Abstract
Acetoin is an important four-carbon compound that has many applications in foods, chemical synthesis, cosmetics, cigarettes, soaps, and detergents. Its stereoisomer (S)-acetoin, a high-value chiral compound, can also be used to synthesize optically active drugs, which could enhance targeting properties and reduce side effects. Recently, considerable progress has been made in the development of biotechnological routes for (S)-acetoin production. In this review, various strategies for biological (S)- acetoin production are summarized, and their constraints and possible solutions are described. Furthermore, future prospects of biological production of (S)-acetoin are discussed.
Keywords: (S)-Acetoin, Chiral compound, Whole-cell biocatalyst, In situ cofactor regeneration, Biological production, Side effects.
Graphical Abstract
[http://dx.doi.org/10.2172/926125]
[http://dx.doi.org/10.1016/j.biotechadv.2014.01.002] [PMID: 24412764]
[http://dx.doi.org/10.1016/j.lungcan.2009.03.029] [PMID: 19409642]
[http://dx.doi.org/10.1002/cam4.162] [PMID: 24402867]
[http://dx.doi.org/10.1016/j.biotechadv.2011.01.007] [PMID: 21272631]
[http://dx.doi.org/10.1080/07388551.2017.1299680] [PMID: 28423947]
[http://dx.doi.org/10.1016/j.bmc.2003.10.017] [PMID: 14723968]
[http://dx.doi.org/10.1016/S0960-894X(02)01058-2] [PMID: 12643944]
[http://dx.doi.org/10.1016/S0957-4166(00)00349-9]
[PMID: 23701367]
[http://dx.doi.org/10.18632/oncotarget.7815] [PMID: 26942877]
[http://dx.doi.org/10.1016/j.ygeno.2015.12.005] [PMID: 26724497]
[http://dx.doi.org/10.18632/oncotarget.13758] [PMID: 27926534]
[http://dx.doi.org/10.1016/j.omtn.2018.03.012] [PMID: 29858081]
[http://dx.doi.org/10.1093/nar/gks1450] [PMID: 23303794]
[http://dx.doi.org/10.1155/2014/623149] [PMID: 24967386]
[PMID: 28427142]
[http://dx.doi.org/10.1155/2014/286419] [PMID: 24991545]
[http://dx.doi.org/10.1016/j.ygeno.2018.1001.1005] [PMID: 29360500]
[http://dx.doi.org/10.1016/j.ab.2013.05.024] [PMID: 23756733]
[http://dx.doi.org/10.1093/nar/gku1019] [PMID: 25361964]
[http://dx.doi.org/10.1093/bioinformatics/bty508] [PMID: 29931187]
[http://dx.doi.org/10.1016/j.ab.2015.08.021] [PMID: 26314792]
[http://dx.doi.org/10.7150/ijbs.24616] [PMID: 29989083]
[http://dx.doi.org/10.18632/oncotarget.11975] [PMID: 27626500]
[http://dx.doi.org/10.1016/j.jtbi.2010.12.024] [PMID: 21168420]
[http://dx.doi.org/10.1038/nature06531] [PMID: 18235503]
[http://dx.doi.org/10.1038/nsmb.1707] [PMID: 19898475]
[http://dx.doi.org/10.1038/nsb1101-990] [PMID: 11685248]
[http://dx.doi.org/10.1038/ni.1943] [PMID: 20890284]
[http://dx.doi.org/10.1038/nature10257] [PMID: 21785437]
[http://dx.doi.org/10.1038/nature12283] [PMID: 23739335]
[http://dx.doi.org/10.1038/nature17656] [PMID: 27135929]
[http://dx.doi.org/10.2174/138920305774329377] [PMID: 16248792]
[http://dx.doi.org/10.1110/ps.051528905] [PMID: 16131665]
[http://dx.doi.org/10.1093/glycob/cwi016] [PMID: 15563715]
[http://dx.doi.org/10.2174/0929866521666141019192221] [PMID: 25329332]
[http://dx.doi.org/10.2174/0929866511107010966] [PMID: 21592084]
[http://dx.doi.org/10.1021/bi101435c] [PMID: 21189021]
[http://dx.doi.org/10.1074/jbc.M804916200] [PMID: 18782776]
[http://dx.doi.org/10.2174/1568026615666150819104617] [PMID: 26286215]
[http://dx.doi.org/10.1016/S0014-5793(00)01333-8] [PMID: 10745077]
[http://dx.doi.org/10.1016/S0014-5793(97)01246-5] [PMID: 9426218]
[http://dx.doi.org/10.1021/pr049931q] [PMID: 15359741]
[http://dx.doi.org/10.1021/pr049905s] [PMID: 15473697]
[http://dx.doi.org/10.1021/pr050135+] [PMID: 16212418]
[http://dx.doi.org/10.1016/j.bbrc.2004.05.016] [PMID: 15178425]
[http://dx.doi.org/10.1016/j.bbrc.2006.12.235] [PMID: 17266937]
[http://dx.doi.org/10.2174/0929867043364667] [PMID: 15279552]
[http://dx.doi.org/10.1021/bi00077a008] [PMID: 7687145]
[PMID: 7686907]
[http://dx.doi.org/10.1007/BF01992044] [PMID: 7507441]
[http://dx.doi.org/10.1042/bj1870829] [PMID: 7188428]
[http://dx.doi.org/10.1042/bj2220169] [PMID: 6477507]
[http://dx.doi.org/10.1006/abio.1994.1405] [PMID: 7529005]
[http://dx.doi.org/10.2174/15680266113139990003] [PMID: 23647538]
[http://dx.doi.org/10.1016/j.jtbi.2011.06.006] [PMID: 21718705]
[http://dx.doi.org/doi.org/10.1182/blood.V104.11.3539.3539]
[http://dx.doi.org/10.2174/1568026617666170414150730] [PMID: 28413949]
[http://dx.doi.org/10.1371/journal.pone.0055844] [PMID: 23409062]
[http://dx.doi.org/10.1016/j.ab.2015.12.009] [PMID: 26723495]
[http://dx.doi.org/10.1016/j.jtbi.2016.01.020] [PMID: 26807806]
[http://dx.doi.org/10.18632/oncotarget.10027] [PMID: 27322424]
[http://dx.doi.org/10.18632/oncotarget.9148] [PMID: 27153555]
[http://dx.doi.org/10.1371/journal.pone.0105018] [PMID: 25121969]
[http://dx.doi.org/10.7717/peerj.171] [PMID: 24109555]
[http://dx.doi.org/10.4236/ns.2011.310111]
[http://dx.doi.org/10.18632/oncotarget.17104] [PMID: 28476023]
[http://dx.doi.org/10.1016/j.ab.2015.12.017] [PMID: 26748145]
[http://dx.doi.org/10.1016/j.ab.2014.12.009] [PMID: 25596338]
[http://dx.doi.org/10.1016/j.dib.2015.04.021] [PMID: 26217768]
[http://dx.doi.org/10.1002/prot.1035] [PMID: 11288174]
[http://dx.doi.org/10.2174/157016409789973707]
[http://dx.doi.org/10.1016/j.ab.2014.04.001] [PMID: 24732113]
[http://dx.doi.org/10.1039/C5MB00155B] [PMID: 26099739]
[http://dx.doi.org/10.1093/nar/gkv458] [PMID: 25958395]
[http://dx.doi.org/10.4236/ns.2017.94007]
[http://dx.doi.org/10.2174/1568026617666170414145508] [PMID: 28413951]
[http://dx.doi.org/10.1021/pr025527k] [PMID: 12645914]
[http://dx.doi.org/10.1039/C7MB00267J] [PMID: 28702580]
[http://dx.doi.org/10.1016/j.gene.2017.07.036] [PMID: 28728979]
[http://dx.doi.org/10.1093/bioinformatics/btx476] [PMID: 29036535]
[http://dx.doi.org/10.1093/bioinformatics/btx711] [PMID: 29106451]
[PMID: 28989035]
[http://dx.doi.org/10.4236/ns.2017.99032]
[http://dx.doi.org/10.1016/j.ygeno.2017.08.005] [PMID: 28818512]
[http://dx.doi.org/10.1039/c3mb25555g] [PMID: 23536215]
[http://dx.doi.org/10.1002/bip.360340114] [PMID: 8110966]
[http://dx.doi.org/10.1016/j.jbiotec.2014.07.441] [PMID: 25450636]
[http://dx.doi.org/10.1016/j.ymben.2014.11.010] [PMID: 25499652]
[http://dx.doi.org/10.1016/S1389-1723(99)80013-9] [PMID: 16232430]
[http://dx.doi.org/10.1080/10408410701364604] [PMID: 17558661]
[http://dx.doi.org/10.1016/j.pep.2012.02.006] [PMID: 22387083]
[http://dx.doi.org/10.1016/0385-6380(86)90070-1]
[http://dx.doi.org/10.1007/s00253-014-5526-9] [PMID: 24535253]
[http://dx.doi.org/10.1016/j.biortech.2011.08.110] [PMID: 21945208]
[http://dx.doi.org/10.1016/0922-338X(96)85137-3]
[http://dx.doi.org/10.1002/jctb.5702]
[http://dx.doi.org/10.2174/1568026617666170504101646] [PMID: 28474550]
[http://dx.doi.org/10.3389/fmicb.2015.00150] [PMID: 25762991]
[http://dx.doi.org/10.1016/j.ijfoodmicro.2014.01.017] [PMID: 24531037]
[http://dx.doi.org/10.1128/AEM.01711-14] [PMID: 25063653]
[http://dx.doi.org/10.1002/cctc.201300904]
[http://dx.doi.org/10.1039/p19830002435]
[http://dx.doi.org/10.1016/j.biotechadv.2014.04.001] [PMID: 24751381]
[http://dx.doi.org/10.1002/jctb.3791]
[http://dx.doi.org/10.1016/j.biortech.2012.05.108] [PMID: 22728188]
[PMID: 16348274]
[http://dx.doi.org/10.1002/bit.26038] [PMID: 27344975]
[http://dx.doi.org/10.1080/09168451.2014.943649] [PMID: 25082080]
[http://dx.doi.org/10.1007/s10295-014-1483-7] [PMID: 25037723]
[http://dx.doi.org/10.1007/s00253-013-4870-5] [PMID: 23568047]
[http://dx.doi.org/10.1016/j.biortech.2013.02.115] [PMID: 23587814]
[http://dx.doi.org/10.1038/srep02643] [PMID: 24025762]
[http://dx.doi.org/10.1007/b98911] [PMID: 15791939]
[http://dx.doi.org/10.1007/s10295-008-0345-6] [PMID: 18392870]
[http://dx.doi.org/10.1371/journal.pone.0008860] [PMID: 20126645]
[http://dx.doi.org/10.3390/molecules23030691] [PMID: 29562693]
[http://dx.doi.org/10.5936/csbj.201210002] [PMID: 24688662]
[http://dx.doi.org/10.1007/s00449-004-0373-1] [PMID: 15309606]
[http://dx.doi.org/10.1128/ecosalplus.ESP-0010-2015] [PMID: 27223822]
[PMID: 25577396]
[http://dx.doi.org/10.1007/s00253-007-1005-x] [PMID: 17486338]
[http://dx.doi.org/10.1016/j.ymben.2016.11.012] [PMID: 27931827]
[http://dx.doi.org/10.1371/journal.pone.0107143] [PMID: 25192451]
[http://dx.doi.org/10.1186/s13068-016-0502-5] [PMID: 27099629]
[http://dx.doi.org/10.1186/s13068-016-0522-1] [PMID: 27257436]
[http://dx.doi.org/10.1016/j.biortech.2012.04.100] [PMID: 22705958]
[http://dx.doi.org/10.1002/biot.200900279] [PMID: 20213636]
[http://dx.doi.org/10.1007/s12010-012-9593-z] [PMID: 22434350]
[http://dx.doi.org/10.1016/S0922-338X(97)82052-1]
[http://dx.doi.org/10.1016/j.biortech.2007.03.053] [PMID: 17531470]
[http://dx.doi.org/10.1080/10826068.2013.829497] [PMID: 24320235]
[http://dx.doi.org/10.1021/ie50674a007]
[http://dx.doi.org/10.1198/TECH.2010.09113]
[http://dx.doi.org/10.1111/j.1472-765X.2004.01622.x] [PMID: 15548307]
[http://dx.doi.org/0.1080/00021369.1984.10866596]
[http://dx.doi.org/10.1046/j.1365-2672.1999.00560.x] [PMID: 10389264]
[http://dx.doi.org/10.1002/1521-3846(200207)22:3/4<355:AID-ABIO355>3.0.CO;2-6]