Utilization of lipases and proteases in preparative organic chemistry
Project/Area Number |
05680514
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Research Category |
Grant-in-Aid for General Scientific Research (C)
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Allocation Type | Single-year Grants |
Research Field |
Bioorganic chemistry
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Research Institution | Konan University |
Principal Investigator |
MIYAZAWA Toshifumi Konan University, Faculty of Scienc, Professor, 理学部, 教授 (50068152)
|
Project Period (FY) |
1993 – 1994
|
Project Status |
Completed (Fiscal Year 1994)
|
Budget Amount *help |
¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1994: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1993: ¥1,200,000 (Direct Cost: ¥1,200,000)
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Keywords | Lipases / Proteases / Primary alcohols / Non-protein amino acids / Carboxylic acids / Enol esters / Optical resolution / Peptide synthesis / 非タンパクアミノ酸 / ジカルボン酸 / 位置選択的反応 |
Research Abstract |
1. About the optical resolution of primary alcohols. Transesterifications between a number of primary alcohols and enol esters in organic solvents were tried using various lipases. Such primary alcohols as 2-phenoxy-1-propanols and 2-phenyl-1-butanol were obtained with high enantioselectivities. The relationship between the structure of the substrate and the enantioselectivity was clarified. 2. About the optical resolution of non-protein amino acids. Hydrolyses of amino acid esters were investigated using various proteases. Thus, proteases from microbial origins such as Bacillus subtilis and Aspergillus oryzae and some thiol proteases were found to be useuful for the resolution of a number of non-protein amino acids. 3. About the optical resolution of carboxylic acids. Transesterifications between the vinyl esters of carboxylic acids, e.g., 2-phenoxypropanoic acids, O-methylmandelic acid, 2-phenylalkanoic acids and 3-chloro-2-phenylacetic acid, and alcohols were investigated using various lipases. Optimal reaction conditions for a high enantioselectivity were revealed and the general applicability of this novel resolution procedure was exemplified. 4. About the regioselective derivatization of dicarboxylic acids. Hydrolyses of N-protected diesters of alpha-amino dicarboxylic acids were tried using various proteases, and it was clarified that hydrolysis takes place almost specifically at the alpha-position. 5. About the synthesis of peptides containing non-protein amino acids. Peptide syntheses in buffer solutions containing organic solvents or in organic solvents containing a small amount of water were investigated using alpha-chymotrypsin. Thus, a number of halogen-substituted phenylalanines were incorporated into peptides. The yields were improved by using as the acyl donor activated esters such as the 2,2,2-trifluoroethyl ester instead of the conventional methyl ester.
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Report
(3 results)
Research Products
(18 results)