Regioselective hydrolysis of tryptophan-containing peptides promoted by palladium(II) complexes [10]

Journal of the American Chemical Society

Volumn 121, Issue 37, 1999, Pages 8663-8664

  Kaminskaia, Natalia V ^a,b   Johnson, T Wade ^b   Kostić, Nenad M ^b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM COMPLEX; PEPTIDE; TRYPTOPHAN;

CATALYSIS; HYDROLYSIS; LETTER; METAL BINDING; PROTEIN BINDING; PROTEIN DEGRADATION; STEREOCHEMISTRY;

EID: 0033595464     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9840246     Document Type: Letter

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22. 2+ and 3, respectively.
23. Complex 3 is formed regardless of the mole ratio of Pd(II) to N-acetyl-L-tryptophanamide. Concentration of 3 never exceeded the lowest initial concentration of the substrates.
24. 15N HETCOR spectra ruled out the iminol species and deprotonation of the amide nitrogen.
25. 13C resonance of C(3) is at 70.0 ppm.
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29. 3 (Ala) 1.50 d. See also the Supporting Information.
30. 2+. We report average results of several experiments.
31. 1H NMR spectra remain unchanged.
32. Calculated from the initial rate of alanine formation and the known initial concentration of 3.
33. -1, respectively, at 323 K. Initial concentrations of the dipeptides and palladium(II) complexes were 0.10 M each.
34. 2+ over a mixture of Met-, His-, and Trp-containing peptides, upon addition of water only the Trp-containing peptide is cleaved.