The Primary Specificity of α-Chymotrypsin. Acylated Amino Acid Esters with Normal Alkyl Side Chains

J. Bryan Jones, Toyoki Kunitake, Carl Niemann, George E. Hein

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

The α-chymotrypsin-catalyzed hydrolysis of a series of N-acetyl-L-amino acid esters of the general formula CH3CONHCH[(CH2)nH]CO2CH3, where n=1-6, has been examined. For this series, K0 reaches a minimum and k0 a maximum when n=5. The method of interaction of acylated L-amino acid derivatives with chymo-trypsin is discussed as well as the magnitude of the forces which can be attributed to the side chain. Each additional methylene group up to the optimum number contributes approximately 680-790 cal. to increased substrate binding and 500 cal. toward decreasing the free energy of activation of the rate-determining kinetic step. The data are incorporated into a general correlation between structure and a-chymotrypsin specificity.

Original languageEnglish
Pages (from-to)1777-1781
Number of pages5
JournalJournal of the American Chemical Society
Volume87
Issue number8
DOIs
Publication statusPublished - Jan 1 1965
Externally publishedYes

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Chymotrypsin
Amino acids
Esters
Amino Acids
Trypsin
Free energy
Hydrolysis
Chemical activation
Derivatives
Kinetics
Substrates

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

The Primary Specificity of α-Chymotrypsin. Acylated Amino Acid Esters with Normal Alkyl Side Chains. / Jones, J. Bryan; Kunitake, Toyoki; Niemann, Carl; Hein, George E.

In: Journal of the American Chemical Society, Vol. 87, No. 8, 01.01.1965, p. 1777-1781.

Research output: Contribution to journalArticle

Jones, J. Bryan ; Kunitake, Toyoki ; Niemann, Carl ; Hein, George E. / The Primary Specificity of α-Chymotrypsin. Acylated Amino Acid Esters with Normal Alkyl Side Chains. In: Journal of the American Chemical Society. 1965 ; Vol. 87, No. 8. pp. 1777-1781.
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