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D-阿洛酮糖及其合成研究进展

  • 贾东旭 ,
  • 孙晨奕 ,
  • 彭晨 ,
  • 柳志强 ,
  • 李勉 ,
  • 王红艳 ,
  • 陈凯茜 ,
  • 程新平 ,
  • 陈德水
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  • 1(浙江工业大学 浙江省生物有机合成技术研究重点实验室,浙江 杭州,310014)
    2(浙江华康药业股份有限公司,浙江 开化,324032)
博士,副教授(柳志强教授为通讯作者,E-mail:microliu@zjut.edu.cn)

收稿日期: 2020-08-01

  修回日期: 2020-09-10

  网络出版日期: 2021-03-08

基金资助

衢州市科技计划项目(2019K09)

Advances on D-psicose and its synthesis

  • JIA Dongxu ,
  • SUN Chenyi ,
  • PENG Chen ,
  • LIU Zhiqiang ,
  • LI Mian ,
  • WANG Hongyan ,
  • CHEN Kaixi ,
  • CHENG Xinping ,
  • CHEN Deshui
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  • 1(Key Laboratory of Bioorganic Synthesis of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, China)
    2(Zhejiang Huakang Pharmaceutical Co., Ltd., Kaihua 324032, China)

Received date: 2020-08-01

  Revised date: 2020-09-10

  Online published: 2021-03-08

摘要

D-阿洛酮糖是一种具有保健功能的己酮糖,可以预防糖尿病、维持正常血脂水平,避免传统甜味剂对人体造成的代谢负担,具有重要的应用价值,但在自然界中含量稀少,近年来涌现多种D-阿洛酮糖的合成方法。文章围绕D-阿洛酮糖的功能、化学合成法和生物酶异构化法等内容开展综述,重点阐述了D-阿洛酮糖3-差向异构酶的来源及性质、结构及催化机制、分子改造、多酶偶联、食品级表达等方面的研究进展,旨在推进生物转化制备D-阿洛酮糖的工业发展,为保障公众营养健康提供新思路。

本文引用格式

贾东旭 , 孙晨奕 , 彭晨 , 柳志强 , 李勉 , 王红艳 , 陈凯茜 , 程新平 , 陈德水 . D-阿洛酮糖及其合成研究进展[J]. 食品与发酵工业, 2021 , 47(3) : 211 -217 . DOI: 10.13995/j.cnki.11-1802/ts.025236

Abstract

D-psicose is a kind of hexoketose with specific health care function, which is usually applied to prevent diabetes, maintain normal blood lipid level and avoid the negative effect of traditional sweeteners on human body. Thus, it shows important application value. In recent years, a variety of methods regarding synthesis of D-psicose have emerged with the aim to solve the problem of its rare content in nature. In this paper, the aspects including physiological function, chemical synthesis and enzymatic isomerization process of D-psicose were reviewed. Among them, enzymatic resources and properties, crystal structure and corresponding catalytic mechanism, molecular modification, multi enzyme co-expression, expression in food grade hosts are systematically elucidated. This review may shed light on improving the industrial preparation level of D-psicose via biotransformation method and provide new ideas for maintaining public nutrition and health care.

参考文献

[1] GRANSTRÖM T B,TAKATA G,TOKUDA M,et al.Izumoring:A novel and complete strategy for bioproduction of rare sugars[J].Journal of Bioscience and Bioengineering,2004,97(2):89-94.
[2] CHATTOPADHYAY S,RAYCHAUDHURI U,CHAKRABORTY R.Artificial sweeteners-A review[J].Journal of Food Science and Technology,2014,51(4):611-621.
[3] KIMURA T,KANASAKI A,HAYASHI N,et al.D-allulose enhances postprandial fat oxidation in healthy humans[J].Nutrition,2017,43-44:16-20.
[4] IWASAKI Y,SENDO M,DEZAKI K,et al.GLP-1 release and vagal afferent activation mediate the beneficial metabolic and chronotherapeutic effects of D-allulose[J].Nature Communications,2018,9:113.
[5] SUNA S,YAMAGUCHI F,KIMURA S,et al.Preventive effect of D-psicose,one of rare ketohexoses,on di-(2-ethylhexyl) phthalate (DEHP)-induced testicular injury in rat[J].Toxicology Letters,2007,173(2):107-117.
[6] TAKATA M K,YAMAGUCHI F,NAKANOSE K,et al.Neuroprotective effect of D-psicose on 6-hydroxydopamine-induced apoptosis in rat pheochromocytoma (PC12) cells[J].Journal of Bioscience and Bioengineering,2005,100(5):511-516.
[7] ANDREANA P R,MCLELLAN J S,CHEN Y,et al.Synthesis of 2,6-dideoxysugars via ring-closing olefinic metathesis[J].Organic Letters,2002,4(22):3 875-3 878.
[8] NORTHRUP A B,MACMILLAN D W C.Two-step synthesis of carbohydrates by selective aldol reactions[J].Cheminform,2004,5691:1 752-1 754.
[9] DONER L W.Isomerization of D-fructose by base:Liquid-chromatographic evaluation and the isolation of D-psicose[J].Carbohydrate Research,1979,70(2):209-216.
[10] SOENGAS R,IZUMORI K,SIMONE M I,et al.Kiliani reactions on ketoses:Branched carbohydrate building blocks from D-tagatose and D-psicose[J].Tetrahedron Letters,2005,46(34):5 755-5 759.
[11] 方志杰, 李松,程杰,等.一种由糖酸内酯出发合成稀有己酮糖和庚酮糖的方法:中国,200910031931.7[P].2009-07-03.
FANG Z J,LI S,CHENG J,et al.A method for the synthesis of rare hexoses and heptanoses from glycoacid lactones:China,200910031931.7[P].2009-07-03.
[12] IZUMORI K,KHAN A R,OKAYA H,et al.A new enzyme,D-ketohexose 3-Epimerase,from Pseudomonas sp.ST-24[J].Bioscience Biotechnology and Biochemistry,1993,57(6):1 037-1 039.
[13] KIM H J,HYUN E K,KIM Y S,et al.Characterization of an Agrobacterium tumefaciens D-psicose 3-Epimerase that converts D-fructose to D-psicose[J].Applied and Environmental Microbiology,2006,72(2):981-985.
[14] ZHU Y M,MEN Y,BAI W,et al.Overexpression of D-psicose 3-epimerase from Ruminococcus sp.in Escherichia coli and its potential application in D-psicose production[J].Biotechnology Letters,2012,34(10):1 901-1 906.
[15] JIA M,MU W M,CHU F F,et al.A D-psicose 3-epimerase with neutral pH optimum from Clostridium bolteae for D-psicose production:Cloning,expression,purification,and characterization[J].Applied Microbiology and Biotechnology,2014,98(2):717-725.
[16] YOSHIHARA A,KOZAKAI T,SHINTANI T,et al.Purification and characterization of D-allulose 3-epimerase derived from Arthrobacter globiformis M30,a GRAS microorganism[J].Journal of Bioscience and Bioengineering,2017,123(2):170-176.
[17] ZHANG W L,LI H,ZHANG T,et al.Characterization of a D-psicose 3-epimerase from Dorea sp.CAG317 with an acidic pH optimum and a high specific activity[J].Journal of Molecular Catalysis B:Enzymatic,2015,120:68-74.
[18] ZHANG W L,ZHANG T,JIANG B,et al.Biochemical characterization of a D-psicose 3-epimerase from Treponema primitia ZAS-1 and its application on enzymatic production of D-psicose[J].Journal of the Science of Food and Agriculture,2016,96(1):49-56.
[19] MU W M,CHU F F,XING Q C,et al.Cloning,expression,and characterization of a D-psicose 3-Epimerase from Clostridium cellulolyticum H10[J].Journal of Agricultural and Food Chemistry,2011,59(14):7 785-7 792.
[20] ZHANG W L,FANG D,ZHANG T,et al.Characterization of a metal-dependent D-psicose 3-epimerase from a novel strain,Desmospora sp.8437[J].Journal of Agricultural and Food Chemistry,2013,61(47):11 468-11 476.
[21] MU W M,ZHANG W L,FANG D,et al.Characterization of a D-psicose-producing enzyme,D-psicose 3-epimerase,from Clostridium sp.[J].Biotechnology Letters,2013,35(9):1 481-1 486.
[22] ZHANG W L,FANG D,XING Q C,et al.Characterization of a novel metal-dependent D-psicose 3-epimerase from Clostridium scindens 35704[J].PLoS ONE,2013,8(4):e62 987.
[23] PARK C,KIM T,HONG S,et al.D-allulose production from D-fructose by permeabilized recombinant cells of Corynebacterium glutamicum cells expressing D-allulose 3-epimerase Flavonifractor plautii[J].PLoS One,2016,11(7):e160 044.
[24] KIM K,KIM H,OH D,et al.Crystal structure of D-psicose 3-epimerase from Agrobacterium tumefaciens and its complex with true substrate D-fructose:A pivotal role of metal in catalysis,an active site for the non-phosphorylated substrate,and its conformational changes[J].Journal of Molecular Biology,2006,361(5):920-931.
[25] QI Z L,ZHU Z L,WANG J W,et al.Biochemical analysis and the preliminary crystallographic characterization of D-tagatose 3-epimerase from Rhodobacter sphaeroides[J].Microbial Cell Factories,2017,16(1):193.
[26] KIM H,LIM B,YEOM S,et al.Roles of Ile66 and Ala107 of D-psicose 3-epimerase from Agrobacterium tumefaciens in binding O6 of its substrate,D-fructose[J].Biotechnology Letters,2010,32(1):113-118.
[27] 张黎丽,朱玥明,门燕,等.来源于瘤胃菌Ruminococcus sp.的D-阿洛酮糖3-差向异构酶的底物结合位点分析[J].微生物学通报,2014,41(5):811-817.
ZHANG L L,ZHU Y M,MEN Y,et al.Substrate-binding site of D-psicose 3-epimerase from Ruminococcus sp.[J].Microbiology China,2014,41(5):811-817.
[28] ZHU Z L,GAO D K,LI C,et al.Redesign of a novel D-allulose 3-epimerase from Staphylococcus aureus for thermostability and efficient biocatalytic production of D-allulose[J].Microbial Cell Factories,2019,18(1):59.
[29] ZHU J X,LI Y,WANG J Z,et al.Adaptive steered molecular dynamics combined with protein structure networks revealing the mechanism of Y68I/G109P mutations that enhance the catalytic activity of D-psicose 3-epimerase from Clostridium bolteae[J].Frontiers in Chemistry,2018,6:437.
[30] TOLMAN R C.The temperature coefficient of photochemical reaction rate[J].Journal of the American Chemical Society,1923,45(10):2 285-2 296.
[31] CHOI J,JU Y,YEOM S,et al.Improvement in the thermostability of D-psicose 3-epimerase from Agrobacterium tumefaciens by random and site-directed mutagenesis[J].Applied and Environmental Microbiology,2011,77(20):7 316-7 320.
[32] ZHANG W L,JIA M,YU S H,et al.Improving the thermostability and catalytic efficiency of the d-psicose 3-epimerase from Clostridium bolteae ATCC BAA-613 using site-directed mutagenesis[J].Journal of Agricultural and Food Chemistry,2016,64(17):3 386-3 393.
[33] ZHANG W L,ZHANG Y M,HUANG J W,et al.Thermostability improvement of the D-allulose 3-epimerase from Dorea sp.CAG317 by site-directed mutagenesis at the interface regions[J].Journal of Agricultural and Food Chemistry,2018,66(22):5 593-5 601.
[34] MAO S H,CHENG X T,ZHU Z L,et al.Engineering a thermostable version of D-allulose 3-epimerase from Rhodopirellula baltica via site-directed mutagenesis based on B-factors analysis[J].Enzyme and Microbial Technology,2020,132:109 441.
[35] 谢雪原, 周华,高震,等.多酶偶联反应体系的研究和应用[J].化工进展,2004,23(8):864-868.
XIE X Y,ZHOU H,GAO Z,et al.Study and application of coupled multienzyme reaction system[J].Chemical Industry and Engineering Progress,2004,23(8):864-868.
[36] MEN Y,ZHU Y M,ZENG Y,et al.Co-expression of D-glucose isomerase and D-psicose 3-epimerase:Development of an efficient one-step production of D-psicose[J].Enzyme and Microbial Technology,2014,64-65:1-5.
[37] 高雅慧, 金则成,钱超,等.基于RhaD醛缩酶的“一锅四酶法”合成D-山梨糖和D-阿洛酮糖[J].食品工业科技,2013,34(21):210-214.
GAO Y H,JIN Z C,QIAN C,et al.One pot four enzyme synthesis of D-sorbose and D-psicose based on aldolase RhaD[J].Science and Technology of Food Industry,2013,34(21):210-214.
[38] 韩文佳, 朱玥明,柏玮,等.双酶偶联转化果糖制备含有稀少糖的混合糖液[J].生物工程学报,2014,30(1):90-97.
HAN W J,ZHU Y M,BO W et al.Production of sugar syrup containing rare sugar using dual-enzyme coupled reaction system[J].Chinese Journal of Biotechnology,2014,30(1):90-97.
[39] 贾敏, 沐万孟,张涛,等.D-阿洛酮糖3-差向异构酶基因在枯草芽孢杆菌中的表达[J].食品与生物技术学报,2014,33(11):1 129-1 135.
JIA M,MU W M,ZHANG T,et al.Expression of D-psicose 3-epimerase in Bacillus subtilis[J].Journal of Food Science and Biotechnology,2014,33(11):1 129-1 135.
[40] HE W W,JIANG B,MU W M,et al.Production of D-allulose with D-psicose 3-epimerase expressed and displayed on the surface of Bacillus subtilis spores[J].Journal of Agricultural and Food Chemistry,2016,64(38):7 201-7207
[41] CHEN J Q,ZHAO L Q,FU G,et al.A novel strategy for protein production using non-classical secretion pathway in Bacillus subtilis[J].Microbial Cell Factories,2016,15(1):1-16.
[42] YANG J G,TIAN C Y,ZHANG T,et al.Development of food-grade expression system for D-allulose 3-epimerase preparation with tandem isoenzyme genes in Corynebacterium glutamicum and its application in conversion of cane molasses to D-allulose[J].Biotechnology and Bioengineering,2019,116(4):745-756.
[43] LIM B,KIM H,OH D.A stable immobilized D-psicose 3-epimerase for the production of D-psicose in the presence of borate[J].Process Biochemistry,2009,44(8):822-828.
[44] YOSHIHARA A,KOZAKAI T,SHINTANI T,et al.Purification and characterization of D-allulose 3-epimerase derived from Arthrobacter globiformis M30,a GRAS microorganism[J].Journal of Bioscience and Bioengineering,2017,123(2):170-176.
[45] TSENG C,LIAO C,SUN Y,et al.Immobilization of Clostridium cellulolyticum D-psicose 3-epimerase on artificial oil bodies[J].Journal of Agricultural and Food Chemistry,2014,62(28):6 771-6 776.
[46] LI C,LIN J Q,GUO Q Q,et al.D-psicose 3-epimerase secretory overexpression,immobilization,and D-psicose biotransformation,separation and crystallization[J].Journal of Chemical Technology & Biotechnology,2018,93(2):350-357.
[47] 孙帆, 宿玲恰,张康,等.D-阿洛酮糖3-差向异构酶在枯草芽孢杆菌中的高效表达及固定化细胞研究[J].中国生物工程杂志,2018,38(7):83-88.
SUN F,SU L Q,ZHANG K,et al.D-psicose 3-epimerase gene overexpression in Bacillus subtilis and immobilization of cells[J].China Biotechnology,2018,38(7):83-88.
[48] NARAYAN PATEL S,SINGH V,SHARMA M,et al.Development of a thermo-stable and recyclable magnetic nanobiocatalyst for bioprocessing of fruit processing residues and D-allulose synthesis[J].Bioresource Technology,2018,247:633-639.
[49] ZHANG X J,FAN H H,LIU N,et al.A novel self-sufficient biocatalyst based on transaminase and pyridoxal 5′-phosphate covalent co-immobilization and its application in continuous biosynthesis of sitagliptin[J].Enzyme and Microbial Technology,2019,130:109 362.
[50] 金利群, 郭东京,廖承军.固定化葡萄糖异构酶的研究进展[J].发酵科技通讯,2015,44(3):47-51.
JIN L Q,GUO D J,LIAO C J.Progress in immobilized glucose isomerase[J].Bulletin of Fermentation Science and Technology,2015,44(3):47-51.
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