Catalytic Hydrolysis of Peptides by Cerium(IV)

Tohru Takarada, Mono Yashiro, Makoto Komiyama

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

Oligopeptides are efficiently hydrolyzed by CeIV to the corresponding amino acids under mild conditions. The pseudo first-order rate constants for the hydrolysis of H-Gly-Phe-OH and H-Gly-Gly-OH at pH 7.0 and 50°C are 3.5 × 10-1 and 2.8 × 10-1 h-1, with [Ce(NH4)2(NO3)6]0 = 10 mM (the half-lives are 2.0 and 2.5 h). The catalytic activity of the CeIV is far greater than those of other lanthanide ions and nonlanthanide ions. No oxidative cleavage was observed under the reaction conditions. Catalytic turnover of the CeIV was also evidenced. The hydrolysis is fast especially when the substrates have no metal-coordinating side chains. Tripeptides and tetrapeptides are hydrolyzed at the similar rates as the dipeptides. In the hydrolysis of tripeptides, the amide linkage near the N-terminus is preferentially hydrolyzed. Neither the N-carbobenzyloxy derivative nor the amide of H-Gly-Phe-OH is hydrolyzed to a measurable extent, showing that both the terminal amino group and the carboxylate are coordinated to the CeIV ion. This complexation is further confirmed by 1H NMR spectroscopy. The CeIV ion is therefore one of the most active catalysts for peptide hydrolysis.

Original languageEnglish
Pages (from-to)3906-3913
Number of pages8
JournalChemistry - A European Journal
Volume6
Issue number21
DOIs
Publication statusPublished - Nov 3 2000
Externally publishedYes

Fingerprint

Cerium
Peptides
Hydrolysis
Ions
Amides
Lanthanoid Series Elements
Oligopeptides
Dipeptides
Rare earth elements
Complexation
Nuclear magnetic resonance spectroscopy
Amino acids
Rate constants
Catalyst activity
Metals
Derivatives
Amino Acids
Catalysts
Substrates

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Catalytic Hydrolysis of Peptides by Cerium(IV). / Takarada, Tohru; Yashiro, Mono; Komiyama, Makoto.

In: Chemistry - A European Journal, Vol. 6, No. 21, 03.11.2000, p. 3906-3913.

Research output: Contribution to journalArticle

Takarada, Tohru ; Yashiro, Mono ; Komiyama, Makoto. / Catalytic Hydrolysis of Peptides by Cerium(IV). In: Chemistry - A European Journal. 2000 ; Vol. 6, No. 21. pp. 3906-3913.
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