Acyclic to Cyclic Carbohydrates
Transcript of Acyclic to Cyclic Carbohydrates
AcyclictoCyclicCarbohydrates:AFocusonGlucose
Havingtroubleseeingcarbohydratesintheiracyclicandcyclicform?
Confusedattheconnectivityandconformation?
Well,you’vecometotherightplace.
We’llbelookingattheacyclicformofglucoseinparticular
andhowtheacyclicformconvertstothecyclic.
Togoaboutthistopic,thebestideaisprobablytofirstbuildamodel.Wewillbeginbybuildingthestructurebasedontheimagebelow.Whenlookingatthegeneralandcommonlyseenacyclicstructure,youmaynoticethatboththehydrogenatomsandthealcoholgroupsprojecttowardstheviewer.Thismayconfusesomepeoplewhoareusedtothepresenceofonewedgeandonegroupconnectedwithdashedlines.Italsomayappeardeceivingbecausetheimagepresentsthemoleculealmostasifitwereplanar.BuildthemodelsothatthecarbonylisatthetopandtheCH2OHgroupisclosesttothebottom.
Youcanseethat
thecarbonylgroupandtheCH2OHgroup
collideintooneanother
Thewedgesshowthatthehydrogen
atomsandthealcoholgroupspointtowardtheviewer.
Iffocusingonanindividualcarbon,let’ssaythefirstafterthecarbonyl,youwillseethatthecarbonsconnectedtoitwill
pointwayfromtheviewerasrepresentedwithdashedlinesandtheothergroupsconnectedwillpoint
towardstheviewer.Thiswillbeseeninthebuiltmodel.
Afterbuildingthemodel,youfindthattheconnectedcarbonatomsformaringshapedstructure,withtheCH2OHgroupandthecarbonylcollidingintooneanother.Besuretorotatetheatomssothatthehydrogenatomsandthealcoholgroupsofthecarbonstereocenterspointtowardtheviewer.Ifyouweretolookateachindividualcarbonthatisastereocenter(thecarbonsexcludingthoseinthecarbonylandintheCH2OHgroup)youcanseethatitfitstheimageabove.Thecarbonsconnectedtotheparticularcarbonthatyouchoosetofocusonpointawayfromtheviewerwhiletheotherconnectedpointtowardtheviewer.
Hereisanotherviewofthemoleculefromits
side.Fromthisangle,whichisadifferentanglethantheoriginalimagefromwhichwebuiltthemodelbasedoffof,wecanseea
clearerimageofthecollidingcarbonylandCH2OHgroup.Already,youcanstarttoseehowthecyclicformwilltakeplace.
Switchingtothisview,wewillnowconverttheacyclicformtothecyclicform.Twistthemoleculeas
neededsothatthecarbonylandCH2OHgroupnolongercollideinordertoseethemoleculemoreclearly.
Glucoseisapyranose,whichmeansitformsasix‐memberedring.Inthecaseofglucose,thecarbonof
thecarbonylwillbondwiththealcoholofthecarbonjustabovetheCH2OHgroupinordertomakeasixmemberedring.Rememberthatthoughglucosedoes
indeedcontainsixcarbons,itisnotexactlyasixcarbonring.Theringwillconsistoffivecarbonatomsandoneoxygenatom.Thesixthcarbonwillbeanequatorial
branchconnectedtothering.
Thisbondingwillnowbeshownthroughimagesofthemodelforclarity.Inthetwoimagesshownabove,thedoublebondfromtheoxygenofthecarbonylhasbeenremovedandreplacedwithayellow“stick”orbond.Thechoiceofadifferentcoloredstickisonlysothatitwillbeeasiertodistinguishandfindtheanomericcarbonandkeeptrackofitslocation.ThealcoholgroupofthecarbonnearesttotheCH2OHgrouphasalsobeenrotatedsothattheoxygenpointstowardtheanomericcarbon.Youmaynoticethatthealcoholhaslostitshydrogenatom.Donotworryaboutthisdetail,forwearefocusingonstructureratherthanreactivity.Youmayalsonoticethatastick,representativeofabond,hasbeenplacedonthegroundbetweentheanomericcarbonandtheoxygenatom.Thisiswherethejoiningwilltakeplacetoconverttheacyclicmoleculetothecyclicform.
TheoxygenofwhatwasthealcoholgroupofthecarbonabovetheCH2OHgrouphasnowbeenjoinedtoformabondwiththeanomericcarbon.
Thisisthetopviewofthecyclicmolecule.
Bytiltingthemolecule,youcanseethe
familiarchairconformationthatisoftendrawninChem14C.Noticethatallthealcoholgroupsareequatorial.Thisisaunique
characteristicofglucose.Theoxygenoftheanomericcarbonshouldbeanalcoholgroup,butthatchangeisnotshownhereandthe
hydrogenatomhasbeenomitted.
WorksCited
http://www.chem.ucla.edu/harding/index.html