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ChemBioChem

Volumn 13, Issue 12, 2012, Pages 1818-1825

Mushroom Tyrosinase Oxidizes Tyrosine-Rich Sequences to Allow Selective Protein Functionalization

(2) Long, Marcus J C a Hedstrom, Lizbeth a

a BRANDEIS UNIVERSITY (United States)

Author keywords

Cleavage; Crosslinking; Labeling; Protein derivatization; Quinones

Indexed keywords

2 QUINONE; ALANINE DERIVATIVE; BESTHORN REAGENT; CY5 HYDRAZIDE; HEMAGGLUTININ; HYDRAZIDE DERIVATIVE; MONOPHENOL MONOOXYGENASE; NUCLEOPHILE; QUINONE DERIVATIVE; REAGENT; TYROSINE; TYROSINE RICH PROTEIN; TYROSYLPROLYLTYROSYLASPARTYLVALYLPROLYLASPARTYLTYROSYLALANINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; CATALYSIS; COMPLEX FORMATION; CONTROLLED STUDY; DENATURING GRADIENT GEL ELECTROPHORESIS; EXPRESSED SEQUENCE TAG; LABELING INDEX; MUSHROOM; NONHUMAN; OXIDATION REDUCTION REACTION; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN CLEAVAGE; PROTEIN CROSS LINKING; PROTEIN DEGRADATION; PROTEIN FUNCTION;

AGARICALES; BIOCATALYSIS; CARBOCYANINES; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME INHIBITORS; ESCHERICHIA COLI; FUNGAL PROTEINS; HEMAGGLUTININS; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION; PEPTIDES; QUINONES; RECOMBINANT FUSION PROTEINS; TETRAHYDROFOLATE DEHYDROGENASE;

BASIDIOMYCOTA;

EID: 84864760486 PISSN: 14394227 EISSN: 14397633 Source Type: Journal
DOI: 10.1002/cbic.201100792 Document Type: Article

Times cited : (25)

References (48)

1
- 0034709379
- L. Wang, T. J. Magliery, D. R. Liu, P. G. Schultz, J. Am. Chem. Soc. 2000, 122, 5010-5011.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 5010-5011
- Wang, L.¹ Magliery, T.J.² Liu, D.R.³ Schultz, P.G.⁴

2
- 0032499752
- T. W. Muir, D. Sondhi, P. A. Cole, Proc. Natl. Acad. Sci. USA 1998, 95, 6705-6710.
- (1998) Proc. Natl. Acad. Sci. USA , vol.95 , pp. 6705-6710
- Muir, T.W.¹ Sondhi, D.² Cole, P.A.³

3
- 0021891885
- E. T. Kaiser, D. S. Lawrence, S. E. Rokita, Annu. Rev. Biochem. 1985, 54, 565-595.
- (1985) Annu. Rev. Biochem , vol.54 , pp. 565-595
- Kaiser, E.T.¹ Lawrence, D.S.² Rokita, S.E.³

4
- 0023489014
- H. J. Levine, E. T. Kaiser, J. Am. Chem. Soc. 1978, 100, 7670; D. Hilbert, E. T. Kaiser, Biotechnol. Genet. Eng. Rev. 1987, 5, 297.
- (1987) J. Am. Chem. Soc. 1978, 100, 7670; , , Biotechnol. Genet. Eng. Rev , vol.5 , pp. 297
- Levine, H.J.¹ Kaiser, E.T.² Hilbert, D.³ Kaiser, E.T.⁴

5
- 0014430392
- K. Neet, A. Nanci, D. E. Koshland, J. Biol. Chem. 1968, 243, 6392.
- (1968) J. Biol. Chem , vol.243 , pp. 6392
- Neet, K.¹ Nanci, A.² Koshland, D.E.³

6
- 0015245066
- D. F. Schmidt, F. H. Westheimer, Biochemistry 1971, 10, 1249.
- (1971) Biochemistry , vol.10 , pp. 1249
- Schmidt, D.F.¹ Westheimer, F.H.²

7
- 79961009205
- J. Alam, T. H. Keller, T.-P. Loh, Chem. Commun. 2011, 47, 9066-9068.
- (2011) Chem. Commun. , vol.47 , pp. 9066-9068
- Alam, J.¹ Keller, T.H.² Loh, T.-P.³

8
- 4143096987
- J. M. Antos, M. B. Francis, J. Am. Chem. Soc. 2004, 126, 10256.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 10256
- Antos, J.M.¹ Francis, M.B.²

9
- 0034282387
- P. A. Zuk, L. A. Elferink, J. Biol. Chem. 2000, 275, 26754-26764.
- (2000) J. Biol. Chem , vol.275 , pp. 26754-26764
- Zuk, P.A.¹ Elferink, L.A.²

10
- 48049092838
- G. V. Los, L. P. EnCell, M. G. McDougall, N. Karassha, C. Zimprich, M. G. Wood, R. Learish, R. F. Ohana, D. Simpson, J. Mendez, K. Zimmerman, P. Otto, G. Vidugris, J. Zhu, A. Darzins, D. H. Klaubert, R. F. Bulleit, K. V. Wood, ACS Chem. Biol. 2008, 3, 373-382.
- (2008) ACS Chem. Biol. , vol.3 , pp. 373-382
- Los, G.V.¹ EnCell, L.P.² McDougall, M.G.³ Karassha, N.⁴ Zimprich, C.⁵ Wood, M.G.⁶ Learish, R.⁷ Ohana, R.F.⁸ Simpson, D.⁹ Mendez, J.¹⁰ Zimmerman, K.¹¹ Otto, P.¹² Vidugris, G.¹³ Zhu, J.¹⁴ Darzins, A.¹⁵ Klaubert, D.H.¹⁶ Bulleit, R.F.¹⁷ Wood, K.V.¹⁸

11
- 33646755397
- M. A. Jongsma, R. H. Litjens, Proteomics 2006, 6, 2650.
- (2006) Proteomics , vol.6 , pp. 2650
- Jongsma, M.A.¹ Litjens, R.H.²

12
- 33747880302
- J. M. Gilmore, R. A. Scheck, A. P. Esser-Kahn, N. S. Joshi, M. B. Francis, Angew. Chem. 2006, 118, 5433; Angew. Chem. Int. Ed. 2006, 45, 5307.
- (2006) Angew. Chem. 2006, 118, 5433; Angew. Chem. Int. Ed. , vol.45 , pp. 5307
- Gilmore, J.M.¹ Scheck, R.A.² Esser-Kahn, A.P.³ Joshi, N.S.⁴ Francis, M.B.⁵

13
- 33646038598
- For Q-tag see
- For Q-tag see: C.-W. Lin, A. Y. Ting, J. Am. Chem. Soc. 2006, 128, 4542-4543; For PRIME, see: C. Uttamapinant, K. A. White, H. Baruah, S. Thompson, M. Fernández-Suárez, S. Puthenveetil, A. Y. Ting, Proc. Natl. Acad. Sci. USA 2010, 107, 10914-10919.
- (2010) J. Am. Chem. Soc. 2006, 128, 4542-4543; For PRIME, see: , , , , , , , Proc. Natl. Acad. Sci. USA , vol.107 , pp. 10914-10919
- Lin, C.-W.¹ Ting, A.Y.² Uttamapinant, C.³ White, K.A.⁴ Baruah, H.⁵ Thompson, S.⁶ Fernández-Suárez, M.⁷ Puthenveetil, S.⁸ Ting, A.Y.⁹

14
- 27644508250
- J. Yim, P. D. Straight, S. D. McLoughlin, Z. Zhou, A. Lin, D. E. Golan, N. L. Kelleher, R. Kolter, C. T. Walsh, Proc. Natl. Acad. Sci. USA 2005, 102, 15815-15820; J. Yin, A. J. Lin, D. E. Golan, C. T. Walsh, Nat. Protoc. 2006, 1, 280-285.
- (2006) Proc. Natl. Acad. Sci. USA 2005, 102, 15815-15820; , , , , Nat. Protoc. , vol.1 , pp. 280-285
- Yim, J.¹ Straight, P.D.² McLoughlin, S.D.³ Zhou, Z.⁴ Lin, A.⁵ Golan, D.E.⁶ Kelleher, N.L.⁷ Kolter, R.⁸ Walsh, C.T.⁹ Yin, J.¹⁰ Lin, A.J.¹¹ Golan, D.E.¹² Walsh, C.T.¹³

15
- 84864743975
- The Enzymes XIII, 3rd ed., Eds.: D. Boyer), Academic Press, New York
- P. D. Boyer in The Enzymes XIII, 3rd ed., (Eds.: D. Boyer), Academic Press, New York, 1976. For iodohistidine, see: I. Covelli, I. Wolff, J. Biol. Chem. 1966, 241, 4444-4451.
- (1976) J. Biol. Chem , vol.241 , pp. 4444-4451
- Boyer, P.D.¹ Covelli, I.² Wolff, I.³

16
- 0013888072
- J. Wolff, I. Covelli, Biochemistry 1966, 5, 867-871.
- (1966) Biochemistry , vol.5 , pp. 867-871
- Wolff, J.¹ Covelli, I.²

17
- 0014970952
- J. Williams, J. M. Lowe, Biochem. J. 1971, 121, 203-209.
- (1971) Biochem. J , vol.121 , pp. 203-209
- Williams, J.¹ Lowe, J.M.²

18
- 0025076071
- H. Yamada, T. Yamashita, H. Domoto, T. Imoto, J. Biol. Chem. 1990, 108, 432-440.
- (1990) J. Biol. Chem , vol.108 , pp. 432-440
- Yamada, H.¹ Yamashita, T.² Domoto, H.³ Imoto, T.⁴

19
- 77949546659
- E. Baslé, N. Joubert, M. Pucheault, Chem. Biol. 2010, 17, 213-227.
- (2010) Chem. Biol , vol.17 , pp. 213-227
- Baslé, E.¹ Joubert, N.² Pucheault, M.³

20
- 84864756836
- For the addition of cysteins to o-quinones, see
- For the addition of cysteins to o-quinones, see: D. E. Slaughter, R. P. Hanzlik, Chem. Res. Toxicol. 1991, 4, 349; for the addition of lipoic acid, see: K. Tsuji-Naito, T. Hatani, T. Okada, T. Tehara, Biochem. Biophys. Res. Commun. 2006, 343, 15-20. For radical addition to the 1, 2-dione moiety, see: T. Yamaguchi, M. Fujita, Angew. Chem. 2008, 120, 2097-2099; Angew. Chem. Int. Ed. 2008, 47, 2067-2069.
- (2008) Chem. Res. Toxicol. 1991, 4, 349; for the addition of lipoic acid, see: Biochem. Biophys. Res. Commun. 2006, 343, 15-20. For radical addition to the 1,2-dione moiety, see: , , Angew. Chem. 2008, 120, 2097-2099; Angew. Chem. Int. Ed. , vol.47 , pp. 2067-2069
- Slaughter, D.E.¹ Hanzlik, R.P.² Tsuji-Naito, K.³ Hatani, T.⁴ Okada, T.⁵ Tehara, T.⁶ Yamaguchi, T.⁷ Fujita, M.⁸

21
- 0016638983
- G. Agrup, B. Falck, B. M. Kennedy, H. Rorsman, A. M. Rosengren, E. Rosengren, Acta Derm.-Venereol. 1975, 55, 1-3.
- (1975) Acta Derm.-Venereol , vol.55 , pp. 1-3
- Agrup, G.¹ Falck, B.² Kennedy, B.M.³ Rorsman, H.⁴ Rosengren, A.M.⁵ Rosengren, E.⁶

22
- 55449084520
- S. B. Ferreira, C. R. Kaiser, V. F. Ferreira, Synlett 2008, 17, 2625-2628.
- (2008) Synlett , vol.17 , pp. 2625-2628
- Ferreira, S.B.¹ Kaiser, C.R.² Ferreira, V.F.³

23
- 0039520341
- S. W. Weidman, E. T. Kaiser, J. Am. Chem. Soc. 1966, 88, 5820-5827.
- (1966) J. Am. Chem. Soc , vol.88 , pp. 5820-5827
- Weidman, S.W.¹ Kaiser, E.T.²

24
- 84996026241
- L. Malaprade, Bull. Chem. Soc. Fr. 1934, 3, 833.
- (1934) Bull. Chem. Soc. Fr , vol.3 , pp. 833
- Malaprade, L.¹

25
- 0003904322
- Academic Press, San Diego
- G. Prota in Melanins and Melanogenesis, Academic Press, San Diego, 1992.
- (1992) Melanins and Melanogenesis
- Prota, G.¹

26
- 0021213448
- S. Ito, T. Kato, K. Shinpo, K. Fujita, Biochem. J. 1984, 222, 407-411.
- (1984) Biochem. J , vol.222 , pp. 407-411
- Ito, S.¹ Kato, T.² Shinpo, K.³ Fujita, K.⁴

27
- 0035914097
- A. Napolitano, P. Di Donato, G. Prota, J. Org. Chem. 2001, 66, 6958-6966.
- (2001) J. Org. Chem. , vol.66 , pp. 6958-6966
- Napolitano, A.¹ Di Donato, P.² Prota, G.³

28
- 0016638983
- G. Agrup, B. Falck, B. M. Kennedy, H. Rorsman, A. M. Rosengren, E. Rosengren, Acta Derm.-Venereol. 1975, 55, 1-3.
- (1975) Acta Derm.-Venereol. , vol.55 , pp. 1-3
- Agrup, G.¹ Falck, B.² Kennedy, B.M.³ Rorsman, H.⁴ Rosengren, A.M.⁵ Rosengren, E.⁶

29
- 0031991394
- V. Kahn, B.-N. Shalom, Pigment Cell Res. 1998, 11, 24-33.
- (1998) Pigment Cell Res. , vol.11 , pp. 24-33
- Kahn, V.¹ Shalom, B.-N.²

30
- 0022498770
- K. Marumo, J. H. Waite, Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. 1986, 872, 98-103.
- (1986) Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. , vol.872 , pp. 98-103
- Marumo, K.¹ Waite, J.H.²

31
- 0014047283
- J. G. Cory, E. Frieden, Biochemistry 1967, 6, 116-120; and J. G. Cory, E. Frieden, Biochemistry 1967, 6, 121-126.
- (1967) Biochemistry 1967, 6, 116-120; and , , Biochemistry , vol.6 , pp. 121-126
- Cory, J.G.¹ Frieden, E.² Cory, J.G.³ Frieden, E.⁴

32
- 0035527709
- S. Takasaki, S. Kawakishi, M. Murata, S. Homma, Lebensm.-Wiss. Technol. 2001, 24, 507-512.
- (2001) Lebensm.-Wiss. Technol. , vol.24 , pp. 507-512
- Takasaki, S.¹ Kawakishi, S.² Murata, M.³ Homma, S.⁴

33
- 78649451634
- M. Fairhead, L. Thony-Meyer, J. Biotechnol. 2010, 150, 546-551. For the effects of pH and addition of caffeic acid on crosslinking, see: C. Thalmann, T. Lötzbeyer, Eur. Food Res. Technol. 2002, 214, 276-281.
- (2002) J. Biotechnol. 2010, 150, 546-551. For the effects of pH and addition of caffeic acid on crosslinking, see: , , Eur. Food Res. Technol. , vol.214 , pp. 276-281
- Fairhead, M.¹ Thony-Meyer, L.² Thalmann, C.³ Lötzbeyer, T.⁴

34
- 0014047283
- J. G. Cory, E. Frieden, Biochemistry 1967, 6, 121-126.
- (1967) Biochemistry , vol.6 , pp. 121-126
- Cory, J.G.¹ Frieden, E.²

35
- 37349070966
- M. L. Mattinen, R. Lantto, E. Selinheimo, K. Kruus, J. Buchert, J. Biotechnol. 2008, 133, 395-400.
- (2008) J. Biotechnol. , vol.133 , pp. 395-400
- Mattinen, M.L.¹ Lantto, R.² Selinheimo, E.³ Kruus, K.⁴ Buchert, J.⁵

36
- 0030591651
- L. F. Povirik, Mutat. Res. 1996, 355, 71-89.
- (1996) Mutat. Res. , vol.355 , pp. 71-89
- Povirik, L.F.¹

37
- 0002554067
- A. B. Lerner, T. B. Fitzpatrick, Physiol. Rev. 1950, 30, 91-126.
- (1950) Physiol. Rev. , vol.30 , pp. 91-126
- Lerner, A.B.¹ Fitzpatrick, T.B.²

38
- 46149130180
- R. F. Boyer, P. D. Mascotti, B. E. Schori, Phytochemistry 1986, 25, 1281-1283.
- (1986) Phytochemistry , vol.25 , pp. 1281-1283
- Boyer, R.F.¹ Mascotti, P.D.² Schori, B.E.³

39
- 0002554067
- A. B. Lerner, T. B. Fitzpatrick, Physiol. Rev. 1950, 30, 91-126.
- (1950) Physiol. Rev. , vol.30 , pp. 91-126
- Lerner, A.B.¹ Fitzpatrick, T.B.²

40
- 0027491065
- G. M. Jacobsohn, R. Iskandar, M. K. Jacobsohn, Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. 1993, 1202, 317-324.
- (1993) Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. , vol.1202 , pp. 317-324
- Jacobsohn, G.M.¹ Iskandar, R.² Jacobsohn, M.K.³

41
- 0027183423
- E. R. Stadtman, Annu. Rev. Biochem. 1993, 62, 797-821.
- (1993) Annu. Rev. Biochem. , vol.62 , pp. 797-821
- Stadtman, E.R.¹

42
- 0026028299
- L. M. Rzepecki, T. Nagafuchi, J. H. Waite, Arch. Biochem. Biophys. 1991, 285, 17-26.
- (1991) Arch. Biochem. Biophys. , vol.285 , pp. 17-26
- Rzepecki, L.M.¹ Nagafuchi, T.² Waite, J.H.³

43
- 84864756823
- See 2000, 7, 697-708 and J. Agric. Food Chem.
- See: D. A. Fancy, C. Denison, K. Kim, Y. Xie, T. Holdeman, F. Amini, T. Kodadek, Chem. Biol. 2000, 7, 697-708 and W. H. Heijnis, P. A. Wierenga, W. J. H. van Berkel, H. Gruppen, J. Agric. Food Chem. 2010, 58, 5692-5697.
- (2010) Chem. Biol , vol.58 , pp. 5692-5697
- Fancy, D.A.¹ Denison, C.² Kim, K.³ Xie, Y.⁴ Holdeman, T.⁵ Amini, F.⁶ Kodadek, T.⁷ Heijnis, W.H.⁸ Wierenga, P.A.⁹ van Berkel, W.J.H.¹⁰ Gruppen, H.¹¹

44
- 0033596327
- K. Kim, D. A. Fancy, D. Carney, T. Kodadek, J. Am. Chem. Soc. 1999, 121, 11896-11897.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 11896-11897
- Kim, K.¹ Fancy, D.A.² Carney, D.³ Kodadek, T.⁴

45
- 84872218356
- For polymerization through the o-diphenol/o-quinone reaction, see, for a critical account.
- For polymerization through the o-diphenol/o-quinone reaction, see: F. Solano, V. J. Hearing, J. C. García-Borrón, Neurotoxic. Res. 1999, 1, 153-169. Quinone polymerization is often assumed to be the end point of quinones generated in water, but see M. Sugumaran, V. Semensi, H. Dali, W. Mitchell, Bioorg. Chem. 1989, 17, 86-95 for a critical account.
- (1989) Neurotoxic. Res. 1999, 1, 153-169. Quinone polymerization is often assumed to be the end point of quinones generated in water, but see , , , , Bioorg. Chem. , vol.17 , pp. 86-95
- Solano, F.¹ Hearing, V.J.² García-Borrón, J.C.³ Sugumaran, M.⁴ Semensi, V.⁵ Dali, H.⁶ Mitchell, W.⁷

46
- 77955169394
- I. Kaganman, Nat. Methods 2010, 7, 584.
- (2010) Nat. Methods , vol.7 , pp. 584
- Kaganman, I.¹

47
- 83255185003
- I. González-Santoyo, A. Córdoba-Aguilar, Entomol. Exp. Appl. 2012, 142, 1-16.
- (2012) Entomol. Exp. Appl. , vol.142 , pp. 1-16
- González-Santoyo, I.¹ Córdoba-Aguilar, A.²

48
- 57749209855
- Y. S. Baek, Y. B. Ryu, M. J. Curtis-Long, T. J. Ha, R. Rengasamy, M. S. Yang, K. H. Park, Bioorg. Med. Chem. 2009, 17, 35-41.
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 35-41
- Baek, Y.S.¹ Ryu, Y.B.² Curtis-Long, M.J.³ Ha, T.J.⁴ Rengasamy, R.⁵ Yang, M.S.⁶ Park, K.H.⁷

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