Development of a new protein labeling strategy, oxidation labeling. part 1: Preliminary evaluation and synthesis of tautomycin containing a metal coordinating unit

Tetrahedron

Volumn 66, Issue 9, 2010, Pages 1735-1741

  Sydnes, Magne O ^a   Miyazaki, Atsushi ^a   Isobe, Minoru ^a   Ohinata, Hiroshi ^b   Miyazu, Motoi ^b   Takai, Akira ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b ASAHIKAWA MEDICAL COLLEGE   (Japan)

Author keywords

Protein labeling; Protein phosphatase 1 ; Reactive oxygen species (ROS); Tautomycin

Indexed keywords

AMINE; COORDINATION COMPOUND; COPPER ION; HISTIDINE; HYDROGEN PEROXIDE; METAL; OXIME; PHOSPHOPROTEIN PHOSPHATASE 1; PHOSPHOPROTEIN PHOSPHATASE 1GAMMA; REACTIVE OXYGEN METABOLITE; TAUTOMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL LABELING; ENZYME INHIBITION; MOLECULAR STABILITY; OXIDATION; OXIDATION LABELING; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN DETERMINATION; SYNTHESIS;

EID: 75149172980     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.12.036     Document Type: Article

References (60)

1. For reviews regarding photoaffinety labeling, see:
2. Sinz A. Mass Spectrom. Rev. 25 (2006) 663-682
3. Fleming S.A. Tetrahedron 51 (1995) 12479-12520
4. Kotzyba-Hibert F., Kapfer I., and Goeldner M. Angew. Chem., Int. Ed. Engl. 34 (1995) 1296-1312
5. For a recent review regarding fluorescence labeling, see:. Gonçalves M.S.T. Chem. Rev. 109 (2009) 190-212
6. For a review describing radio labeling using iodine, see:. Seevers R.H., and Counsell R.E. Chem. Rev. 82 (1982) 575-590
7. Bode W., and Huber R. Eur. J. Biochem. 204 (1992) 433-451
8. Betz M., Saxena K., and Schwalbe H. Curr. Opin. Chem. Biol. 10 (2006) 219-225
9. Kondo N., Isobe M., Imai K., and Goto T. Tetrahedron Lett. 24 (1983) 925-928
10. Kondo N., Imai K., Isobe M., and Goto T. Tetrahedron Lett. 25 (1984) 3869-3872
11. Kondo N., Isobe M., Imai K., and Goto T. Agric. Biol. Chem. 49 (1985) 71-83
12. Hayashi Y., Nakagawa C.W., Uyakul D., Imai K., Isobe M., and Goto T. Biochem. Cell Biol. 66 (1988) 288-295
13. Hayashi Y., Nakagawa C.W., Mutoh N., Isobe M., and Goto T. Biochem. Cell Biol. 69 (1991) 115-121
14. Hayashi Y., Isobe M., Mutoh N., Nakagawa C.W., and Kawabata M. Methods Enzymol. 205 (1991) 348-358
15. Isobe M., Hayashi Y., Imai K., Nakagawa C.W., Uyakul D., Mutoh N., and Goto T. In: Stillman M.J., Shaw C.F., and Suzuki K.T. (Eds). Metallothionein: Synthesis, Structure and Properties of Metallothioneins, Phytochelatins and Metal-Thiolate Complexes (1992), VCH, New York, NY 227-256
16. Kurahashi T., Miyazaki A., Suwan S., and Isobe M. J. Am. Chem. Soc. 123 (2001) 9268-9278
17. Uchida K., and Kawakishi S. J. Biol. Chem. 269 (1994) 2405-2410
18. Lim J., and Vachet R.W. Anal. Chem. 75 (2003) 1164-1172
19. Xu G., and Chance M.R. Chem. Rev. 107 (2007) 2514-3543
20. Stadtman E.R. Annu. Rev. Biochem. 62 (1993) 797-821
21. Isobe M., Kai H., Kurahashi T., Suwan S., Pitchayawasin-Thapphasaraphong S., Franz T., Tani N., Higashi K., and Nishida H. ChemBioChem 7 (2006) 1590-1598
22. Zhang Z., Barlow J.N., Baldwin J.E., and Schofield C.J. J. Biochemistry 36 (1997) 15999-16007
23. Cao W., and Barany F. J. Biol. Chem. 273 (1998) 33002-33010
24. Hlavaty J.J., Benner J.S., Hornstra L.J., and Schildkraut I. Biochemistry 39 (2000) 3097-3105
25. Hovorka S.W., Williams T.D., and Schöneich C. Anal. Biochem. 300 (2002) 206-211
26. Lim J., and Vachet R.W. Anal. Chem. 76 (2004) 3498-3504
27. Kurono M., Shimomura A., and Isobe M. Tetrahedron 60 (2004) 1773-1780
28. Kurono M., and Isobe M. Chem. Lett. 33 (2004) 452-453
29. Isobe M., Kurono M., Tsuboi K., and Takai A. Chem. Asian J. 2 (2007) 377-385
30. Sydnes M.O., and Isobe M. Tetrahedron 63 (2007) 2593-2603
31. Sydnes M.O., Kuse M., Kurono M., Shimomura A., Ohinata H., Takai A., and Isobe M. Bioorg. Med. Chem. 16 (2008) 1747-1755
32. For a review discussing the interaction of tautomycin and PP1, see: Sydnes, M.O.; Isobe, M. Chem. Asian J., in press, doi:10.1002/asia.200900394.
33. Cheng X.-C., Kihara T., Kusakabe H., Magae J., Kobayashi Y., Fang R.-P., Ni Z.-C., Ko K., Yamaguchi I., and Isono K. J. Antibiot. 40 (1987) 907-909
34. Ubukata M., Cheng X.-C., and Isono K. J. Chem. Soc., Chem. Commun. (1990) 244-246
35. Cheng X.-C., Ubukata M., and Isono K. J. Antibiot. 43 (1990) 809-819
36. Ubukata M., Cheng X.-C., Isobe M., and Isono K. J. Chem. Soc., Perkin Trans. 1 (1993) 617-624
37. For a review regarding tautomycin and other maleic anhydride containing natural products, see:. Chen X., Zheng Y., and Shen Y. Chem. Rev. 107 (2007) 1777-1830
38. For the X-ray cocrystal structure of PP1 and tautomycin, see:. Kelker M.S., Page R., and Peti W. J. Mol. Biol. 385 (2009) 11-21
39. Magae J., Osada H., Fujiki H., Saido T.C., Suzuki K., Nagai K., Yamasaki M., and Isono K. Proc. Jpn. Acad., Ser. B 66 (1990) 209-212
40. MacKintosh C., and Klumpp S. FEBS Lett. 277 (1990) 137-140
41. For a recent review regarding the 3D structure of PP2A, see:. Mumby M. ACS Chem. Biol. 2 (2007) 99-103
42. Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., and Isono K. Bioorg. Med. Chem. Lett. 6 (1996) 3-8
43. Liu W., Sheppeck J.E., Colby D.A., Huang H.-B., and Nairn A.C. Bioorg. Med. Chem. Lett. 13 (2003) 1597-1600
44. For reviews regarding the preparation and use of Pybox, see:
45. Nishiyama H. Chem. Soc. Rev. 36 (2007) 1133-1141
46. Desimoni G., Faita G., and Quadrelli P. Chem. Rev. 103 (2003) 3119-3154
47. Kazi A.B., Jones G.D., and Vicic D.A. Organometallics 24 (2005) 6051-6054
48. Chevallier P., Soutif J.-C., Brosse J.-C., and Rincón-Guerrero A. Eur. Polym. J. 34 (1998) 767-778
49. Néry L., Lefebvre H., and Fradet A. Macromol. Chem. Phys. 204 (2003) 1755-1764
50. Nishiyama H., Soeda N., Naito T., and Motoyama Y. Tetrahedron: Asymmetry 9 (1998) 2865-2869
51. Nishiyama H., Kondo M., Nakamura T., and Itoh K. Organometallics 10 (1991) 500-508
52. Cabrera D.G., Koivisto B.D., and Leigh D.A. Chem. Commun. (2007) 4218-4220
53. Miyazaki A., Sydnes M.O., Isobe M., Ohinata H., Miyazu M., and Takai A. Bioorg. Med. Chem. 17 (2009) 7978-7986
54. Niklas N., Hampel F., Liehr G., Zahl A., and Alsfasser R. Chem.- Eur. J. 7 (2001) 5135-5142
55. Niklas N., Heinemann F.W., Hampel F., Clark T., and Alsfasser R. Inorg. Chem. 43 (2004) 4663-4673
56. Niklas N., and Alsfasser R. Dalton Trans. (2006) 3188-3199
57. For details see TTMDA (1b) was obtained by treating TTM (1a) with base according to our previously reported method. Ref. 12a.
58. Kurono, M. PhD Thesis, submitted to Nagoya University, February 2004.
59. Takai A., and Mieskes G. Biochem. J. 275 (1991) 233-239
60. Kurono M., and Isobe M. Tetrahedron 59 (2003) 9609-9617