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Organic solvent changes the chymotrypsin specificity with respect to nucleophiles

Gololobov, Mikhail Yu ; Voyushina, Tatyana L. ; Stepanov, Valentin M. and Adlercreutz, Patrick LU (1992) In FEBS Letters 307(3). p.309-312
Abstract

In α-chymotrypsin-catalyzed acyl-transfer reactions in water the specificity of the enzyme (the nucleophile reactivity of amino acid amides) is correlated with the substrate hydrophobicity and increases as the hydrophobicity of the side chain of the amino acid amides is increased. In a low water system (4% H2O) bulky amino acid amides are less efficient nucleophiles. The specificity of α-chymotrypsin towards the amino acid amides in acyl transfer reactions in this case does not depend on the hydrophobicity of the amino acid side chains but correlates with their size. Therefore, different factors can be responsible for the specificity of enzymes in water and in a mainly organic medium.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Low water system, Nucleophile specificity, QSAR, α-Chymotrypsin
in
FEBS Letters
volume
307
issue
3
pages
4 pages
publisher
Wiley-Blackwell
external identifiers
  • pmid:1644186
  • scopus:0026655149
ISSN
0014-5793
DOI
10.1016/0014-5793(92)80702-I
language
English
LU publication?
yes
id
11468db0-d573-4788-b50a-ee08b8c9164c
date added to LUP
2019-06-22 18:40:13
date last changed
2020-01-13 02:05:09
@article{11468db0-d573-4788-b50a-ee08b8c9164c,
  abstract     = {<p>In α-chymotrypsin-catalyzed acyl-transfer reactions in water the specificity of the enzyme (the nucleophile reactivity of amino acid amides) is correlated with the substrate hydrophobicity and increases as the hydrophobicity of the side chain of the amino acid amides is increased. In a low water system (4% H<sub>2</sub>O) bulky amino acid amides are less efficient nucleophiles. The specificity of α-chymotrypsin towards the amino acid amides in acyl transfer reactions in this case does not depend on the hydrophobicity of the amino acid side chains but correlates with their size. Therefore, different factors can be responsible for the specificity of enzymes in water and in a mainly organic medium.</p>},
  author       = {Gololobov, Mikhail Yu and Voyushina, Tatyana L. and Stepanov, Valentin M. and Adlercreutz, Patrick},
  issn         = {0014-5793},
  language     = {eng},
  month        = {08},
  number       = {3},
  pages        = {309--312},
  publisher    = {Wiley-Blackwell},
  series       = {FEBS Letters},
  title        = {Organic solvent changes the chymotrypsin specificity with respect to nucleophiles},
  url          = {http://dx.doi.org/10.1016/0014-5793(92)80702-I},
  doi          = {10.1016/0014-5793(92)80702-I},
  volume       = {307},
  year         = {1992},
}