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Sản xuất (R)-axit mandelic từ styrene, L-phenylalanine, glycerol hoặc glucose thông qua các biến đổi sinh học theo chuỗi
Tóm tắt
(R)-axit mandelic là một hợp chất hóa học quan trọng trong công nghiệp, đặc biệt được sử dụng để sản xuất kháng sinh. Phương pháp tổng hợp hóa học của nó thường sử dụng cyanide cực độc để sản xuất dạng racemic của nó, sau đó thực hiện tách nhiệt động học với năng suất tối đa 50%. Chúng tôi báo cáo một phương pháp sinh học bền vững và thân thiện với môi trường để sản xuất (R)-axit mandelic từ styrene dễ dàng có sẵn, L-phenylalanine từ nguồn gốc sinh học và các nguyên liệu tái tạo như glycerol và glucose. Một chuỗi enzyme nhân tạo kết hợp epoxid hóa – thủy phân – oxy hóa đôi đã được phát triển để sản xuất (R)-axit mandelic với 1,52 g/L từ styrene với độ tinh khiết > 99% ee. Việc bổ sung quá trình khử amine và khử carboxyl vào chuỗi trên cho phép chuyển đổi trực tiếp L-phenylalanine thành (R)-axit mandelic với 913 mg/L và > 99% ee. Việc biểu hiện chuỗi năm enzyme trong chủng E. coli NST74 sản xuất L-phenylalanine dư thừa dẫn đến tổng hợp trực tiếp (R)-axit mandelic từ glycerol hoặc glucose, đạt 228 hoặc 152 mg/L sản phẩm thông qua lên men. Hơn nữa, việc kết hợp các tế bào E. coli biểu hiện con đường sinh tổng hợp L-phenylalanine với các tế bào E. coli biểu hiện chuỗi enzyme nhân tạo cho phép sản xuất 760 hoặc 455 mg/L (R)-axit mandelic từ glycerol hoặc glucose. Các phương pháp đơn giản, an toàn và thân thiện với môi trường này cho thấy tiềm năng lớn trong việc sản xuất (R)-axit mandelic từ các nguyên liệu tái tạo.
Từ khóa
#(R)-axit mandelic #enzyme nhân tạo #L-phenylalanine #glycerol #glucose #biến đổi sinh học #nguyên liệu tái tạoTài liệu tham khảo
Aston JG, Newkirk JD, Jenkins DM, Dorsky J (2003) Mandelic acid. Org Synth 538:48–48
Becker J, Wittmann C (2015) Advanced biotechnology: metabolically engineered cells for the bio-based production of chemicals and fuels, materials, and health-care products. Angew Chem Int Ed 54(11):3328–3350
Bhatia SK, Mehta PK, Bhatia RK, Bhalla TC (2014) Optimization of arylacetonitrilase production from Alcaligenes sp. MTCC 10675 and its application in mandelic acid synthesis. Appl Microbiol Biotechnol 98:83–94. https://doi.org/10.1007/s00253-013-5288-9
Biermann U, Bornscheuer U, Meier MAR, Metzger JO, Schäfer HJ (2011) Oils and fats as renewable raw materials in chemistry. Angew Chem Int Ed 50(17):3854–3871. https://doi.org/10.1002/anie.201002767
Blacker AJ, Houson IN (2002) Preparation of mandelic acid derivatives. WO Patent 2002066410A1. 29 Aug 2002
Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K (2012) Engineering the third wave of biocatalysis. Nature 485:185–194
Chen X, Yang C, Wang P et al (2017) Stereoselective biotransformation of racemic mandelic acid using immobilized laccase and (S)-mandelate dehydrogenase. Bioresour Bioprocess 4(1):2
Choi YJ, Tribe DE (1982) Continuous production of phenylalanine using an Escherichia coli regulatory mutant. Biotechnol Lett 4(4):223–228. https://doi.org/10.1007/BF00132390
Christensen CH, Rass-Hansen J, Marsden CC, Taarning E, Egeblad K (2008) The renewable chemicals industry. Chemsuschem 1(4):283–289
Corson B, Dodge RA, Harris S, Yeaw J (2003) Mandelic acid. Org Synth 6:58–58
Detzel C, Maas R, Jose J (2011) Autodisplay of nitrilase from Alcaligenes faecalis in E. coli yields a whole cell biocatalyst for the synthesis of enantiomerically pure (R)-mandelic acid. ChemCatChem 3:719–725
Heuts DPHM, Van Hellemond EW, Janssen DB, Fraaije M (2007) Discovery, characterization, and kinetic analysis of an alditol oxidase from Streptomyces coelicolor. J Biol Chem 282(28):20283–20291
Dong J, Fernández-Fueyo E, Hollmann F et al (2018) Biocatalytic oxidation reactions: a chemist’s perspective. Angew Chem, Int Ed 57(30):9238–9261
Gandomkar S, Żądło-Dobrowolska A, Kroutil W (2019) Extending designed linear biocatalytic cascades for organic synthesis. ChemCatChem 11(1):225–243
He YC, Xu JH, Xu Y, Ouyang LM, Pan J (2007) Biocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by a newly isolated nitrilase-producer Alcaligenes sp. ECU0401. Chin Chem Lett 18:677–680. https://doi.org/10.1016/j.cclet.2007.04.034
Jiang W, Tao R, Yang Y et al (2017) Production of (R)-(-)-mandelic acid with nitrilase immobilized on D155 resin modified by L-lysine. Biochem Eng J 127:32–42. https://doi.org/10.1016/j.bej.2017.07.010
Jiang X-P, Lu T-T, Liu C-H et al (2016) Immobilization of dehydrogenase onto epoxy-functionalized nanoparticles for synthesis of (R)-mandelic acid. Int J Biol Macromol 88:9–17
Keasling JD (2010) Manufacturing molecules through metabolic engineering. Science 330:1355–1358
Kinbara K, Sakai K, Hashimoto Y, Nohira H, Saigo K (1996) Design of resolving reagents: p-substituted mandelic acids as resolving reagents for 1-arylalkylamines. Tetrahedron Asymmtry 7:1539–1542. https://doi.org/10.1016/0957-4166(96)00175-9
Lee JW, Na D, Park JM, Lee J, Choi S, Lee SY (2012) Systems metabolic engineering of microorganisms for natural and non-natural chemicals. Nat Chem Biol 8:536–546. https://doi.org/10.1038/nchembio.970
Li G-Y, Huang K-L, Jiang Y-R, Ding P (2007) Production of (R)-mandelic acid by immobilized cells of Saccharomyces cerevisiae on chitosan carrier. Process Biochem 42:1465–1469. https://doi.org/10.1016/j.procbio.2007.06.015
Lukito BR, Sekar BS, Wu S, Li Z (2019a) Whole cell-based cascade biotransformation for the production of (S)-mandelic acid from styrene, L-phenylalanine, glucose, or glycerol. Adv Synth Catal. https://doi.org/10.1002/adsc.201900373
Lukito BR, Wu S, Saw HJJ, Li Z (2019b) One-pot production of natural 2-phenylethanol from L-phenylalanine via cascade biotransformations. ChemCatChem 11(2):831–840. https://doi.org/10.1002/cctc.201801613
Mills J, Schmiegel KK, Shaw WN (1983) Phenethanolamines, compositions containing the same, and method for effecting weight control. US Patent US4391826A. 5 Jul 1983
Nielsen J, Keasling Jay D (2016) Engineering cellular metabolism. Cell 164:1185–1197. https://doi.org/10.1016/j.cell.2016.02.004
Reetz MT (2013) Biocatalysis in organic chemistry and biotechnology: past, present, and future. J Am Chem Soc 135(34):12480–12496. https://doi.org/10.1021/ja405051f
Reifenrath M, Boles E (2018) Engineering of hydroxymandelate synthases and the aromatic amino acid pathway enables de novo biosynthesis of mandelic and 4-hydroxymandelic acid with Saccharomyces cerevisiae. Metab Eng 45:246–254. https://doi.org/10.1016/j.ymben.2018.01.001
Schrittwieser JH, Velikogne S, Hall M, Kroutil W (2018) Artificial biocatalytic linear cascades for preparation of organic molecules. Chem Rev 118(1):270–348. https://doi.org/10.1021/acs.chemrev.7b00033
Sekar BS, Lukito BR, Li Z (2019) Production of natural 2-phenylethanol from glucose or glycerol with coupled Escherichia coli strains expressing L-phenylalanine biosynthesis pathway and artificial biocascades. ACS Sustain Chem Eng 7:12231–12239. https://doi.org/10.1021/acssuschemeng.9b01569
Sun Z, Ning Y, Liu L et al (2011) Metabolic engineering of the L-phenylalanine pathway in Escherichia coli for the production of S- or R-mandelic acid. Microb Cell Fact 10:71. https://doi.org/10.1186/1475-2859-10-71
Surivet J-P, Vatèle J-M (1999) Total synthesis of antitumor Goniothalamus styryllactones. Tetrahedron 55:13011–13028. https://doi.org/10.1016/S0040-4020(99)00794-2
Tuck CO, Pérez E, Horváth IT, Sheldon RA, Poliakoff M (2012) Valorization of biomass: deriving more value from waste. Science 337:695–699. https://doi.org/10.1126/science.1218930
van Hellemond EW, Vermote L, Koolen W et al (2009) Exploring the biocatalytic scope of alditol oxidase from Streptomyces coelicolor. Adv Synth Catal 351(10):1523–1530. https://doi.org/10.1002/adsc.200900176
Vennestrøm PNR, Osmundsen CM, Christensen CH, Taarning E (2011) Beyond petrochemicals: the renewable chemicals industry. Angew Chem, Int Ed 50:10502–10509. https://doi.org/10.1002/anie.201102117
Wang H, Fan H, Sun H, Zhao L, Wei D (2015) Process development for the production of (R)-(-)-mandelic acid by recombinant Escherichia coli cells harboring nitrilase from Burkholderia cenocepacia J2315. Org Process Res Dev 19:2012–2016. https://doi.org/10.1021/acs.oprd.5b00269
Whitesell JK, Reynolds D (1983) Resolution of chiral alcohols with mandelic acid. J Org Chem 48:3548–3551. https://doi.org/10.1021/jo00168a035
Winkler M, Geier M, Hanlon Steven P, Nidetzky B, Glieder A (2018) Human enzymes for organic synthesis. Angew Chem Int Ed. https://doi.org/10.1002/anie.201800678
Woolston BM, Edgar S, Stephanopoulos G (2013) Metabolic engineering: past and future. Annu Rev Chem Biomol Eng 4:259–288. https://doi.org/10.1146/annurev-chembioeng-061312-103312
Wu S, Li A, Chin YS, Li Z (2013) Enantioselective hydrolysis of racemic and meso-epoxides with recombinant Escherichia coli expressing epoxide hydrolase from Sphingomonas sp. HXN-200: preparation of epoxides and vicinal diols in high ee and high concentration. ACS Catalysis 3(4):752–759. https://doi.org/10.1021/cs300804v
Wu S, Li Z (2018) Whole-cell cascade biotransformations for one-pot multistep organic synthesis. ChemCatChem 10(10):2164–2178. https://doi.org/10.1002/cctc.201701669
Wu S, Snajdrova R, Moore JC, Baldenius K, Bornscheuer UT (2020) Biocatalysis: enzymatic synthesis for industrial applications. Angew Chem Int Ed 59:2–34. https://doi.org/10.1002/anie.202006648
Wu S, Zhou Y, Seet D, Li Z (2017) Regio- and stereoselective oxidation of styrene derivatives to arylalkanoic acids via one-pot cascade biotransformations. Adv Synth Catal 359(12):2132–2141. https://doi.org/10.1002/adsc.201700416
Xiao M-T, Huang Y-Y, Shi X-A, Guo Y-H (2005) Bioreduction of phenylglyoxylic acid to R-(-)-mandelic acid by Saccharomyces cerevisiae FD11b. Enzyme Microb Technol 37:589–596. https://doi.org/10.1016/j.enzmictec.2005.02.018
Yutthalekha T, Warakulwit C, Limtrakul J, Kuhn A (2015) Enantioselective recognition of DOPA by mesoporous platinum imprinted with mandelic acid. Electroanalysis 27:2209–2213. https://doi.org/10.1002/elan.201500145
Zhang Z-J, Xu J-H, He Y-C, Ouyang L-M, Liu Y-Y, Imanaka T (2010) Efficient production of (R)-(-)-mandelic acid with highly substrate/product tolerant and enantioselective nitrilase of recombinant Alcaligenes sp. Process Biochem 45:887–891. https://doi.org/10.1016/j.procbio.2010.02.011
Zhimin O, Ma L, Niu Y, Cui J (2017) Preparation of (R)-(-)-mandelic acid by two-step biotransformation of ethyl benzoylformate. Biocatal Biotransfor. https://doi.org/10.1080/10242422.2017.1420063
Zhou Y, Wu S, Li Z (2016) Cascade biocatalysis for sustainable asymmetric synthesis: from biobased L-Phenylalanine to high-value chiral chemicals. Angew Chem, Int Ed 55(38):11647–11650. https://doi.org/10.1002/anie.201606235
Zhou Y, Wu S, Mao J, Li Z (2018) Bioproduction of benzylamine from renewable feedstocks via a nine-step artificial enzyme cascade and engineered metabolic pathways. Chemsuschem 11(13):2221–2228. https://doi.org/10.1002/cssc.201800709