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Glucose
FromWikipedia,thefreeencyclopedia

GlucoseisasugarwiththemolecularformulaC6H12O6.Thename"glucose"(/lukoz/,/lukos/)comes

DGlucose

fromtheGreekword,meaning"sweetwine,must".[3]Thesuffix"ose"isachemicalclassifier,denotinga
carbohydrate.Itisalsoknownasgrapesugar.With6carbonatoms,itisclassedasahexose,asubcategoryof
monosaccharides.Dglucoseisoneofthe16aldohexosestereoisomers.TheDisomer(Dglucose),alsoknown
asdextrose,occurswidelyinnature,buttheLisomer(Lglucose)doesnot.Glucoseismadeduring
photosynthesisfromwaterandcarbondioxide,usingenergyfromsunlight.Thereverseofthephotosynthesis
reaction,whichreleasesthisenergy,isaveryimportantsourceofpowerforcellularrespiration.Glucoseisstored
asapolymer,inplantsasstarchandinanimalsasglycogen,fortimeswhentheorganismwillneedit.Glucose
circulatesinthebloodofanimalsasbloodsugar.Glucosecanbeobtainedbyhydrolysisofcarbohydratessuchas
milk,canesugar,maltose,cellulose,glycogenetc.Itishowever,manufacturedbyhydrolysisofcornstarchby
steaminganddilutingacid.[4]

Dglucopyranose(chairform)

Contents
1 Functioninbiology
1.1 Analyteinmedicalbloodtest
1.2 Energysource
1.3 Glycolysis
1.4 Precursor
2 Structureandnomenclature
2.1 Openchainform
2.2 Cyclicforms
2.3 Rotationalisomers
3 Physicalproperties
3.1 Solutions
3.2 Solidstate
3.3 Opticalactivity
3.4 ComputationalModels
4 Production
4.1 Biosynthesis
4.2 Commercial
5 Sourcesandabsorption
5.1 Glucoseindiabetes
5.2 Inhypoglycemiamanagement
6 History
7 Seealso
8 References
9 Externallinks

HaworthprojectionofDglucopyranose

FischerprojectionofDglucose
Names
PreferredIUPACname
D Glucose
SystematicIUPACname
(2R,3S,4R,5R)2,3,4,5,6Pentahydroxyhexanal
Othernames
Bloodsugar
Dextrose
Cornsugar
D Glucose
Grapesugar
Identifiers
CASNumber

Functioninbiology
Glucoseisthemostwidelyusedaldohexoseinlivingorganisms.Onepossibleexplanationforthisisthatglucose
hasalowertendencythanotheraldohexosestoreactnonspecificallywiththeaminegroupsofproteins.[5]This
reactionglycationimpairsordestroysthefunctionofmanyproteins.[5]Glucose'slowrateofglycationcanbe
attributedtoithavingamorestablecyclicformcomparedtootheraldohexoses,whichmeansitspendslesstime
thantheydoinitsreactiveopenchainform.[5]Thereasonforglucosehavingthemoststablecyclicformofallthe
aldohexosesisthatitshydroxygroups(withtheexceptionofthehydroxygroupontheanomericcarbonofD
glucose)areintheequatorialposition.Manyofthelongtermcomplicationsofdiabetes(e.g.,blindness,renal
failure,andperipheralneuropathy)areprobablyduetotheglycationofproteinsorlipids.[6]Incontrast,enzyme
regulatedadditionofsugarstoproteiniscalledglycosylationandisessentialforthefunctionofmanyproteins.[7]

px?ref=50997)
3DMet

B04623(http://www.3dmet.dn
a.affrc.go.jp/cgi/show_data.ph
p?acc=B04623)

Abbreviations

Glc

BeilsteinReference

1281604

ChEBI

CHEBI:4167(https://www.ebi.a
c.uk/chebi/searchId.do?chebiId
=4167)

ChEMBL

Analyteinmedicalbloodtest
Glucoseisacommonmedicalanalytemeasuredinbloodsamples.Eatingorfastingpriortotakingabloodsample
hasaneffectontheresult.Ahighfastingglucosebloodsugarlevelmaybeasignofprediabetesordiabetes
mellitus.

Energysource
https://en.wikipedia.org/wiki/Glucose

50997(http://www.commonc
hemistry.org/ChemicalDetail.as

ChEMBL1222250(https://ww
w.ebi.ac.uk/chembldb/index.ph
p/compound/inspect/ChEMBL1
222250)

ChemSpider

5589(http://www.chemspider.
com/ChemicalStructure.5589.
html)

ECNumber

2000751

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Glucoseisaubiquitousfuelinbiology.Itisusedasanenergysourceinmostorganisms,frombacteriatohumans,
througheitheraerobicrespiration,anaerobicrespiration,orfermentation.Glucoseisthehumanbody'skeysource
ofenergy,throughaerobicrespiration,providingabout3.75kilocalories(16kilojoules)offoodenergyper
gram.[8]Breakdownofcarbohydrates(e.g.starch)yieldsmonoanddisaccharides,mostofwhichisglucose.
Throughglycolysisandlaterinthereactionsofthecitricacidcycleandoxidativephosphorylation,glucoseis
oxidizedtoeventuallyformCO2andwater,yieldingenergymostlyintheformofATP.Theinsulinreaction,and
othermechanisms,regulatetheconcentrationofglucoseintheblood.

GmelinReference

83256

IUPHAR/BPS

4536(http://www.guidetophar
macology.org/GRAC/LigandDis
playForward?tab=summary&lig
andId=4536)

Jmol3Dmodel

Interactiveimage(http://chema
pps.stolaf.edu/jmol/jmol.php?m
odel=OC%5BC%40H%5D1O
C%28O%29%5BC%40H%5
D%28O%29%5BC%40%40H%
5D%28O%29%5BC%40%40
H%5D1O)
Interactiveimage(http://chema
pps.stolaf.edu/jmol/jmol.php?m
odel=C%28%5BC%40%40H%
5D1%5BC%40H%5D%28%5B
C%40%40H%5D%28%5BC%4
0H%5D%28%5BC%40H%5
D%28O1%29O%29O%29O%2
9O%29O)

KEGG

C00031(http://www.kegg.jp/en

Glucosesuppliesalmostalltheenergyforthebrain,[9]soitsavailabilityinfluencespsychologicalprocesses.When
glucoseislow,psychologicalprocessesrequiringmentaleffort(e.g.,selfcontrol,effortfuldecisionmaking)are
impaired.[10][11][12][13]

Glycolysis
DGlucose

Hexokinase

DGlucose6
phosphate

ATP ADP

try/C00031)
MeSH

Glucose(https://www.nlm.nih.
gov/cgi/mesh/2014/MB_cgi?mo
de=&term=Glucose)

PubChem

5793(https://pubchem.ncbi.nl
m.nih.gov/compound/5793)

RTECSnumber

LZ6600000

UNII

5SL0G7R0OK(http://fdasis.nl
m.nih.gov/srs/srsdirect.jsp?reg

CompoundC00031(http://www.genome.jp/dbgetbin/www_bget?compound+C00031)at

KEGGPathwayDatabase. Enzyme2.7.1.1(http://www.genome.jp/dbgetbin/www_bget?

enzyme+2.7.1.1)atKEGGPathwayDatabase. CompoundC00668(http://www.genome.j

p/dbgetbin/www_bget?compound+C00668)atKEGGPathwayDatabase. Reaction
R01786(http://www.genome.jp/dbgetbin/www_bget?rn+R01786)atKEGGPathway

no=5SL0G7R0OK)

Database.

Useofglucoseasanenergysourceincellsisbyeitheraerobicrespiration,anaerobicrespiration,orfermentation.
Alloftheseprocessesfollowfromanearliermetabolicpathwayknownasglycolysis.Thefirststepofglycolysisis
thephosphorylationofglucosebyahexokinasetoformglucose6phosphate.Themainreasonfortheimmediate
phosphorylationofglucoseistopreventitsdiffusionoutofthecellasthechargedphosphategroupprevents
glucose6phosphatefromeasilycrossingthecellmembrane.Furthermore,additionofthehighenergyphosphate
groupactivatesglucoseforsubsequentbreakdowninlaterstepsofglycolysis.Atphysiologicalconditionsthis
initialreactionisirreversible.

InChI

Inanaerobicrespiration,oneglucosemoleculeproducesanetgainoftwoATPmolecules(fourATPmolecules
areproducedduringglycolysis,buttwoarerequiredbyenzymesusedduringtheprocess).[14]Inaerobic
respiration,amoleculeofglucoseismuchmoreprofitableinthatamaximumnetproductionof30or32ATP
molecules(dependingontheorganism)isgenerated.[15]
Clickongenes,proteinsandmetabolitesbelowtolinktorespectivearticles.[1]

SMILES

Properties
Chemicalformula

C6H12O6

Molarmass

180.16gmol1

Appearance

Whitepowder

Density

1.54g/cm3

Meltingpoint

D glucose:146C(295F
419K)
D glucose:150C(302F
423K)

Solubilityinwater

909g/1L(25C(77F))

Dipolemoment

8.6827
Thermochemistry

Specific
heatcapacity(C)

218.6JK1mol1[1]

Stdmolar
entropy(So298)

209.2JK1mol1[1]

Stdenthalpyof
1271kJ/mol [2]
formation(fHo298)
Stdenthalpyof
combustion
(cHo298)

2805kJ/mol

Pharmacology
ATCcode

https://en.wikipedia.org/wiki/Glucose

B05CX01(WHO(http://www.
whocc.no/atc_ddd_index/?code
=B05CX01))V04CA02(WHO
(http://www.whocc.no/atc_ddd

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_index/?code=V04CA02)),
V06DC01(WHO(http://www.
whocc.no/atc_ddd_index/?code
=V06DC01))
Hazards
Safetydatasheet

ICSC0865(http://www.inche
m.org/documents/icsc/icsc/eics
0865.htm)

NFPA704

Exceptwhereotherwisenoted,dataaregivenfor
materialsintheirstandardstate(at25C[77F],
100kPa).
verify(whatis

?)

Infoboxreferences

GlycolysisandGluconeogenesisedit(http://www.wikipathways.
org/index.php/Pathway:WP534)

1.TheinteractivepathwaymapcanbeeditedatWikiPathways:"GlycolysisGluconeogenesis_WP534".

Precursor
Organismsuseglucoseasaprecursorforthesynthesisofseveralimportantsubstances.Starch,cellulose,andglycogen
("animalstarch")arecommonglucosepolymers(polysaccharides).Someofthesepolymers(starchorglycogen)serveas
energystores,whileothers(celluloseandchitin,whichismadefromaderivativeofglucose)havestructuralroles.
Oligosaccharidesofglucosecombinedwithothersugarsserveasimportantenergystores.Theseincludelactose,the
predominantsugarinmilk,whichisaglucosegalactosedisaccharide,andsucrose,anotherdisaccharidewhichiscomposed
ofglucoseandfructose.Glucoseisalsoaddedontocertainproteinsandlipidsinaprocesscalledglycosylation.Thisisoften
criticalfortheirfunctioning.Theenzymesthatjoinglucosetoothermoleculesusuallyusephosphorylatedglucosetopower
theformationofthenewbondbycouplingitwiththebreakingoftheglucosephosphatebond.
Otherthanitsdirectuseasamonomer,glucosecanbebrokendowntosynthesizeawidevarietyofotherbiomolecules.This
isimportant,asglucoseservesbothasaprimarystoreofenergyandasasourceoforganiccarbon.Glucosecanbebroken
downandconvertedintolipids.ItisalsoaprecursorforthesynthesisofotherimportantmoleculessuchasvitaminC
(ascorbicacid).

Glucosemetabolismandvarious
formsofitintheprocess
Glucosecontainingcompoundsand
isomericformsaredigestedandtaken
upbythebodyintheintestines,
includingstarch,glycogen,
disaccharidesandmonosaccharides.
Glucoseisstoredinmainlytheliver
andmusclesasglycogen.
Itisdistributedandusedintissuesas
freeglucose.

Structureandnomenclature
GlucoseisamonosaccharidewithformulaC6H12O6orH(C=O)(CHOH)5H,whosefivehydroxyl(OH)groupsarearrangedinaspecificwayalongitssixcarbon
back.

Openchainform
Initsfleetingopenchainform,theglucosemoleculehasanopen(asopposedtocyclic)andunbranched
backboneofsixcarbonatoms,C1throughC6whereC1ispartofanaldehydegroupH(C=O),and
eachoftheotherfivecarbonsbearsonehydroxylgroupOH.Theremainingbondsofthebackbone
carbonsaresatisfiedbyhydrogenatomsH.Therefore,glucoseisbothahexoseandanaldose,oran
aldohexose.ThealdehydegroupmakesglucoseareducingsugargivingapositivereactionwiththeFehling
test.

DGlucosein
Fischer
projection

EachofthefourcarbonsC2throughC5isastereocenter,meaningthatitsfourbondsconnecttofour
differentsubstituents.(CarbonC2,forexample,connectsto(C=O)H,OH,H,and(CHOH)4H.)In
Dglucose,thesefourpartsmustbeinaspecificthreedimensionalarrangement.Namely,whenthe
moleculeisdrawnintheFischerprojection,thehydroxylsonC2,C4,andC5mustbeontherightside,
whilethatonC3mustbeontheleftside.

Glucosecanexistinbotha
straightchainandringform.

ThepositionsofthosefourhydroxylsareexactlyreversedintheFischerdiagramofLglucose.DandLglucosearetwoofthe16possible
aldohexosestheother14areallose,altrose,mannose,gulose,idose,galactose,andtalose,eachwithtwoenantiomers,"D"and"L".

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Thealdehydeformof
glucose

Itisimportanttonotethatthelinearformofglucosemakesuplessthan3%oftheglucosemoleculesinawatersolution.Therestisoneoftwocyclicformsofglucose
thatareformedwhenthehydroxylgrouponcarbon5(C5)bondstothealdehydecarbon1(C1).[16]

Cyclicforms
Insolutions,theopenchainformofglucose(either"D"or"L")existsinequilibriumwithseveralcyclicisomers,eachcontainingaringofcarbonsclosedbyone
oxygenatom.Inaqueoussolutionhowever,morethan99%ofglucosemolecules,atanygiventime,existaspyranose.Theopenchainformislimitedtoabout0.25%
andfuranoseexistsinnegligibleamounts.Theterms"glucose"and"Dglucose"aregenerallyusedforthesecyclicformsaswell.Theringarisesfromtheopenchain
formbyanucleophilicadditionreactionbetweenthealdehydegroup(C=O)HatC1andthehydroxylgroupOHatC4orC5,yieldingahemiacetalgroup
C(OH)HO.
ThereactionbetweenC1andC5createsamoleculewithasixmemberedring,calledpyranose,afterthecyclicetherpyran,thesimplestmoleculewiththesame
carbonoxygenring.The(muchrarer)reactionbetweenC1andC4createsamoleculewithafivememberedring,calledfuranose,afterthecyclicetherfuran.In
eithercase,eachcarbonintheringhasonehydrogenandonehydroxylattached,exceptforthelastcarbon(C4orC5)wherethehydroxylisreplacedbythe
remainderoftheopenmolecule(whichis(C(CH2OH)HOH)Hor(CHOH)H,respectively).
TheringclosingreactionmakescarbonC1chiral,too,sinceitsfourbondsleadtoH,toOH,tocarbonC2,andtotheringoxygen.Thesefourpartsofthe
moleculemaybearrangedaroundC1(theanomericcarbon)intwodistinctways,designatedbytheprefixes""and"".Whenaglucopyranosemoleculeisdrawn
intheHaworthprojection,thedesignation""meansthatthehydroxylgroupattachedtoC1andtheCH2OHgroupatC5liesonoppositesidesofthering'splane
(atransarrangement),while""meansthattheyareonthesamesideoftheplane(acisarrangement).
Therefore,theopenchainisomerDglucosegivesrisetofourdistinctcyclicisomers: Dglucopyranose, Dglucopyranose, Dglucofuranose,and D
glucofuranose.Theseareallchiral.

D
Glucopyranose

D
Glucopyranose

D
Glucofuranose

D
Glucofuranose

D
Glucopyranose

D
Glucopyranose

TheotheropenchainisomerLglucosesimilarlygivesrisetofourdistinctcyclicformsofLglucose,eachthemirrorimageofthecorrespondingDglucose.
Theringsarenotplanar,butaretwistedinthreedimensions.Theglucopyranosering(or)canassumeseveralnonplanarshapes,analogoustothe"chair"and"boat"
conformationsofcyclohexane.Similarly,theglucofuranoseringmayassumeseveralshapes,analogoustothe"envelope"conformationsofcyclopentane.
Theglucopyranoseformsofglucosepredominateinsolution,andaretheonlyformsobservedinthesolidstate.Theyarecrystallinecolorlesssolids,highlysolublein
waterandaceticacid,poorlysolubleinmethanolandethanol.Theymeltat146C(295F)()and150C(302F)(),anddecomposeathighertemperaturesinto
carbonandwater.

Rotationalisomers

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Eachglucoseisomerissubjecttorotationalisomerism.Withinthecyclicformofglucose,rotationmayoccuraroundtheO6
C6C5O5torsionangle,termedtheangle,toformthreestaggeredrotamerconformationscalledgauchegauche(gg),
gauchetrans(gt)andtransgauche(tg).Formethyl Dglucopyranoseatequilibriumtheratioofmoleculesineach
rotamerconformationisreportedas57:38:5gg:gt:tg.[17]Thistendencyfortheangletoprefertoadoptagauche
conformationisattributedtothegaucheeffect.

Physicalproperties
Solutions

Widelyproposedarrowpushing
mechanismforacidcatalyzed
dynamicequilibriumbetweend
glucoseanddglucose

Allformsofglucosearecolorlessandeasilysolubleinwater,aceticacid,andseveralothersolvents.Theyareonlysparingly
solubleinmethanolandethanol.
Theopenchainformisthermodynamicallyunstable,anditspontaneouslyisomerizestothecyclicforms.(Althoughthering
closurereactioncouldintheorycreatefourorthreeatomrings,thesewouldbehighlystrained,andarenotobservedin
practice.)Insolutionsatroomtemperature,thefourcyclicisomersinterconvertoveratimescaleofhours,inaprocesscalled
mutarotation.[18]Startingfromanyproportions,themixtureconvergestoastableratioof:36:64.Theratiowouldbe:
11:89ifitwerenotfortheinfluenceoftheanomericeffect.[19]Mutarotationisconsiderablyslowerattemperaturescloseto
0C(32F).
Mutarotationconsistsofatemporaryreversaloftheringformingreaction,resultingintheopenchainform,followedbya
Glucose5%
reformingofthering.TheringclosurestepmayuseadifferentOHgroupthantheonerecreatedbytheopeningstep(thus
switchingbetweenpyranoseandfuranoseforms),and/orthenewhemiacetalgroupcreatedonC1mayhavethesameor
oppositehandednessastheoriginalone(thusswitchingbetweentheandforms).Thus,thoughtheopenchainformisbarelydetectableinsolution,itisanessential
componentoftheequilibrium.

Solidstate
Dependingonconditions,threemajorsolidformsofglucosecanbecrystallisedfromwatersolutions:glucopyranose,glucopyranose,andglucopyranose
hydrate.[20]

Opticalactivity
Whetherinwaterorinthesolidform,Dglucoseisdextrorotatory,meaningitwillrotatethedirectionofpolarizedlightclockwise.Theeffectisduetothechiralityofthe
molecules,andindeedthemirrorimageisomer,Lglucose,islevorotatory(rotatespolarizedlightcounterclockwise)bythesameamount.Thestrengthoftheeffectis
differentforeachofthefivetautomers.
NotethattheDprefixdoesnotreferdirectlytotheopticalpropertiesofthecompound.ItindicatesthattheC2chiralcenterhasthesamehandednessasthatofD
glyceraldehyde(whichwassolabeledbecauseitisdextrorotatory).ThefactthatDglucoseisdextrorotatoryisacombinedeffectofitsfourchiralcenters,notjustof
C2andindeedsomeoftheotherDaldohexosesarelevorotatory.

ComputationalModels
Glucosephysicalandchemicalpropertieshavebeenusedtobuildacomputationalmodelofproteinglucosebindingsites.[21]

Production
Metabolismofcommonmonosaccharidesandsomebiochemicalreactionsofglucose

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Biosynthesis
Inplantsandsomeprokaryotes,glucoseisaproductofphotosynthesis.Inanimalsandfungi,glucoseresultsfromthebreakdownofglycogen,aprocessknownas
glycogenolysis.Inplantsthebreakdownsubstrateisstarch.
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Inanimals,glucoseissynthesizedintheliverandkidneysfromnoncarbohydrateintermediates,suchaspyruvate,lactateandglycerol,byaprocessknownas
gluconeogenesis.
Insomedeepseabacteria,glucoseisproducedbychemosynthesis.

Commercial
Glucoseisproducedcommerciallyviatheenzymatichydrolysisofstarch.Manycropscanbeusedasthesourceofstarch.Maize,rice,wheat,cassava,cornhuskand
sagoareallusedinvariouspartsoftheworld.IntheUnitedStates,cornstarch(frommaize)isusedalmostexclusively.Mostcommercialglucoseoccursasa
componentofinvertsugar,aroughly1:1mixtureofglucoseandfructose.Inprinciple,cellulosecouldbehydrolysedtoglucose,butthisprocessisnotyetcommercially
practical.[20]Fructosehasapproximately75%thesweetnessofsucrose(tablesugar).[22]Glucosesyrupisalsoknownascornsyrupandisessentiallyapurified
aqueoussolutionofsaccharidesthatareobtainedfromediblestarchthathaveadextroseequivalencyof20ormore.Driedcornsyrupisglucosesyrupwiththewater
removedfromit.GlucosehasaDEof100andMaltodextrinswhichisthedriedproductofsaccharideshasaDEoflessthan20.ThesyrupitselfhasaDEbetween20
and95.[23]

Sourcesandabsorption
Mostdietarycarbohydratescontainglucose,eitherastheironlybuildingblock,asinstarchandglycogen,ortogetherwithanothermonosaccharide,asinsucroseand
lactose.
Inthelumenoftheduodenumandsmallintestine,theglucoseoligoandpolysaccharidesarebrokendowntomonosaccharidesbythepancreaticandintestinal
glycosidases.Otherpolysaccharidescannotbeprocessedbythehumanintestineandrequireassistancebyintestinalfloraiftheyaretobebrokendownthemost
notableexceptionsaresucrose(fructoseglucose)andlactose(galactoseglucose).Glucoseisthentransportedacrosstheapicalmembraneoftheenterocytesby
SLC5A1(SGLT1),andlateracrosstheirbasalmembranebySLC2A2(GLUT2).[24]Someoftheglucoseisconvertedtolacticacidbyastrocytes,whichisthen
utilizedasanenergysourcebybraincellssomeoftheglucoseisusedbyintestinalcellsandredbloodcells,whiletherestreachestheliver,adiposetissueandmuscle
cells,whereitisabsorbedandstoredasglycogen(undertheinfluenceofinsulin).Livercellglycogencanbeconvertedtoglucoseandreturnedtothebloodwheninsulin
isloworabsentmusclecellglycogenisnotreturnedtothebloodbecauseofalackofenzymes.Infatcells,glucoseisusedtopowerreactionsthatsynthesizesomefat
typesandhaveotherpurposes.Glycogenisthebody's"glucoseenergystorage"mechanism,becauseitismuchmore"spaceefficient"andlessreactivethanglucose
itself.

Glucoseindiabetes
Diabetesisametabolicdisorderwherethebodyisunabletoregulatelevelsofglucoseinthebloodbecauseoflackofinsulin
inthebody.Insulinisahormonethatregulatesglucoselevels,allowingthebody'scellstoabsorbanduseglucose.Withoutit,
glucosecannotenterthecellandthereforecannotbeusedasfuelforthebody'sfunctions.[25]Glucoselevelscanalsobe
testedusingmultiplemethods,suchasthefastingglucosetestwhichmeasuresthelevelofglucoseinthebloodafter8hoursof
fasting.Anothertestisthe2hourglucosetolerancetest(GTT)forthistest,thepersonhasafastingglucosetestdone,then
drinksa75gramglucosedrinkandisretested.Thistestmeasurestheabilityoftheperson'sbodytoprocessglucose.Over
timethebloodglucoselevelsshoulddecreaseasinsulinallowsittobetakenupbycellsandexitthebloodstream.[26]

Glucosetablets

Inhypoglycemiamanagement
Individualswithdiabetesorotherconditionswherehypoglycemia(lowbloodsugar)mayoccur,oftencarrysmallamountsofsugarinvariousforms.Onesugar
commonlyusedisglucose,oftenintheformofglucosetablets(glucosepressedintoatabletshapesometimeswithoneormoreotheringredientsasabinder),hard
candy,orsugarpacket.

History
Glucosewasfirstisolated(fromraisins)in1747bytheGermanchemistAndreasMarggraf.[27]Becauseglucoseisabasicnecessityofmanyorganisms,acorrect
understandingofitschemicalmakeupandstructurecontributedgreatlytoageneraladvancementinorganicchemistry.Thisunderstandingoccurredlargelyasaresultof
theinvestigationsofEmilFischer,aGermanchemistwhoreceivedthe1902NobelPrizeinChemistryforhisfindings.[28]Thesynthesisofglucoseestablishedthe
structureoforganicmaterialandconsequentlyformedthefirstdefinitivevalidationofJacobusHenricusvan'tHoff'stheoriesofchemicalkineticsandthearrangements
ofchemicalbondsincarbonbearingmolecules.[29]Between1891and1894,Fischerestablishedthestereochemicalconfigurationofalltheknownsugarsandcorrectly
predictedthepossibleisomers,applyingvan'tHoff'stheoryofasymmetricalcarbonatoms.

Seealso
2,5Dimethylfuran,apotentialglucosebasedbiofuel
Caramelization
Fludeoxyglucose(18F)
Glucosetransporter(GLUT):GLUT1,GLUT2
Glycatedhemoglobin
Peritonealdialysis
Sugarsinwine
Trinderglucoseactivitytest
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References
1.BoerioGoates,Juliana(1991),"Heatcapacitymeasurementsand
thermodynamicfunctionsofcrystallineDglucoseattemperaturesfrom10K
to340K",J.Chem.Thermodynam.23(5):4039,doi:10.1016/S0021
9614(05)801284.
2.Ponomarev,V.V.Migarskaya,L.B.(1960),"Heatsofcombustionofsome
aminoacids",Russ.J.Phys.Chem.(Engl.Transl.)34:118283.
3.Thnard,GayLussac,Biot,andDumas(1838)"RapportsurunmmoiredeM.
Pligiot,intitul:Recherchessurlanatureetlespropritschimiquesdessucres"
(http://gallica.bnf.fr/ark:/12148/bpt6k29662/f106.langEN)(Reportonamemoir
ofMr.Pligiot,titled:Investigationsonthenatureandchemicalpropertiesof
sugars),Comptesrendus,7:106113.Frompage109(http://gallica.bnf.fr/a
rk:/12148/bpt6k29662/f109.langEN):"IlrsultedescomparaisonsfaitesparM.
Pligot,quelesucrederaisin,celuid'amidon,celuidediabtesetceluidemiel
ontparfaitementlammecompositionetlesmmesproprits,etconstituentun
seulcorpsquenousproposonsd'appelerGlucose(1).(1),mot,vin
doux."ItfollowsfromthecomparisonsmadebyMr.Pligot,thatthesugar
fromgrapes,thatfromstarch,thatfromdiabetesandthatfromhoneyhave
exactlythesamecompositionandthesameproperties,andconstituteasingle
substancethatweproposetocallglucose(1)(1),must,sweetwine.
4."glucose."TheColumbiaEncyclopedia,6thed..2015.Encyclopedia.com.17
Nov.2015<http://www.encyclopedia.com>.
5.Bunn,H.F.Higgins,P.J.(1981)."Reactionofmonosaccharideswithproteins:
possibleevolutionarysignificance".Science213:222224.
doi:10.1126/science.12192669.
6.HighBloodGlucoseandDiabetesComplications:Thebuildupofmolecules
knownasAGEsmaybethekeylink,AmericanDiabetesAssociation,2010,
ISSN00958301
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Externallinks
GlucoseMSSpectrum(http://gmd.mpimpgolm.mpg.de/Spectrums/8dee81a18d984a73b55d9de42f10e190.aspx)
InternationalChemicalSafetyCard0865(http://www.inchem.org/documents/icsc/icsc/eics0865.htm)

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