基于莽草酸途径微生物合成芳香族化合物及其衍生物的研究进展
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摘要
芳香族化合物是一类重要的天然产物,在自然界中广泛存在,应用于食品、医药、化工等多个领域,主要通过化学合成、植物提取等方式获得。近年来,随着石化资源减少、人类环保意识的加强,微生物合成芳香族化合物及其衍生物成为热点。莽草酸途径合成的芳香族化合物及其衍生物多种多样。现重点综述通过莽草酸途径合成的"达菲"药物前体莽草酸、大宗化学品己二酸前体顺,顺-粘康酸、芳香族氨基酸及其他高附加值芳香族氨基酸衍生物的微生物合成研究进展,为建立生产高附加值化合物的细胞工厂提供参考。
Aromatic compounds are an important class of natural products. They are widely distributed in nature and are used in many fields such as food, medicine, and chemical industry. They are mainly obtained by chemical synthesis and plant extraction. In recent years, with the reduction of petrochemical resources and the enhancement of human environmental awareness, microbial synthesis of aromatic compounds and their derivatives has become a hot spot. The aromatic compounds and their derivatives synthesized by the shikimate pathway are diverse. This review focuses on the advances in the microbial synthesis of shikimic acid(the synthetic precursor of oseltamivir),cis,cis-muconic acid(the precursor of the bulk chemical adipic acid), aromatic amino acids, and other high valueadded aromatic amino acid derivatives synthesized by the shikimate pathway. This review will provide some advice on the establishment of cell factories for the production of high value-added compounds.
Aromatic compounds are an important class of natural products. They are widely distributed in nature and are used in many fields such as food, medicine, and chemical industry. They are mainly obtained by chemical synthesis and plant extraction. In recent years, with the reduction of petrochemical resources and the enhancement of human environmental awareness, microbial synthesis of aromatic compounds and their derivatives has become a hot spot. The aromatic compounds and their derivatives synthesized by the shikimate pathway are diverse. This review focuses on the advances in the microbial synthesis of shikimic acid(the synthetic precursor of oseltamivir),cis,cis-muconic acid(the precursor of the bulk chemical adipic acid), aromatic amino acids, and other high valueadded aromatic amino acid derivatives synthesized by the shikimate pathway. This review will provide some advice on the establishment of cell factories for the production of high value-added compounds.
引文
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[3]Jiang M,Zhang H.Engineering the shikimate pathway for biosynthesis of molecules with pharmaceutical activities in Escherichia coli.Curr Opin Biotech,2016,42:1-6
[4]Tzin V,Galili G,Aharoni A.Shikimate pathway and aromatic amino acid biosynthesis[M]//Encyclopedia of Life Sciences.Chichester:Wiley,2012
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[8]Davis BD.Aromatic biosynthesis.I.The role of shikimic acid.J Biol Chem,1951,191:315-25
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[13]Cui YY,Ling C,Zhang YY,et al.Production of shikimic acid from Escherichia coli through chemically inducible chromosomal evolution and cofactor metabolic engineering.Microb Cell Fact,2014,13:21
[14]Kogure T,Kubota T,Suda M,et al.Metabolic engineering of corynebacterium glutamicum for shikimate overproduction by growth-arrested cell reaction.Metab Eng,2016,38:204-16
[15]Li L,Tu R,Song G,et al.Development of a synthetic3-dehydroshikimate biosensor in Escherichia coli for metabolite monitoring and genetic screening.ACS Synth Biol,2019,8:297-306
[16]Draths KM,Frost JW.Environmentally compatible synthesis of catechol from D-glucose.J Am Chem Soc,1994,116:399-400
[17]Wei N,Draths KM,Frost JW.Benzene-free synthesis of adipic acid.Biotechnol Prog,2002,18:201-11
[18]Sun XX,Lin YH,Huang Q,et al.A novel muconic acid biosynthesis approach by shunting tryptophan biosynthesis via anthranilate.Appl Environ Microb,2013,79:4024-30
[19]Lin Y,Sun X,Yuan Q,et al.Extending shikimate pathway for the production of muconic acid and its precursor salicylic acid in Escherichia coli.Metab Eng,2014,23:62-9
[20]Sun X,Lin Y,Yuan Q,et al.Biological production of muconic acid via a prokaryotic 2,3-dihydroxybenzoic acid decarboxylase.ChemSusChem,2015,7:2478-81
[21]Thompson B,Pugh S,Machas M,et al.Muconic acid production via alternative pathways and a synthetic'metabolic funnel'.ACS Synth Biol,2017,7:565-75
[22]Christian W,Christine B,Sheila W,et al.Biosynthesis of cis,cis-muconic acid and its aromatic precursors,catechol and protocatechuic acid,from renewable feedstocks by Saccharomyces cerevisiae.Appl Environ Microb,2012,78:8421-30
[23]Curran KA,Leavitt JM,Karim AS,et al.Metabolic engineering of muconic acid production in Saccharomyces cerevisiae.Metab Eng,2013,15:55-66
[24]Brückner C,Oreb M,Kunze G,et al.An expanded enzyme toolbox for production of cis,cis-muconic acid and other shikimate pathway derivatives in Saccharomyces cerevisiae.FEMS Yeast Res,2018,18:foy017
[25]Wang S,Bilal M,Zong Y,et al.Development of a plasmid-free biosynthetic pathway for enhanced muconic acid production in Pseudomonas chlororaphis HT66.ACSSynth Biol,2018,7:1131-42
[26]Pop C,Vlase L,Tamas M.Natural resources containing arbutin.Determination of arbutin in the leaves of Bergenia crassifolia(L.)Fritsch.acclimated in Romania.Not Bot Horti Agrobo,2009,37:129-32
[27]Ikuyo H,Ken-Ichi N,Isao K.Structural criteria for depigmenting mechanism of arbutin.Phytother Res,2010,18:475-9
[28]Bang SH,Han SJ,Kim DH.Hydrolysis of arbutin to hydroquinone by human skin bacteria and its effect on antioxidant activity.J Cosmet Dermatol,2010,7:189-93
[29]Lee HJ.Anti-inflammatory effects of arbutin in lipopolysaccharide-stimulated BV2 microglial cells.Inflamma Res,2012,61:817-25
[30]杨祥开,成春燕,欧娜,等.酶法生产α-熊果苷的纯化工艺.华中农业大学学报,2017,36:57-62
[31]姚斌,沈晓兰,潘亚菊.α-熊果苷的研究进展.中国现代应用药学,2005,22:32-3
[32]Nishimura T,Kometani T,Takii H,et al.Purification and some properties ofα-amylase from Bacillus subtilis X-23that glucosylates phenolic compounds such as hydroquinone.J Ferm Bioeng,1994,78:31-6
[33]Kitao S,Sekine H.α-D-glucosyl transfer to phenolic compounds by sucrose phosphorylase from Leuconostoc mesenteroides and production ofα-arbutin.J Agr Chem Soc Japan,1994,58:38
[34]Seo ES,Kang J,Lee JH,et al.Synthesis and characterization of hydroquinone glucoside using Leuconostoc mesenteroides dextransucrase.Enz Micro Tech,2009,45:355-60
[35]Eppink MH,Boeren SA,Vervoort J,et al.Purification and properties of 4-hydr oxybenzoate 1-hydr oxylase(decarboxylating),a novel flavin adenine dinucleotidedependent monooxygenase from Candida parapsilosis CBS604.J Bacteriol,1997,179:6680-7
[36]Arend J,Warzecha H,Hefner T,et al.Utilizing genetically engineered bacteria to produce plant-specific glucoside.Biotechnol Bioeng,2001,76:126-31
[37]Shen X,Wang J,Wang J,et al.High-level de novo biosynthesis of arbutin in engineered Escherichia coli.Metab Eng,2017,42:52-8
[38]Fang MY,Zhang C,Yang S,et al.High crude violacein production from glucose by Escherichia coli engineered with interactive control of tryptophan pathway and violacein biosynthetic pathway.Microb Cell Fact,2015,14:8
[39]Ul-Haq I,Ali S.Microbiological transformation of L-tyrosine to 3,4-dihydroxyphenyl L-alanine(L-dopa)by a mutant strain of Aspergillus oryzae UV-7.Curr Microb,2002,45:88-93
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