Imidase catalyzing desymmetric imide hydrolysis forming optically active 3-substituted glutaric acid monoamides for the synthesis of gamma-aminobutyric acid (GABA) analogs
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| 024 | 7 | 0 | |a 10.1007/s00253-015-6812-x |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00253-015-6812-x | ||
| 245 | 0 | 0 | |a Imidase catalyzing desymmetric imide hydrolysis forming optically active 3-substituted glutaric acid monoamides for the synthesis of gamma-aminobutyric acid (GABA) analogs |h [Elektronische Daten] |c [Masutoshi Nojiri, Makoto Hibi, Hiroaki Shizawa, Nobuyuki Horinouchi, Yoshihiko Yasohara, Satomi Takahashi, Jun Ogawa] |
| 520 | 3 | |a The recent use of optically active 3-substituted gamma-aminobutyric acid (GABA) analogs in human therapeutics has identified a need for an efficient, stereoselective method of their synthesis. Here, bacterial strains were screened for enzymes capable of stereospecific hydrolysis of 3-substituted glutarimides to generate (R)-3-substituted glutaric acid monoamides. The bacteria Alcaligenes faecalis NBRC13111 and Burkholderia phytofirmans DSM17436 were discovered to hydrolyze 3-(4-chlorophenyl) glutarimide (CGI) to (R)-3-(4-chlorophenyl) glutaric acid monoamide (CGM) with 98.1% enantiomeric excess (e.e.) and 97.5% e.e., respectively. B. phytofirmans DSM17436 could also hydrolyze 3-isobutyl glutarimide (IBI) to produce (R)-3-isobutyl glutaric acid monoamide (IBM) with 94.9% e.e. BpIH, an imidase, was purified from B. phytofirmans DSM17436 and found to generate (R)-CGM from CGI with specific activity of 0.95U/mg. The amino acid sequence of BpIH had a 75% sequence identity to that of allantoinase from A. faecalis NBRC13111 (AfIH). The purified recombinant BpIH and AfIH catalyzed (R)-selective hydrolysis of CGI and IBI. In addition, a preliminary investigation of the enzymatic properties of BpIH and AfIH revealed that both enzymes were stable in the range of pH 6-10, with an optimal pH of 9.0, stable at temperatures below 40°C, and were not metalloproteins. These results indicate that the use of this class of hydrolase to generate optically active 3-substituted glutaric acid monoamide could simplify the production of specific chiral GABA analogs for drug therapeutics. | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a Imidase |2 nationallicence | |
| 690 | 7 | |a 3-substituted glutarimide |2 nationallicence | |
| 690 | 7 | |a Desymmetrization |2 nationallicence | |
| 690 | 7 | |a Bacterial screening |2 nationallicence | |
| 690 | 7 | |a GABA synthesis |2 nationallicence | |
| 690 | 7 | |a Stereoselective hydrolysis |2 nationallicence | |
| 700 | 1 | |a Nojiri |D Masutoshi |u Biotechnology Development Laboratories, Kaneka Corporation, 1-8 Miyamae, 676-8688, Takasago, Hyogo, Japan |4 aut | |
| 700 | 1 | |a Hibi |D Makoto |u Industrial Microbiology, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | |
| 700 | 1 | |a Shizawa |D Hiroaki |u Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | |
| 700 | 1 | |a Horinouchi |D Nobuyuki |u Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | |
| 700 | 1 | |a Yasohara |D Yoshihiko |u Biotechnology Development Laboratories, Kaneka Corporation, 1-8 Miyamae, 676-8688, Takasago, Hyogo, Japan |4 aut | |
| 700 | 1 | |a Takahashi |D Satomi |u Industrial Microbiology, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | |
| 700 | 1 | |a Ogawa |D Jun |u Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | |
| 773 | 0 | |t Applied Microbiology and Biotechnology |d Springer Berlin Heidelberg |g 99/23(2015-12-01), 9961-9969 |x 0175-7598 |q 99:23<9961 |1 2015 |2 99 |o 253 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00253-015-6812-x |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00253-015-6812-x |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Nojiri |D Masutoshi |u Biotechnology Development Laboratories, Kaneka Corporation, 1-8 Miyamae, 676-8688, Takasago, Hyogo, Japan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Hibi |D Makoto |u Industrial Microbiology, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Shizawa |D Hiroaki |u Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Horinouchi |D Nobuyuki |u Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Yasohara |D Yoshihiko |u Biotechnology Development Laboratories, Kaneka Corporation, 1-8 Miyamae, 676-8688, Takasago, Hyogo, Japan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Takahashi |D Satomi |u Industrial Microbiology, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Ogawa |D Jun |u Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, 606-8502, Sakyo-ku, Kyoto, Japan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Applied Microbiology and Biotechnology |d Springer Berlin Heidelberg |g 99/23(2015-12-01), 9961-9969 |x 0175-7598 |q 99:23<9961 |1 2015 |2 99 |o 253 | ||