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BiotinWikipedia

Biotin
FromWikipedia,thefreeencyclopedia

BiotinisawatersolubleBvitamin,alsocalledvitaminB7

Biotin[1]

andformerlyknownasvitaminHorcoenzymeR.[2]
Itiscomposedofaureidoringfusedwitha
tetrahydrothiophenering.Avalericacidsubstituentis
attachedtooneofthecarbonatomsofthe
tetrahydrothiophenering.Biotinisacoenzymefor
carboxylaseenzymes,involvedinthesynthesisoffatty
acids,isoleucine,andvaline,andingluconeogenesis.
Biotindeficiencycanbecausedbyinadequatedietaryintake
orinheritanceofoneormoreinborngeneticdisordersthat
affectbiotinmetabolism.Subclinicaldeficiencycancause
mildsymptoms,suchashairthinningorskinrashtypically
ontheface.Neonatalscreeningforbiotinidasedeficiency
beganintheUnitedStatesin1984andtodaymanycountries
testforthisdisorderatbirth.Individualsbornpriorto1984
areunlikelytohavebeenscreened,thusthetrueprevalence
ofthedisorderisunknown.

Contents
1
2
3
4
5
6
7

General
Biosynthesis
Cofactorbiochemistry
DietaryReferenceIntake
Sources
Importintothecell
Bioavailability
7.1 Factorsthataffectbiotinrequirements
8 Deficiency
9 Metabolicdisorders
10 Useinbiotechnology
11 Toxicity
12 Seealso
13 References
14 Externallinks

Names
IUPACname
5[(3aS,4S,6aR)2oxohexahydro1Hthieno[3,4
d]imidazol4yl]pentanoicacid
Othernames
VitaminB7VitaminHCoenzymeR
Biopeiderm
Identifiers
CASNumber

px?ref=58855)
3Dmodel(Jmol)

Interactiveimage(http://chema
pps.stolaf.edu/jmol/jmol.php?m
odel=O%3DC1N%5BC%40%4
0H%5D2%5BC%40%40H%5
D%28SC%5BC%40%40H%5D
2N1%29CCCCC%28%3DO%2
9O)
Interactiveimage(http://chema
pps.stolaf.edu/jmol/jmol.php?m
odel=C1%5BC%40H%5D2%5
BC%40%40H%5D%28%5B
C%40%40H%5D%28S1%29C
CCCC%28%3DO%29O%29N
C%28%3DO%29N2)

ChEBI

CHEBI:15956(https://www.eb
i.ac.uk/chebi/searchId.do?chebi

General
Biotinisnecessaryforcellgrowth,theproductionoffatty
acids,andthemetabolismoffatsandaminoacids.[2]Biotin
assistsinvariousmetabolicreactionsinvolvingthetransfer
ofcarbondioxide.Itmayalsobehelpfulinmaintaininga
steadybloodsugarlevel.Biotinisoftenrecommendedasa
dietarysupplementforstrengtheninghairandnails,though

Id=15956)
ChEMBL

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

58855(http://www.commonc
hemistry.org/ChemicalDetail.as

ChEMBL857(https://www.ebi.
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scientificdatasupportingthisoutcomeareweak.[2]
Nevertheless,biotinisfoundinmanycosmeticsandhealth
productsforthehairandskin.[3][4]
Biotindeficiencyisrare.Theamountsneededaresmall,a
widerangeoffoodscontainbiotin,andintestinalbacteria
synthesizebiotin,whichisthenabsorbedbythehostanimal.
Forthatreason,statutoryagenciesinmanycountries,for
exampletheUSA[5]andAustralia,[6]havenotformally
establishedarecommendeddailyintakeofbiotin.Instead,an
AdequateIntake(AI)isidentifiedbasedonthetheorythat
averageintakemeetsneeds.Futureresearchcouldresultin
biotinAIswithEARsandRDAs(seeDietaryReference
Intakesection).
Anumberofraremetabolicdisordersexistinwhichan
individual'smetabolismofbiotinisabnormal,suchas
deficiencyintheholocarboxylasesynthetaseenzymewhich
covalentlylinksbiotinontothecarboxylase,wherethebiotin
actsasacofactor.[7]

Biosynthesis
Biotinhasanunusualstructure(seeabovefigure),withtwo
ringsfusedtogetherviaoneoftheirsides.Thetworingsare
ureidoandthiophenemoieties.Biotinisaheterocyclic,S
containingmonocarboxylicacid.Itismadefromtwo
precursors,alanineandpimeloylCoAviathreeenzymes.8
Amino7oxopelargonicacidsynthaseisapyridoxal5'
phosphateenzyme.ThepimeloylCoA,couldbeproduced
byamodifiedfattyacidpathwayinvolvingamalonyl
thioesterasthestarter.7,8Diaminopelargonicacid(DAPA)
aminotransferaseisunusualinusingSadenosylmethionine
(SAM)astheNH2donor.Dethiobiotinsynthetasecatalyzes
theformationoftheureidoringviaaDAPAcarbamate
activatedwithATP.BiotinsynthasereductivelycleavesSAM
intoadeoxyadenosylradicalafirstradicalformedon
dethiobiotinistrappedbythesulfurdonor,whichwasfound
tobetheironsulfur(FeS)centercontainedintheenzyme.[8]

ac.uk/chembldb/index.php/com
pound/inspect/ChEMBL857)
ChemSpider

62.html)
DrugBank

DB00121(http://www.drugban
k.ca/drugs/DB00121)

ECHAInfoCard

100.000.363(https://echa.europ
a.eu/substanceinformation//su
bstanceinfo/100.000.363)

IUPHAR/BPS

4787(http://www.guidetophar
macology.org/GRAC/LigandDi
splayForward?tab=summary&li
gandId=4787)

KEGG

D00029(http://www.kegg.jp/en
try/D00029)

PubChem

171548(https://pubchem.ncbi.n
lm.nih.gov/compound/171548)

UNII

6SO6U10H04(http://fdasis.nl
m.nih.gov/srs/srsdirect.jsp?regn
o=6SO6U10H04)

InChI
SMILES

Properties
Chemicalformula

C10H16N2O3S

Molarmass

244.31gmol1

Appearance

Whitecrystallineneedles

Meltingpoint

232to233C(450to451F
505to506K)

Solubilityinwater

22mg/100mL
Pharmacology

ATCcode

Cofactorbiochemistry
D(+)Biotinisacofactorresponsibleforcarbondioxide

149962(http://www.chemspide
r.com/ChemicalStructure.1499

A11HA05(WHO(http://www.
whocc.no/atc_ddd_index/?code
=A11HA05))
Hazards

NFPA704

transferinseveralcarboxylaseenzymes:
AcetylCoAcarboxylasealpha
AcetylCoAcarboxylasebeta
MethylcrotonylCoAcarboxylase
PropionylCoAcarboxylase
Pyruvatecarboxylase

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

?)

Infoboxreferences

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Biotinisimportantinfattyacidsynthesis,branchedchainaminoacid
catabolism,andgluconeogenesis.[2]Itcovalentlyattachestotheepsilonamino
groupofspecificlysineresiduesinthesecarboxylases.Thisbiotinylation
reactionrequiresATPandiscatalyzedbyholocarboxylasesynthetase.[9]In
bacteria,biotinisattachedtobiotincarboxylcarrierprotein(BCCP)bybiotin
proteinligase(BirAinE.coli).[10]Theattachmentofbiotintovarious
chemicalsites,biotinylation,isusedasanimportantlaboratorytechniqueto
studyvariousprocesses,includingproteinlocalization,proteininteractions,
DNAtranscription,andreplication.Biotinidaseitselfisknowntobeableto
biotinylatehistoneproteins,[11]butlittlebiotinisfoundnaturallyattachedto
chromatin.
Biotinbindstightlytothetetramericproteinavidin(alsostreptavidinand
neutravidin),withadissociationconstantKdontheorderof1015M,whichis
oneofthestrongestknownproteinligandinteractions.[12]Thisisoftenusedin
differentbiotechnologicalapplications.Until2005,veryharshconditionswere
thoughttoberequiredtobreakthebiotinstreptavidinbond.[13]

DeanBurk,American
biochemistwhocodiscovered
biotin.

DietaryReferenceIntake
TheFoodandNutritionBoardoftheU.S.InstituteofMedicineupdatedEstimatedAverageRequirements
(EARs)andRecommendedDietaryAllowances(RDAs)forBvitaminsin1998.Atthattimetherewasnot
sufficientinformationtoestablishEARsandRDAsforbiotin.Ininstancessuchasthis,theBoardsets
AdequateIntakes(AIs),withtheunderstandingthatatsomelaterdate,AIswillbereplacedbymoreexact
information.ThecurrentAIforadultsages19andupis30g/day.AIforpregnancyis30g/day.AIfor
lactationis35g/day.Forinfantsupto12monthstheAIis56g/dayForchildrenages118yearstheAI
increaseswithagefrom8to25g/day.[14]
Asforsafety,theFNBsetsTolerableUpperIntakeLevels(knownasULs)forvitaminsandmineralswhen
evidenceissufficient.InthecaseofbiotinthereisnoUL,asthereisinsufficienthumandatatoidentifyadverse
effectsfromhighdoses.TheEuropeanFoodSafetyAuthorityreviewedthesamesafetyquestionandalso
reachedtheconclusionthattherewasnotsufficientevidencetosetaULforbiotin.[15]CollectivelytheEARs,
RDAs,AIsandULsarereferredtoasDietaryReferenceIntakes.
ForU.S.foodanddietarysupplementlabelingpurposestheamountinaservingisexpressedasapercentof
DailyValue(%DV).Forbiotinlabelingpurposes100%oftheDailyValuewas300g,butasofMay2016it
hasbeenrevisedto30gtobringitintoagreementwiththeAI.AtableoftheprechangeadultDailyValuesis
providedatReferenceDailyIntake.FoodandsupplementcompanieshaveuntilJuly2018tocomplywiththe
change.

Sources
Biotinisconsumedfromawiderangeoffoodsourcesinthediet,butfewareparticularlyrichsources.Foods
witharelativelyhighbiotincontentincludepeanuts,Swisschardandotherleafygreenvegetables,rawegg
yolk(however,theconsumptionofavidincontainingeggwhiteswitheggyolksminimizestheeffectivenessof
eggyolk'sbiotininone'sbody),liver,andSaskatoonberries.ThedietarybiotinintakeinWesternpopulations
hasbeenestimatedtobe35to70g/d(143287nmol/d).[16]
Biotinisalsoavailableinsupplementformandcanbefoundinmostpharmacies.Thesyntheticprocess
developedbyLeoSternbachandMosesWolfGoldberginthe1940susesfumaricacidasastartingmaterial.[17]

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Importintothecell
InmammalsbiotinisimportedintocellsbytheNa+dependentmultivitamin(pantothenate,biotin,lipoate)
transporter(SMVT).[18]
Inbacteria,severalfamiliesofproteins,especiallytheBioYfamilyoftransporters,importsbiotinintocells.[19]

Bioavailability
BiotinisalsocalledvitaminH(theHrepresentsHaarundHaut,Germanwordsfor"hairandskin")orvitamin
B7.Studiesonitsbioavailabilityhavebeenconductedinratsandinchicks.Basedonthesestudies,biotin
bioavailabilitymaybeloworvariable,dependingonthetypeoffoodbeingconsumed.Ingeneral,biotinexists
infoodasproteinboundformorbiocytin.[20]Proteolysisbyproteaseisrequiredpriortoabsorption.This
processassistsfreebiotinreleasefrombiocytinandproteinboundbiotin.Thebiotinpresentincornisreadily
availablehowever,mostgrainshaveabouta2040%bioavailabilityofbiotin.[21]
Thewidevariabilityinbiotinbioavailabilitymaybeduetotheabilityofanorganismtobreakvariousbiotin
proteinbondsfromfood.Whetheranorganismhasanenzymewiththatabilitywilldeterminethe
bioavailabilityofbiotinfromthefoodstuff.[21]

Factorsthataffectbiotinrequirements
Thefrequencyofmarginalbiotinstatusisnotknown,buttheincidenceoflowcirculatingbiotinlevelsin
alcoholicshasbeenfoundtobemuchgreaterthaninthegeneralpopulation.Also,relativelylowlevelsof
biotinhavebeenreportedintheurineorplasmaofpatientswhohavehadapartialgastrectomyorhaveother
causesofachlorhydria,burnpatients,epileptics,elderlyindividuals,andathletes.[21]Pregnancyandlactation
maybeassociatedwithanincreaseddemandforbiotin.Inpregnancy,thismaybeduetoapossibleacceleration
ofbiotincatabolism,whereas,inlactation,thehigherdemandhasyettobeelucidated.Recentstudieshave
shownmarginalbiotindeficiencycanbepresentinhumangestation,asevidencedbyincreasedurinary
excretionof3hydroxyisovalericacid,decreasedurinaryexcretionofbiotinandbisnorbiotin,anddecreased
plasmaconcentrationofbiotin.Additionally,smokingmayfurtheracceleratebiotincatabolisminwomen.[22]

Deficiency
Biotindeficiencytypicallyoccursfromdietaryabsenceofthevitamin.Consumingraweggwhitesovermonths
mayresultinbiotindeficiency.[2]
Deficiencycanbeaddressedwithnutritionalsupplementation.[2]
Deficiencysymptomsinclude:
Brittleandthinfingernails
Hairloss(alopecia)
Conjunctivitis
Dermatitisintheformofascaly,redrasharoundtheeyes,nose,mouth,andgenitalarea.
Neurologicalsymptomsinadults,suchasdepression,lethargy,hallucination,andnumbnessandtingling
oftheextremities[2]
Theneurologicalandpsychologicalsymptomscanoccurwithonlymilddeficiencies.Dermatitis,
conjunctivitis,andhairlosswillgenerallyoccuronlywhendeficiencybecomesmoresevere.[2]

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Individualswithhereditarydisordersofbiotindeficiencyhaveevidenceofimpairedimmunesystemfunction,
includingincreasedsusceptibilitytobacterialandfungalinfections.[23]
Pregnantwomentendtohaveahighriskofbiotindeficiency.Nearlyhalfofpregnantwomenhaveabnormal
increasesof3hydroxyisovalericacid,whichreflectsreducedstatusofbiotin.[23]Severalstudieshavereported
thispossiblebiotindeficiencyduringthepregnancymaycauseinfants'congenitalmalformations,suchascleft
palate.Micefedwithdriedraweggtoinducebiotindeficiencyduringthegestationresultedinupto100%
incidenceoftheinfants'malnourishment.Infantsandembryosaremoresensitivetothebiotindeficiency.
Therefore,evenamildlevelofthemother'sbiotindeficiencythatdoesnotreachtheappearanceof
physiologicaldeficiencysignsmaycauseaseriousconsequenceintheinfants.

Metabolicdisorders
Inheritedmetabolicdisorderscharacterizedbydeficientactivitiesofbiotindependentcarboxylasesaretermed
multiplecarboxylasedeficiency.Theseincludedeficienciesintheenzymesholocarboxylasesynthetaseor
biotinidase.Holocarboxylasesynthetasedeficiencypreventsthebody'scellsfromusingbiotineffectively,and
thusinterfereswithmultiplecarboxylasereactions.[24]Biochemicalandclinicalmanifestationsinclude:
ketolacticacidosis,organicaciduria,hyperammonemia,skinrash,feedingproblems,hypotonia,seizures,
developmentaldelay,alopecia,andcoma.
Biotinidasedeficiencyisnotduetoinadequatebiotin,butrathertoadeficiencyintheenzymesthatprocessit.
Biotinidasecatalyzesthecleavageofbiotinfrombiocytinandbiotinylpeptides(theproteolyticdegradation
productsofeachholocarboxylase)andtherebyrecyclesbiotin.Itisalsoimportantinfreeingbiotinfromdietary
proteinboundbiotin.[24]Generalsymptomsincludedecreasedappetiteandgrowth.Dermatologicsymptoms
includedermatitis,alopecia,andachromotrichia(absenceorlossofpigmentinthehair).[25]Perosis(a
shorteningandthickeningofbones)isseenintheskeleton.Fattyliverandkidneysyndromeandhepatic
steatosisalsocanoccur.[21]

Useinbiotechnology
Biotiniswidelyusedthroughoutthebiotechnologyindustrytoconjugateproteinsforbiochemicalassays.[26]
Biotin'ssmallsizemeansthebiologicalactivityoftheproteinwillmostlikelybeunaffected.Thisprocessis
calledbiotinylation.Becausebothstreptavidinandavidinbindbiotinwithhighaffinity(Kdof1014mol/lto
1015mol/l)andspecificity,biotinylatedproteinsofinterestcanbeisolatedfromasamplebyexploitingthis
highlystableinteraction.Thesampleisincubatedwithstreptavidin/avidinbeads,allowingcaptureofthe
biotinylatedproteinofinterest.Anyotherproteinsbindingtothebiotinylatedmoleculewillalsostaywiththe
beadandallotherunboundproteinscanbewashedaway.However,duetotheextremelystrongstreptavidin
biotininteraction,veryharshconditionsareneededtoelutethebiotinylatedproteinfromthebeads(typically
6MguanidineHClatpH1.5),whichoftenwilldenaturetheproteinofinterest.Tocircumventthisproblem,
beadsconjugatedtomonomericavidincanbeused,whichhasadecreasedbiotinbindingaffinityof
~108mol/l,allowingthebiotinylatedproteinofinteresttobeelutedwithexcessfreebiotin.
Asoneofthestrongestnoncovalentinteractions,thebindingofbiotintostreptavidiniscommonlyusedasthe
targetmolecularinteractionintheresearchofbiosensorsandcellsorting.[27][28]
ELISAsoftenmakeuseofbiotinylatedsecondaryantibodiesagainsttheantigenofinterest,followedbya
detectionstepusingstreptavidinconjugatedtoareportermolecule,suchashorseradishperoxidaseoralkaline
phosphatase.

Toxicity
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Animalstudieshaveindicatedfew,ifany,effectsduetohighleveldosesofbiotin.Thismayprovideevidence
thatbothanimalsandhumanscouldtoleratedosesofatleastanorderofmagnitudegreaterthaneachoftheir
nutritionalrequirements.Therearenoreportedcasesofadverseeffectsfromreceivinghighdosesofthe
vitamin,inparticular,whenusedinthetreatmentofmetabolicdisorderscausingsebhorrheicdermatitisin
infants.[29]However,excessbiotinaccumulationcaninhibitendogenoussirtuinactivityleadingtoincreased
inflammation,cellularity,andcollagendeposition,andmaybepartlyresponsibleforagerelatedmetabolic
problems.Reversedbycalorierestrictioninmice.[30]

Seealso
Biotinylation
Multiplecarboxylasedeficiency
NeutrAvidin
Photobiotin
Streptag
Streptavidin

References
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2."Biotin:MedlinePlusSupplements".13September
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5.Otten,JJHellwig,JPMeyers,LD.,eds.(2006).
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NutrientRequirements.TheNationalAcademies
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"Biotinylationofhistonesbyhumanserum
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12.LaitinenOH,HytnenVP,NordlundHR,Kulomaa
MS(2006)."Geneticallyengineeredavidinsand
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LundebergJ,UhlnM(2005)."Thebiotin
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