Catalytic Hydrolysis of Peptides by Cerium(IV)

Chemistry - A European Journal

Volumn 6, Issue 21, 2000, Pages 3906-3913

  Takarada, Tohru ^a   Yashiro, Mono ^b   Komiyama, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Catalysts; Cerium; Hydrolyses; Lanthanides; Peptides

Indexed keywords

AMINO ACID; CERIUM; DIPEPTIDE; GLYCYLPHENYLALANINE; HISTIDYLGLYCYLPHENYLALANYL HYDROXIDE; LANTHANIDE; OLIGOPEPTIDE; PEPTIDE; PRASEODYMIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; HYDROLYSIS; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

CATALYSIS; CERIUM; DIPEPTIDES; HYDROLYSIS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES; PRASEODYMIUM;

EID: 85046528623     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20001103)6:21<3906::AID-CHEM3906>3.3.CO;2-A     Document Type: Article

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58. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
59. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
60. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; c) M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
61. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; d) B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
62. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
63. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
64. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
65. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
66. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; i) M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
67. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
68. IV is also active for the hydrolysis of DNA: a) Y. Matsumoto, M. Komiyama, Nucleic Acids Symp. Ser. 1992, 27, 33-34; b) T. Shiiba, K. Yonezawa, N. Takeda, Y. Matsumoto, M. Yashiro, M. Komiyama, J. Mol. Catal. 1993, 84, L21-L25; M. Komiyama, T. Kodama, N. Takeda, J. Sumaoka, T. Shiiba, Y. Matsumoto, M. Yashiro, J. Biochem. 1994, 115, 809-810; B. K. Takasaki, J. Chin, J. Am. Chem. Soc. 1994, 116, 1121-1122; e) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama, M. Yashiro, J. Chem. Soc. Perkin Trans. 2 1995, 269-274; f) M. Komiyama, J. Biochem. 1995, 118, 665-670; g) K. Bracken, R. A. Moss, K. G. Ragunathan, J. Am. Chem. Soc. 1997, 119, 9323-9324; h) S. Miyama, H. Asanuma, M. Komiyama, J. Chem. Soc. Perkin Trans. 2 1997, 1685-1688; M. Komiyama, J. Sumaoka, Curr. Opin. Chem. Biol. 1998, 2, 751-757; j) N. H. Williams, B. Takasaki, M. Wall, J. Chin, Acc. Chem. Res. 1999, 32, 485-493; k) P. M. Cullis, E. Snip, J. Am. Chem. Soc. 1999, 121, 6125-6130.
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85. IV, a seven-membered ring is formed. In the hydrolysis of unprotected dipeptides, seven-membered rings are also formed by using the C-terminal carboxylate (see Figure 6).
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88. Of the lanthanide ions, only the Ce has a stable tetravalent state.
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