ch_14_cyclic structures of monosaccharides
TRANSCRIPT
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Chapter 14.3
Cyclic Structures of Monosaccharides
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Monosaccharides in Nature
The linear form of monosaccharides isinstable - only 1%
C5 and C6 carbs form Hemiacetal or cyclicalform, ringform – 99%Sugars open and close randomly, fre uently
!ntermolecular rearrangement
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HemiacetalsGlucose: "ydro#yl group connects$ C5 → C1 forming a
1,5 ether lin a!e.Not a dehydration "ut a rearran!ement###
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cycli ation of glucoseCycli ation of glucose &
"ay'orth pro(ection
http://www.bing.com/videos/search?q=glucose%20ring%20closure%20animation&qs=n&form=QBVR&pq=glucose%20ring%20closure%20animation&sc=0-20&sp=-1&sk=http://www.bing.com/videos/search?q=cyclization%20of%20glucose&qs=n&form=QBVR&pq=cyclization%20of%20glucose&sc=3-22&sp=-1&sk=http://www.bing.com/videos/search?q=cyclization+of+glucose&FORM=HDRSC3&adlt=stricthttp://www.bing.com/videos/search?q=cyclization+of+glucose&FORM=HDRSC3&adlt=stricthttp://www.bing.com/videos/search?q=cyclization%20of%20glucose&qs=n&form=QBVR&pq=cyclization%20of%20glucose&sc=3-22&sp=-1&sk=http://www.bing.com/videos/search?q=glucose%20ring%20closure%20animation&qs=n&form=QBVR&pq=glucose%20ring%20closure%20animation&sc=0-20&sp=-1&sk=
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Hay$orth Structure of Glucose
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C1 :non%chiral in linear form"ut chiral in rin!: la"eled & or '
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Num"erin! Car"ons onHemiacetals
)l'ays start on the right hand side
1,5 *ther +in age
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Cyclic Structure of Galactose
alactose is an aldohe#ose that differs fromglucose only 'ith the –." group on carbon /
0ith formation of a ne' hydro#yl group oncarbon 1 – galactose also e#ists in 2 3 forms
4- alactose α- alactose β- alactose
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Cyclic Structure of (ructose
ructose is a etohe#ose$ C5 reacts 'ithetone group C
Smaller ring$ pentagon
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(ructose )in! num"erin!
,5-ether lin age
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Chapter 14.5
*isaccharides
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Glycosidic "ond formation
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Namin! of Glycosidic /onds:Maltose
Carbon @ of first sugar connected to Carbon@number of second sugar
7altose$ C1 is connected to C/C1 is also in & position
0riting con;entions$
81,/: glycosidic bondor alpha 81-/: A
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More e amples
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0ther !lycosidic "onds
"eta -1%4 !lycosidic "ond
http://www.google.com/imgres?q=glycosidic+bond+formation+of+carbohydrates&um=1&hl=en&safe=active&sa=N&tbo=d&biw=1280&bih=571&tbm=isch&tbnid=YAY-l7mvU_O1zM:&imgrefurl=http://en.wikibooks.org/wiki/Structural_Biochemistry/Carbohydrates/Disaccharides&docid=efGZxhIc6dYa_M&imgurl=http://upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Chitobiose.svg/361px-Chitobiose.svg.png&w=361&h=234&ei=NAQIUcfMEunQigKH3oDACw&zoom=1&iact=hc&vpx=146&vpy=102&dur=6986&hovh=181&hovw=279&tx=151&ty=82&sig=112028049467032634653&page=1&tbnh=141&tbnw=217&start=0&ndsp=18&ved=1t:429,r:1,s:0,i:86
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3 *isaccharides you need tono$1? 7altose – malt sugar
? +actose – mil sugar B?
Sucrose - table sugar
enerally, a disaccharide ischaracteri ed by>?1? 7onosaccharide components
? glycosidic bonds
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Maltose
7onomers$ 1? -4- lucose ? or 3-4- lucoselycosidic bond$ 81-/:
Creating t'o chiral ;ersions of 7altose 3 7altose 7altose
' -4-7altose &-4-7altose
3 of maltose is determined by the C1 position of
second sugar
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hat2s Maltose Malt Su!ar
.btained from thehydrolysis of starch
Dsed in cereals,candies, and bre'ingof be;erages
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+actose
7onomers$ 3-4-galactose 'ith - 3-4-glucose
lycosidic bond$ 3 81-/:Creating t'o chiral ;ersions of +actose
' -4-+actose &-4 -+actose
http://www.google.com/imgres?q=lactose+structure&hl=en&safe=active&tbo=d&biw=1280&bih=571&tbm=isch&tbnid=v6KlBn2AL-BJxM:&imgrefurl=http://users.bergen.org/dondew/bio/AnP/Anp1/AnP1Tri1/CARB_ART/LACTOSE_SYNTH/LactoseSynth.html&docid=GIpj14H8eeKCQM&imgurl=http://users.bergen.org/dondew/bio/AnP/Anp1/AnP1Tri1/CARB_ART/LACTOSE_SYNTH/Fig2lactose.gif&w=304&h=161&ei=nx4IUbbHIcjmigKwjoGoCQ&zoom=1&iact=hc&vpx=827&vpy=325&dur=2391&hovh=128&hovw=243&tx=129&ty=82&sig=112028049467032634653&page=1&tbnh=128&tbnw=243&start=0&ndsp=18&ved=1t:429,r:16,s:0,i:128
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+actose
7a es up 6-E% of human mil and
/-5% of co'Fs mil+actose intolerance$ lac of the en ymelact ase that splits disaccharide duringdigestion
dult Mammals stop e#pressing the lactasegene – e#ception$ many adult humans ha;ede;eloped a lactose tolerance
8microe;olution: but depends on ethnicity
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Sucrose
7onomers$ -4-glucose and 3-4-fructoselycosidic bond$ ,3 81, :
Creating only one formof 4-Sucrose
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Sucrose
Commercial sugar, obtained from sugarbeets and sugar cane
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Chapter 14.
6olysaccharides
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6olysaccharides
) polymer of many monosaccharides (oinedtogether$ glycosidic bd!mportant polysaccharides$1. mylose7 mylopectin –plant starch8. Glyco!en – animal starch3. Cellulose – plant fibers
7onomers$ all *%!lucose but differentglycosidic bonds
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mylose7 mylopectin
Common name starchesglucose storage in plant seeds, tubers etc
ound in grains, potatoes, beans, fruitsSoluble in 'ater Commercial Starch$ mi#ture amylose G%
and amylopectin EG%
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mylose
7onomer$ &%*%!lucose 8about GG-/GGG:lycosidic bond$ &%1,4%G/
*n yme brea ing it$ mylaseStructure$ +ong helical chain
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mylopectin
7onomer$ &, *%Glucoselycosidic &ond$ & -1,4 and & -1, &8e;ery 5 glucose monomers:
*n yme brea ing it$ amylase iso9ymesA/ranched starch H
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Glyco!en
)nimal starchStorage of glucose in the li;erSimilar to amylopectin only more branches8e;ery 1G-15 glucose molecules:
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Cellulose
7onomers$ ',*%!lucoselycosidic bond$ '1,4%!lycosidic "onds
*n yme brea ing it$ Cellulase
!nsoluble in 'ater straight strands, found in the cell 'all ofplants, ma e plant stal s rigid and strong
"umans, animal, plants *0 N0 H ;< theen yme cellulaseonly bacteria li;ing in the guts of ruminants
ha;e cellulase
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*i!estion of Cellulose
ra ing animals and termites harbor e-coli'ho digest cellulose for them
!n humans cellulose helps absorb to#ins fromdigestion of proteins to maintain a healthydigesti;e system
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Car"ohydrates in 0ur *iet
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Hydrolysis
Chemical reaction to separate polymers byinserting a 'ater molecule