wada and H. Kumagai: Handbook of Proteolytic Enzymes, 3rd Ed., Chapter 820, 3714 (2012). 2) N. Taniguchi and Y. Ikeda: Adv. Enzymol. Relat. Areas Mol. Biol., 72, 239 (1998). 3) J. B. Whitfield: Crit. Rev. Clin. Lab. Sci., 38, 263 (2001). 4) J. A. Brannigan, G. Dodson, H. J. Duggleby, P. C. E. Moody, J. L. Smith, 20

21 D. R. Tomchick, A. G. Murzin; Nature, 378, 416 (1995). 5) M. Inoue, J. Hiratake, S. Hideyuki, H. Kumagai, K. Sakata: Biochemistry, 39, 7764 (2000). 6) H. Liyou, J. Hiratake, T. Norihito, H. Suzuki, H. Kumagai, K. Sakata: Bioorg. Med. Chem., 14, 6043 (2006). 7) R. Castonguay, D. Halim, M. Morin, A. Furtos, C. Lherbet, E. Bonneil, P. Thibault, J. W. Keillor: Biochemistry 46, (2007). 8) T. Okada, H. Suzuki, K. Wada, H. Kumagai, K. Fukuyama; Proc. Natl. Acad. Sci. U. S. A., 103, 6471 (2006). 9) P. J. O Dwyer, M. T. Alonso, B. Leyland-Jones: J. Clin. Oncol. 2, 1064 (1984). 10) L. Han, J. Hiratake, A. Kamiyama, K. Sakata: Biochemistry, 46, 1432 (2007). 11) J. W. Keillor, A. Ménard, R. Castonguay, C. Lherbet, and C. Rivard: J. Phys. Org. Chem. 17, 529 (2004). 12) A. L. Morrow, K. Williams, A. Sand, G. Boanca, and J. J. Barycki: Biochemistry 46, (2007). 21

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