Application of Ionic Liquids in Biotechnology

343 Pages·2019·12.396 MB·English

by  Toshiyuki Itoh, Yoon-Mo Koo

Advances in Biochemical Engineering/Biotechnology 168
Series Editor: T. Scheper
Toshiyuki Itoh
Yoon-Mo Koo Editors
Application of
Ionic Liquids in
Biotechnology
168
Advances in Biochemical
Engineering/Biotechnology
SeriesEditor
T.Scheper,Hannover,Germany
EditorialBoard
S.Belkin,Jerusalem,Israel
T.Bley,Dresden,Germany
J.Bohlmann,Vancouver,Canada
M.B.Gu,Seoul,Korea(Republicof)
W.-S.Hu,Minneapolis,USA
B.Mattiasson,Lund,Sweden
J.Nielsen,Gothenburg,Sweden
H.Seitz,Potsdam,Germany
R.Ulber,Kaiserslautern,Germany
A.-P.Zeng,Hamburg,Germany
J.-J.Zhong,Shanghai,China
W.Zhou,Shanghai,China
Aims and Scope
This book series reviews current trends in modern biotechnology and biochemical
engineering. Its aim is to cover all aspects of these interdisciplinary disciplines,
whereknowledge,methodsandexpertisearerequiredfromchemistry,biochemistry,
microbiology,molecularbiology,chemicalengineeringandcomputerscience.
Volumes are organized topically and provide a comprehensive discussion of
developments in the field over the past 3–5 years. The series also discusses new
discoveries and applications. Special volumes are dedicated to selected topics
whichfocusonnewbiotechnologicalproductsandnewprocessesfortheirsynthesis
andpurification.
In general, volumes are edited by well-known guest editors. The series editor and
publisher will, however, always be pleased to receive suggestions and supplemen-
taryinformation.ManuscriptsareacceptedinEnglish.
In references, Advances in Biochemical Engineering/Biotechnology is abbreviated
asAdv.Biochem.Engin./Biotechnol.andcitedasajournal.
Moreinformationaboutthisseriesathttp://www.springer.com/series/10
(cid:129)
Toshiyuki Itoh Yoon-Mo Koo
Editors
Application of Ionic Liquids
in Biotechnology
With contributions by
(cid:1) (cid:1) (cid:1) (cid:1)
D. C. V. Belchior C.-W. Cho I. F. Duarte M. G. Freire
(cid:1) (cid:1) (cid:1) (cid:1) (cid:1)
K. Fujita M. Goto T. Itoh Y.-M. Koo S. H. Lee
(cid:1) (cid:1) (cid:1) (cid:1)
N. L. Mai M. Moniruzzaman K. K. Oh H. Ohno
(cid:1) (cid:1) (cid:1) (cid:1)
S. Park T. P. T. Pham R. D. Rogers J. L. Shamshina
(cid:1) (cid:1) (cid:1) (cid:1)
M.-H. Song T. Usuki Z. Yang M. Yoshizawa-Fujita
(cid:1)
Y.-S. Yun O. Zavgorodnya
Editors
ToshiyukiItoh Yoon-MoKoo
CenterforResearchonGreenSustainable DepartmentofBiologicalEngineering,
Chemistry,GraduateSchoolof CollegeofEngineering
Engineering InhaUniversity
TottoriUniversity Incheon,Korea(Republicof)
Tottori,Japan
ISSN0724-6145 ISSN1616-8542 (electronic)
AdvancesinBiochemicalEngineering/Biotechnology
ISBN978-3-030-23080-7 ISBN978-3-030-23081-4 (eBook)
https://doi.org/10.1007/978-3-030-23081-4
©SpringerNatureSwitzerlandAG2019
Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartofthe
materialisconcerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,
broadcasting,reproductiononmicrofilmsorinanyotherphysicalway,andtransmissionorinformation
storageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilarmethodology
nowknownorhereafterdeveloped.
Theuseofgeneraldescriptivenames,registerednames,trademarks,servicemarks,etc.inthispublication
doesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevant
protectivelawsandregulationsandthereforefreeforgeneraluse.
The publisher, the authors, and the editorsare safeto assume that the adviceand informationin this
bookarebelievedtobetrueandaccurateatthedateofpublication.Neitherthepublishernortheauthorsor
theeditorsgiveawarranty,expressorimplied,withrespecttothematerialcontainedhereinorforany
errorsoromissionsthatmayhavebeenmade.Thepublisherremainsneutralwithregardtojurisdictional
claimsinpublishedmapsandinstitutionalaffiliations.
ThisSpringerimprintispublishedbytheregisteredcompanySpringerNatureSwitzerlandAG.
Theregisteredcompanyaddressis:Gewerbestrasse11,6330Cham,Switzerland
Preface
A Short Glance into the Past
Ionic liquids (ILs) are the less volatile, less flammable, less toxic so-called “room
temperature molten salts” encompassing a unique solubility for organic and inor-
ganic materials. The history of research on ILs is very interesting. The first room
temperature molten salt, ethylammonium nitrate, was reported in 1904, more than
100yearsago![1].However,noattentionwasgiventowardsimilarsaltsforthenext
75 years. In 1979, Robinson et al. investigated the electrochemical properties and
spectroscopic behavior of a number of aromatic hydrocarbons in the
low-temperature molten salt system of AlCl -n-butylpyridinium chloride [2]. In
3
1986,Wilkesandhiscoworkersdemonstratedthefirstorganicreaction,theFriedel–
Crafts reaction, using the same salt as both the solvent and the catalyst [3]. Since
these ILs were moisture-sensitive compounds, these reports were unable to trigger
any further IL chemistry. In 1992, the air and moisture stable IL, 1-ethyl-3-
methylimidazolium tetrafluoroborate ([Bmim][BF ]), was synthesized by Wilkes
4
[4], and Dupont prepared the moisture stable hydrophobic IL 1-butyl-3-
methylimidazolium hexafluorophosphate ([Bmim][PF ]) in 1996 [5]. This was
6
followed by a milestone paper presented by Seddon and coworkers in 1999 [6];
the authors demonstrated the Heck reaction using an IL and clearly indicated the
meritofILsassolventsfororganicreactions.Inthesameyear,Weltonpresentedthe
firstreviewofILs[7]whereinhedefinedthecompoundsthatshouldbecategorized
as ILs. These papers triggered the eruption of IL chemistry even in the field of
biotechnology.ThefirstthreeexamplesofbiotransformationinILswerereportedin
2000 [8–10]; since then, ILs have been implicated in numerous applications in the
fieldofbioscience andbiotechnology,and thenumber ofpapers has reached more
than7,000inthelasttwodecades[NumberofpublicationsinthefieldofILsfrom
1975–2018(searchedby“WebofScience”,onMarch27,2018).84,796references
are listed for the topic of “ionic liquid(cid:3)” in 99 fields of the database of Web of
Science Core Collections of THOMSON REUTERS, Ltd.]. The science of ILs is
considered as one of the highlights in modern chemistry, with 86,000 papers
v
vi Preface
publishedbythisyearduetothewideapplicationofILsinvariousfields[Numberof
publicationsinthefieldofILsfrom1975–2018(searchedby“WebofScience”,on
March 27, 2018). 84,796 references are listed for the topic of “ionic liquid(cid:3)” in
99 fields of the database of Web of Science Core Collections of THOMSON
REUTERS,Ltd.].
Today and Future
The usages ofILsinbiotechnologyarenotlimitedto theirapplication assolvents/
cosolvents for enzyme or whole-cell catalyzed reactions but have extended to
various fields such as solvents/agents for extraction, isolation, and processing of
naturaloriginatedcompounds(e.g.,biopolymers,activepharmaceuticalingredients,
protein). In addition, to overcome the concerns regarding the environment and
toxicity of using IL in biological processes, many studies investigated the toxicity
mechanism and focused on the development of a new generation of ILs derived
totally from nature, which are inexpensive, biocompatible, and biodegradable with
lowtoxicity.ThesenewILshavethepotentialasalternativesforfossiloriginatedILs
in many biological applications as well as being used as the active pharmaceutical
ingredientsinbiomedicalapplications[11].BasedontheexpectationsthatILsmay
produceabreakthroughinthefieldsofbiotechnology,thisbookpresentsthecurrent
stateoftheartinenvironmentallybenignbiotechnologyusingILengineering,such
as application in the reaction media for biotransformation, stabilization and activa-
tionofbiocatalysts,bioseparationprocesses,pretreatmentofbiomassforenzymatic
reactions, synthesis of biopolymer-based hydrogels, isolation of medicinal com-
pounds from bioresources, environmental concerns of ILs in biotechnical applica-
tions, and the development of ILs and their derivatives from nature. Compared to
conventionalsolvents,theuniquepropertiesofILshaveunlockedawiderangefor
their applications in biotechnology. This book contains a number of trailblazing
reviewsthatdescribethepowerofILsinbiotechnologyanddiscussthefieldswhere
investigationsneedtobefocusedforutilizingILsinbiotechnology.Webelievethis
bookwillaidyouinacquiringideasforfutureresearchinthefieldofbiotechnology.
Tottori,Japan ToshiyukiItoh
Incheon,Korea(Republicof) Yoon-MoKoo
References
1. Walden P (1914) Ueber die Molekulargrösse und elektriseche Leitfähigkeit
eungergeschmoltezenenSalze.BullAcadImperSci(St.Petersburg),405–422
2. RobinsonJ,OsteryoungRA(1979)Anelectrochemicalandspectroscopicstudy
of some aromatic hydrocarbons in the room temperature molten salt system
aluminumchloride-n-butylpyridiniumchloride.JAmChemSoc101:323–327
Preface vii
3. Boon JB, Levisky JA, Pflug L, Wilkes JS (1986) Friedel–Crafts reactions in
ambient-temperaturemoltensalts.JOrgChem51:480–483
4. Wilkes JS, Zaworotko M (1992) Air and water stable 1-ethyl-3-
methylimidazoliumbasedionicliquids.JChemSocChemCommun,965–966
5. SuarezPAZ,DulliusJEL,SandraE,DeSouzaRF,DupontJ(1996)Theuseof
new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium
complexes.Polyhedron15:1217–1219
6. CarmichaelAJ,EarleMJ,HolbreyJD,McCormacPB,SeddonKR(1999)The
Heck reaction in ionic liquids:a multiphasic catalyst system. Org Lett
1:997–1000
7. Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and
catalysis.ChemRev99:2071–2084
8. Cull SG, Holbre JD, Vargas-Mora V, Seddon KR, Lye GJ (2000) Room-
temperature ionic liquids as replacements for organic solvents in multiphase
bioprocessoperations.BiotechnolBioeng69:227–237
9. Erbeldinger M, Mesiano AJ, Russell AJ (2000) Enzymatic catalysis of forma-
tion of Z-aspartame in ionic liquid – an alternative to enzymatic catalysis in
organicsolvents.BiotechnolProg16:1129–1131
10. Lau RM, van Rantwijk F, Seddon KR, Sheldon RA (2000) Lipase-catalyzed
reactionsinionicliquids.OrgLett2:4189–4191
11. Egorova KS, Gordeev EG, Ananikov VP (2017) Biological activity of ionic
liquids and their application in pharmaceutics and medicine. Chem Rev
117:7132–7189
Contents
IonicLiquidsinBioseparationProcesses. . . . . . . . . . . . . . . . . . . . . . . . 1
DianaC.V.Belchior,IolaF.Duarte,andMaraG.Freire
NaturalDeepEutecticSolventsandTheirApplications
inBiotechnology. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
ZhenYang
IonicLiquidPretreatmentofLignocellulosicBiomassforEnhanced
EnzymaticDelignification. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61
MuhammadMoniruzzamanandMasahiroGoto
ActivationofLipase-CatalyzedReactionsUsingIonicLiquids
forOrganicSynthesis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 79
ToshiyukiItoh
Whole-CellBiocatalysisinIonicLiquids. . .. . . . . . .. . . . . . .. . . . . . .. 105
NgocLanMaiandYoon-MoKoo
Biopolymer-BasedCompositeMaterialsPreparedUsingIonic
Liquids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 133
SaeromPark,KyeongKeunOh,andSangHyunLee
AdvancesinProcessingChitinasaPromisingBiomaterialfrom
IonicLiquids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 177
JuliaL.Shamshina,OleksandraZavgorodnya,andRobinD.Rogers
SynthesisofIonicLiquidsOriginatedfromNaturalProducts. . . . . .. . . 199
HiroyukiOhno
IonicLiquidsasStabilizationandRefoldingAdditivesandSolvents
forProteins. . . .. . . .. . . .. . . . .. . . .. . . .. . . .. . . .. . . .. . . . .. . . .. 215
KyokoFujita
ix
x Contents
ExtractionandIsolationofNaturalOrganicCompoundsfromPlant
LeavesUsingIonicLiquids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 227
ToyonobuUsukiandMasahiroYoshizawa-Fujita
EnvironmentalConcernsRegardingIonicLiquidsinBiotechnological
Applications. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 241
Chul-WoongCho,Myung-HeeSong,ThiPhuongThuyPham,
andYeoung-SangYun
Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 329