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Side reactions in e...
Side reactions in enzymatic peptide synthesis in organic media : Effects of enzyme, solvent, and substrate concentrations
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- Gololobov, Mikhail Yu (author)
- Lund University
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- Stepanov, Valentin M. (author)
- State Research Institute of Genetics and Selection of Industrial Microorganisms of NRC «Kurchatov Institute»
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- Voyushina, Tatjana L. (author)
- State Research Institute of Genetics and Selection of Industrial Microorganisms of NRC «Kurchatov Institute»
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- Morozova, Irina P. (author)
- State Research Institute of Genetics and Selection of Industrial Microorganisms of NRC «Kurchatov Institute»
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- Adlercreutz, Patrick (author)
- Lund University,Lunds universitet,Bioteknik,Centrum för tillämpade biovetenskaper,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Biotechnology,Center for Applied Life Sciences,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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(creator_code:org_t)
- Elsevier BV, 1994
- 1994
- English 7 s.
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In: Enzyme and Microbial Technology. - : Elsevier BV. - 0141-0229. ; 16:6, s. 522-528
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http://dx.doi.org/10...
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Abstract
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- The progress of enzymatic peptide synthesis catalyzed by α-chymotrypsin and subtilisin from Bacillus subtilis strain 72 (subtilisin 72) in low-water systems was studied. The initial reaction mixture consisted of the solvent, the acyl-group donor (MalAlaAlaPheOMe or ZAlaAlaPheOMe, Mal, maleyl, Z, benzyloxycarbonyl), the nucleophile XaaNH2 (Xaa = Phe, Leu or Ala), and the enzyme adsorbed on porous silica material. All amino acid residues were of the l-configuration. The solvent consisted of acetonitrile, dimethylformamide (DMF), and 4% (v/v) of water. The DMF/acetonitrile ratio was varied between 0 and 1/1. At high concentration of the acyl-group donor and approximately equimolar ratio of the nucleophile and the acyl-group donor, quantitative formation of MalAlaAlaPheXaaNH2 or ZAlaAlaPheXaaNH2 occurred. As a result, a method for the synthesis of polypeptide amides was developed. At low concentration of the acyl-group donor and excess of the nucleophile, the condensation by-products with two and three nucleophile molecules were found in the reaction mixtures. The data obtained provided evidence that organic solvents affected the S'1-specificity of α-chymotrypsin and the Sl-specificity of subtilisin 72, while the Sl-specificity of α-chymotrypsin and the S'l-specificity of subtilisin 72 were not affected. When the DMF content was increased, the rate of the α-chymotrypsin-catalyzed reactions decreased. In contrast to this, an increase in DMF content accelerated the subtilisin 72-catalyzed reactions. Hydrolysis of the acyl-group donor did not occur in the α-chymotrypsin-catalyzed reactions. Significant (up to 50%) formation of MalAlaAlaPheOH was observed a the early stage of the subtilisin 72-catalyzed reactions. Later MalAlaAlaPheOH underwent synthesis.
Subject headings
- TEKNIK OCH TEKNOLOGIER -- Industriell bioteknik -- Biokatalys och enzymteknik (hsv//swe)
- ENGINEERING AND TECHNOLOGY -- Industrial Biotechnology -- Biocatalysis and Enzyme Technology (hsv//eng)
Keyword
- Chymotrypsin
- low-water systems
- polymerization in low-water systems
- subtilisin
Publication and Content Type
- art (subject category)
- ref (subject category)
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