311
Views
0
CrossRef citations to date
0
Altmetric
Biochemistry & Molecular Biology

A novel method of producing the key intermediate ASI-2 of ranirestat using a porcine liver esterase (PLE) substitute enzyme

ORCID Icon, &
Pages 1124-1135 | Received 27 Dec 2018, Accepted 01 Feb 2019, Published online: 20 Feb 2019

References

  • Negoro T, Murata M, Ueda S, et al. Novel, highly potent aldose reductase inhibitors: (R)-(−)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3ʹ-pyrrolidine-1,2ʹ,3,5ʹ-tetrone (AS-3201) and its congeners. J Med Chem. 1998;41:4118–4129.
  • Hamada Y, Kitoh R, Raskin P. Crucial role of aldose reductase activity and plasma glucose level in sorbitol accumulation in erythrocytes from diabetic patients. Diabetes. 1991;40:1233–1240.
  • Toyoda F, Tanaka Y, Ota A, et al. Effect of ranirestat, a new aldose reductase inhibitor, on diabetic retinopathy in SDT rats. J Diabetes Res. 2014; article ID 672590. 1–7. doi:10.1155/2014/672590
  • Tanaka D, inventor; Dainippon Sumitomo Pharma Co., Ltd., assignee. 3-Hydrazino-2,5-dioxopyrrolidine-3-carboxylates, process for production of the same, and use of the same. United States patent US 8,003,808 B2. 2011 Aug 23.
  • Tanaka D, Negoro T, inventors; Dainippon Sumitomo Pharma Co., Ltd., assignee. Optically active 3-amino-2,5-dioxopyrrolidine-3-carboxylate, process for production of the compound, and use of the compound. United States patent US 8,058,456 B2. 2011 Nov 15.
  • Kudo Y, Yamada O, inventors; Nissan Chemical Industries, Ltd., Dainippon Sumitomo Pharma Co., Ltd., assignees. Method for producing optically active succinimide compound. United States patent US 7,994,342 B2. 2011 Aug 9.
  • Inagaki T, Yamakawa Y, inventors; Dainippon Sumitomo Pharma Co., Ltd., and Katayama Seiyakusyo Co., Ltd., assignees. Succinic acid diester derivative, process for production thereof, and use of the derivative in the production of pharmaceutical preparation. United States patent US 8,030,486 B2. 2011 Oct 4.
  • Kasai M, Kita S, Ogawa T, et al. inventors; Dainippon Sumitomo Pharma Co., Ltd., and Kyowa Hakko Bio Co., Ltd., assignees. Process for producing optically active succinimide derivatives and intermediates thereof. United States patent US 8,633,001 B2. 2014 Jan 21.
  • Hayashi Y, Onaka H, Itoh N, et al. Cloning of the gene cluster responsible for biosynthesis of KS-505a (longestin), a unique tetraterpenoid. Biosci Biotechnol Biochem. 2007;71:3072–3081.
  • Yamamura ET, Kita S. A novel method of producing the pharmaceutical intermediate (R)-2-chloromandelic acid by bioconversion. Biosci Biotechnol Biochem. 2019;83:309–317.
  • Okazaki R, Kiyota H, Oritani T. Enzymatic resolution of (±)-epoxy-β-cyclogeraniol, a synthetic precursor for abscisic acid analogs. Biosci Biotechnol Biochem. 2000;64:1444–1447.
  • Kanjanavas P, Khuchareontaworn S, Khawsak P, et al. Purification and characterization of organic solvent and detergent tolerant lipase from thermotolerant Bacillus sp. RN2. Int J Mol Sci. 2010;11:3783–3792.
  • Park EY, Sato M, Kojima S. Lipase-catalyzed biodiesel production from waste activated bleaching earth as raw material in a pilot plant. Bioresour Technol. 2008;99:3130–3135.
  • Bornscheuer UT, Kazlauskas RJ. Hydrolases in organic synthesis -regio- and stereoselective biotransformations. 2nd ed. Weinheim: Wiley-VCH; 2006.
  • Faber K. Biotransformations in organic chemistry. 5th ed. Berlin, Heidelberg, New York: Springer; 2004.
  • de Maria PD, Kossmann B, Potgrave N, et al. Improved process for the enantioselective hydrolysis of prochiral diethyl malonates catalyzed by pig liver esterase. Synlett. 2005;11:1746–1748.
  • Lam LKP, Hui RAHF, Jones JB. Enzymes in organic synthesis. 35. Stereoselective pig liver esterase catalyzed hydrolyses of 3-substituted glutarate diesters. Optimization of enantiomeric excess via reaction conditions control. J Org Chem. 1986;51:2047–2050.
  • Bornscheuer U, Hummel A, Böttcher D, et al. inventors; Enzymicals AG, assignee. Isoforms of pig liveresterase. United States patent US 8,304.223 B2. 2012 Nov 6.
  • Seebach D, Eberle M. Enantioselective cleavage of meso-nitrodiol diacetates by an esterase concentrate from fresh pig liver: preparation of useful nitroaliphatic building blocks for EPC syntheses. Chimia (Aarau). 1986;40:315–318.
  • Faber D, Jencks WP. Different forms of pig liver esterase. Arch Biochem Biophys. 1980;203:214–226.
  • Brüsehaber E, Schwiebs A, Schmidt M, et al. Production of pig liver esterase in batch fermentation of E. coli Origami. Appl Microbiol Biotechnol. 2010;86:1337–1344.
  • Böttcher D, Brüsehaber E, Doderer K, et al. Functional expression of the γ-isoenzyme of pig liver carboxyl esterase in Escherichia coli. Appl Microbiol Biotechnol. 2007;73:1282–1289.
  • Lange S, Musidlowska A, Schmidt-Dannert C, et al. Cloning, functional expression, and characterization of recombinant pig liver esterase. Chembiochem. 2001;2:576–582.
  • Menon V, Rao M. Trends in bioconversion of lignocellulose: biofuels, platform chemicals & biorefinery concept. Prog Energy Combust Sci. 2012;38:522–550.
  • Takeuchi M, Kishino S, Park SB, et al. Efficient enzymatic production of hydroxy fatty acids by linoleic acid Δ9 hydratase from Lactobacillus plantarum AKU 1009a. J Appl Microbiol. 2016;120:1282–1288.
  • Yamamura ET. Bioconversion of pyridoxine to pyridoxamine through pyridoxal using a Rhodococcus expression system. J Biosci Bioeng. 2019;127:79–84.
  • Kozono I, Mihara K, Minagawa K, et al. Engineering of the cytochrome P450 monooxygenase system for benzyl maltol hydroxylation. Appl Microbiol Biotechnol. 2017;101:6651–6658.
  • Kato Y, Tsuda T, Asano Y. Nitrile hydratase involved in aldoxime metabolism from Rhodococcus sp. strain YH3-3 purification and characterization. Eur J Biochem. 1999;263:662–670.
  • Sambrook J, Fritsch EF, Maniatis T. Molecular cloning: a laboratory manual. 2nd ed. New York (NY): Cold Spring Laboratory; 1989.
  • Yamamura ET. Construction of Rhodococcus expression vectors and expression of the aminoalcohol dehydrogenase gene in Rhodococcus erythropolis. Biosci Biotechnol Biochem. 2018;82:1396–1403.
  • Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 1970;227:680–685.
  • Altschul SF, Madden TL, Schaffer AA, et al. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res. 1997;25:3389–3402.
  • Obst M, Oppermann-Sanio FB, Luftmann H, et al. Isolation of cyanophycin-degrading bacteria, cloning and characterization of an extracellular cyanophycinase gene (cphE) from Pseudomonas anguilliseptica strain BI. The cphE gene from P. anguilliseptica BI encodes a cyanophycinhydrolyzing enzyme. J Biol Chem. 2002;277:25096–25105.
  • Lapidus A, Goltsman E, Auger S, et al. Extending the Bacillus cereus group genomics to putative food-borne pathogens of different toxicity. Chem Biol Interact. 2008;171:236–249.
  • Johnson SL, Daligault HE, Davenport KW, et al. Complete genome sequences for 35 biothreat assay-relevant bacillus species. Genome Announc. 2015;3:e00151–15.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.