生物制造不同立体构型2,3-丁二醇:合成机理与实现方法

催化学报 , 2013, 34(2): 351-360. doi: 10.3724/SP.J.1088.2013.20737

生物制造不同立体构型2,3-丁二醇:合成机理与实现方法

沈梦秋 ^1, , 纪晓俊 ^2, , 聂志奎 ^3, , 夏志芳 ^4, , 杨晗 ^5, , 黄和 ^6,

1.南京工业大学生物与制药工程学院,江苏南京211816

2.南京工业大学生物与制药工程学院,江苏南京211816

3.南京工业大学生物与制药工程学院,江苏南京211816

4.南京工业大学生物与制药工程学院,江苏南京211816

5.南京工业大学生物与制药工程学院,江苏南京211816

6.南京工业大学生物与制药工程学院,江苏南京211816;南京工业大学材料化学工程国家重点实验室,江苏南京210009

基金项目: 国家杰出青年科学基金(21225626) the Key Project of Jiangsu Natural Science Foundation(BK2011031) 国家高技术研究发展计划(863计划,2011AA02A207) the National Key Basic Research and Development Program of China(973 Program,2011CBA00807) the National High Technology Research and Development Program of China(863 Program,2011AA02A207) the Priority Academic Program Development of Jiangsu Higher Education Institutions.国家自然科学基金(21006049) the Program for Changjiang Scholars and Innovative Research Team in University(IRT1066) the National Natural Science Foundation of China(21006049) 长江学者和创新团队发展计划(IRT1066) the National Science Foundation for Distinguished Young Scholars of China(21225626) 国家重点基础研究发展计划(973计划,2011CBA00807) 江苏省自然科学基金重点项目(BK2011031) 江苏高校优势学科建设工程资助项目

关键词： 2,3-丁二醇 , 立体构型 , 合成机理 , 全细胞催化 , 合成生物学

Biotechnological production of 2,3-butanediol stereoisomers: synthetic mechanism and realized methods

SHEN Mengqiu ^1, , JI Xiaojun ^2, , NIE Zhikui ^3, , XIA Zhifang ^4, , YANG Han ^5, , HUANG He ^6,

1.南京工业大学生物与制药工程学院,江苏南京211816

2.南京工业大学生物与制药工程学院,江苏南京211816

3.南京工业大学生物与制药工程学院,江苏南京211816

4.南京工业大学生物与制药工程学院,江苏南京211816

5.南京工业大学生物与制药工程学院,江苏南京211816

6.南京工业大学生物与制药工程学院,江苏南京211816;南京工业大学材料化学工程国家重点实验室,江苏南京210009

Keywords： 2,3-butanediol , stereoisomer , synthetic mechanism , whole cell catalysis , synthetic biology

总结了不同2,3-丁二醇立体异构体的生物合成机制,以及有利于这些立体异构体高效合成的一些策略,包括构建全细胞催化剂及利用合成生物学技术重建代谢途径等先进方法；同时指出,未来的研究重点是进一步利用合成生物学的方法,以提高不同立体构型2,3-丁二醇的生物合成能力,并建立这些异构体高效可行的分离方法.

参考文献

[1]	Ragauskas AJ;Williams CK;Davison BH;Britovsek G;Cairney J;Eckert CA;Frederick WJ;Hallett JP;Leak DJ;Liotta CL .The path forward for biofuels and biomaterials[J].Science,2006(5760):484-489.
[2]	Ji X J;Huang H;Nie Z K;Qu L Xu Q Tsao G T .[J].Advances in Biochemical Engineering/Biotechnology,2012,128:199.
[3]	Garg S;Jain A .[J].Bioresource Technology,1995,51:103.
[4]	van Haveren J;Scott E L;Sanders J .[J].Biofuels Bioprod Bioref,2007,2:41.
[5]	Syu MJ. .Biological production of 2,3-butanediol [Review][J].Applied Microbiology and Biotechnology,2001(1):10-18.
[6]	Liu R.;Hogberg HE. .Chemoenzymatic preparation of (2S,3S)- and (2R,3R)-2,3-butanediols and their esters from mixtures of d,l- and meso-diols[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2001(5):771-778.
[7]	罗云富,李援朝.手性邻二醇--（2 S,3R）-1,2,3-丁三醇-1-对甲苯磺酸酯的不对称合成[J].有机化学,2002(04):262-264.
[8]	Ceskis B;Lebedavia K V;Moiseankov A M.[J].Izv Akad Nauk SSSR Ser Khim,1988(04):865.
[9]	Shigeki I;Takehiro T;Hiroyuki I .[J].Jpn Kokai Tokkyo Koho,1992,91:623.
[10]	Yan Y;Lee C C;Liao J C .[J].Organic and Biological Chemistry,2009,7:3914.
[11]	Hasanuzzaman M;Yoshimura M .Effects of straight chain alcohols on specific isoforms of adenylyl cyclase.[J].Alcoholism: Clinical and experimental research,2010(4):743-749.
[12]	纪晓俊,聂志奎,黎志勇,高振,黄和.生物制造2,3-丁二醇：回顾与展望[J].化学进展,2010(12):2450-2461.
[13]	Ji X J;Huang H;Zhu J G;Ren L J Nie Z K Du J Li S .[J].Appl Microbiol Bioteehnol,2010,85:1751.
[14]	Ji, X.-J.;Nie, Z.-K.;Huang, H.;Ren, L.-J.;Peng, C.;Ouyang, P.-K. .Elimination of carbon catabolite repression in Klebsiella oxytoca for efficient 2,3-butanediol production from glucose-xylose mixtures[J].Applied Microbiology and Biotechnology,2011(4):1119-1125.
[15]	Ji XJ;Huang H;Li S;Du J;Lian M .Enhanced 2,3-butanediol production by altering the mixed acid fermentation pathway in Klebsiella oxytoca[J].Biotechnology Letters,2008(4):731-734.
[16]	Ji, XJ;Huang, H;Du, J;Zhu, JG;Ren, LJ;Li, S;Nie, ZK .Development of an industrial medium for economical 2,3-butanediol production through co-fermentation of glucose and xylose by Klebsiella oxytoca[J].Bioresource Technology: Biomass, Bioenergy, Biowastes, Conversion Technologies, Biotransformations, Production Technologies,2009(21):5214-5218.
[17]	Ji X J;Huang H;Du J;Zhu J G Ren L J Hu N Li S .[J].Bioresource Technology,2009,100:3410.
[18]	Nie, Z.-K.;Ji, X.-J.;Huang, H.;Du, J.;Li, Z.-Y.;Qu, L.;Zhang, Q.;Ouyang, P.-K. .An effective and simplified fed-batch strategy for improved 2,3-butanediol production by Klebsiella oxytoca[J].Applied biochemistry and biotechnology, Part A. enzyme engineering and biotechnology,2011(8):946-953.
[19]	Ji X J;Huang H;Ouyang P K .[J].Biotechnology Advances,2011,29:351.
[20]	Maddox I S .[J].Bio-Technology,1996,6:269.
[21]	Celinska, E;Grajek, W .Biotechnological production of 2,3-butanediol-Current state and prospects[J].Biotechnology Advances,2009(6):715-725.
[22]	Voloch M;Ladisch M R;Rodwell V W;Tsao G T .[J].Biotechnology and Bioengineering,1983,25:173.
[23]	Ui S;Masuda H;Muraki H .[J].Agricultural and Biological Chemistry,1984,48:2837.
[24]	Juni E;Heym G A .[J].Journal of Bacteriology,1956,72:452.
[25]	Lopez J;Fortnagel P .[J].Biochimica et Biophysica Acta,1972,279:554.
[26]	Taylor M B;Juni E .[J].Biophys Acta,1960,39:448.
[27]	H(o)hn-Bentz H;Redler E .[J].Archives of Microbiology,1978,116:197.
[28]	Ui S;Masuda H;Muraki H .[J].Agricultural and Biological Chemistry,1984,48:2835.
[29]	Ui S;Matsuyama N;Masuda H;Muraki H .[J].JOURNAL OF FERMENTATION TECHNOLOGY,1984,62:551.
[30]	Ui S;Masuda T;Masuda H;Muraki H .[J].JOURNAL OF FERMENTATION TECHNOLOGY,1986,64:481.
[31]	Ui S;Hosaka T;Watanabe K;Mimura A .[J].Journal of Fermentation and Bioengineering,1998,85:79.
[32]	González E;Femández M R;Larroy C;Solà L Pericàs M A Parés X Biosca J A .[J].Journal of Biological Chemistry,2000,275:35876.
[33]	Nicholson WL .The Bacillus subtilis ydjL (bdhA) Gene Encodes Acetoin Reductase/2,3-Butanediol Dehydrogenase[J].Applied and Environmental Microbiology,2008(22):6832-6838.
[34]	Otagiri M;Ui S;Takusagawa .Structural basis for chiral substrate recognition by two 2,3-butanediol dehydrogenases.[J].FEBS Letters: For the Rapid Publication of Short Reports in Biochemistry, Biophysics and Molecular Biology,2010(1):219-223.
[35]	Yu, B.;Sun, J.;Bommareddy, R.R.;Song, L.;Zeng, A.-P. .Novel (2R,3R)-2,3-butanediol dehydrogenase from potential industrial strain Paenibacillus polymyxa ATCC 12321[J].Applied and Environmental Microbiology,2011(12):4230-4233.
[36]	Takeda M;Muranushi T;Inagaki S;Nakao T Motomatsu S Suzuki I Koizumi J .[J].Bioscience Biotechnology and Biochemistry,2011,75:2384.
[37]	梅建凤,闵航,吕镇梅.利用酵母细胞生物催化合成2-苯乙醇[J].催化学报,2007(11):993-998.
[38]	王净,田晶,许建和.睾丸酮丛毛单胞菌生物催化合成对苯二甲酸[J].催化学报,2006(04):297-298.
[39]	刘春巧,张淑荣,张鹏.黄单胞菌生物催化合成α-熊果苷[J].催化学报,2006(04):361-364.
[40]	王丹,张强,李旺,戚南昌,郭春晓,杨志荣,张杰.酵母静息细胞催化丙酮酸乙酯不对称还原制（S）-乳酸乙酯[J].催化学报,2011(06):1035-1039.
[41]	敬科举,徐志南,林建平,岑沛霖.重组大肠杆菌细胞不对称还原4-氯乙酰乙酸乙酯合成（R）-（+）-4-氯-3-羟基丁酸乙酯[J].催化学报,2005(11):993-998.
[42]	Yamada-Onodera K;Yamamoto H;Kawahara N;Tani Y .Expression of the gene of glycerol dehydrogenase from Hansenula polymorpha Dl-1 in Escherichia coli for the production of chiral compounds[J].Acta Biotechnologica,2002(3/4):355-362.
[43]	Xiao Z J;Lü C J;Gao C;Qin J Y Ma C Q Liu Z Liu P H Li L X Xu P .[J].PLoS One,2010,5:e8860.
[44]	Liu, Z.;Qin, J.;Gao, C.;Hua, D.;Ma, C.;Li, L.;Wang, Y.;Xu, P. .Production of (2S,3S)-2,3-butanediol and (3S)-acetoin from glucose using resting cells of Klebsiella pneumonia and Bacillus subtilis[J].Bioresource Technology: Biomass, Bioenergy, Biowastes, Conversion Technologies, Biotransformations, Production Technologies,2011(22):10741-10744.
[45]	Ui S;Takusagawa Y;Ohtsuki T;Mimura A;Ohkuma M;Kudo T .Stereochemical applications of the expression of the L-2,3-butanedioldehydrogenase gene in Escherichia coli[J].Letters in Applied Microbiology,2001(2):93-98.
[46]	Ui S;Takusagawa Y;Sato T;Ohtsuki T Mimura A Ohkuma M Kudo T .[J].Letters in Applied Microbiology,2004,39:533.
[47]	Li, L.;Wang, Y.;Zhang, L.;Ma, C.;Wang, A.;Tao, F.;Xu, P..Biocatalytic production of (2S,3S)-2,3-butanediol from diacetyl using whole cells of engineered Escherichia coli[J].Bioresource Technology: Biomass, Bioenergy, Biowastes, Conversion Technologies, Biotransformations, Production Technologies,2012:111-116.
[48]	Ui S;Okajima Y;Mimura A;Kanai H Kudo T .[J].JFerment Bioeng,1997,84:185.
[49]	Nielsen D R;Yoon S H;Yuan C J;Prather K L J .[J].Journal of Biotechnology,2010,5:274.
[50]	Li, Z.-J.;Jian, J.;Wei, X.-X.;Shen, X.-W.;Chen, G.-Q. .Microbial production of meso-2,3-butanediol by metabolically engineered Escherichia coli under low oxygen condition[J].Applied Microbiology and Biotechnology,2010(6):2001-2009.
[51]	Siemerink, M.A.J.;Kuit, W.;Contreras, A.M.L.;Eggink, G.;van der Oost, J.;Kengen, S.W.M. .D-2,3-butanediol production due to heterologous expression of an acetoin reductase in Clostridium acetobutylicum[J].Applied and Environmental Microbiology,2011(8):2582-2588.
[52]	Lee S;Kim B;Park K;Um Y Lee J .[J].Applied Biochemistry and Biotechnology,2012,166:1811.
[53]	Wang, Q.;Chen, T.;Zhao, X.;Chamu, J. .Metabolic engineering of thermophilic Bacillus licheniformis for chiral pure D-2,3-butanediol production[J].Biotechnology and Bioengineering,2012(7):1610-1621.
[54]	Shin, H.-D.;Yoon, S.-H.;Wu, J.;Rutter, C.;Kim, S.-W.;Chen, R.R..High-yield production of meso-2,3-butanediol from cellodextrin by engineered E. coli biocatalysts[J].Bioresource Technology: Biomass, Bioenergy, Biowastes, Conversion Technologies, Biotransformations, Production Technologies,2012:367-373.

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