Đ I CƯƠNG CARBOHYDRATE - WWW - Docsachysinh

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I CNG CARBOHYDRATE
Phng Trung Hng - Phan Nguyn Hu Trng - Nguyn Phc Long
Carbohydrate ng vai tr quan trng trong ha hc hu c k t khi khm ph ca Emil Fischer (1884-1891). Tn gi Carbohydrate xut pht t hp cht cha C, H, O vi t l H : O lun l 2:1 ( ging nh H2O). Cch gi ny khng ng nhng vn dc hiu l nc khng tn ti trong carbohydrate. Ngy nay thng gi l dn xut polyhydroxyaldehyde hay polyhydroxycetone. Ngoi ra cn c gi l glucide hay ng saccharide. T saccharide bt ngun t ting Hy Lp sakkarism ngha l ng n. Carbohydrate l nhm phn t sinh hc c mt nhiu nht trn tri t. Hng nm thc vt v to c kh nng bin i hn 100 t m3 CO2 v H2O thnh glucose v sn phm hu c khc. Mt s carbohydrate nh ng, tinh bt l thc n ch yu ca con ngi. Qu trnh oxy ha carbohydrate l ngun cung cp nng lng ch yu t bo d dng. Monosaccharide l ng n tng ng vi mt n v
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polyhydroxyaldehyde hoc cetone, ph bin nht l D- glucose. Oligosaccharide l mt chui cha mt s ( thng l 2,3,4 ) n v monosaccharide ni vi nhau thng qua lin kt glucoside, ph bin nht l ng i disaccharide D-glucose ni vi D-fructose bng lin kt cng ha tr. Nhng oligosaccharide cha nhiu hn 3 n v monosaccharide hu nh t gp trong t nhin trng thi t do. Polysaccharide l chui di cha hng trm, hng nghn n v ng n, trong c mt s dng si di nh cellulose v mt s khc dng phn nhnh rt mnh nh glucogen. Hai dng polysaccharide ph bin nht trong t nhin l Cellulose v tinh bt u c to t D-glucose nhng c lin kt khc nhau. Trong thc vt, glucide va l vt liu d tr va tham gia vo thnh phn ca m nng . i vi con ngi v ng vt, glucide l cht dinh dng gip cho c th tin hnh cc chc nng khc nhau v tham gia vo vic bo v c th khi b nhim trng, tham gia vo qu trnh phc hi v iu ha phn ng enzymee. Khi nim Carbohydrate cn gi l glucide c cng thc chung Cm(H2O)2n l mt trong nhng thnh phn c bn ca t bo v m trong c th sinh vt, ch yu l thc vt. Thc vt : chim khong 75% trong cc b phn nh c, qu, l, thn, cnh. ng vt : chim khong 2% trong gan, c mu Ngun gc glucide trong t nhin: c hnh thnh t trong l cy ca thc vt nh qu trnh quang hp ca nh sng mt tri v sc t
xanh chlorophyll ( dip lc ). 6CO2 + 6H2O asmt, cholorophyll nC6H12O6 xCO2 + yH2O Phn loi Carbohydrate c th c chia lm 3 nhm : 1.Monosaccharide : 1.1 Khi nim v phn loi : Monosaccharide u tin c tm thy l glucose vi cu trc 5 nhm hydroxyl, bi Alexander Kolli (1869). Monosaccharide cn gi l ng n v chng l thnh phn n gin nht ca carbohydrate v khng b thy phn. Monosaccharide c xem l sn phm oxy ha khng hon ton ca cc polyalcol, cng thc c cha chc aldehyde v cetone. Thng thng biu din mt phn t monosaccharide ngi ta s dng hnh chiu Fisher trong sn carbon nm trn trc thng ng nhm carbonyl nm v tr cao nht(3). Trong cng thc carbohydrate tn ti carbon bt i xng mang bn nhm th khc nhau. V th tn ti hai dng cng thc vi mi dng quay mt phng nh sng phn cc theo cc gc khc nhau. biu din cng thc khc nhau danh php D v L c s dng cng vi (+) v (-) ch chiu quay.
C6H12O6 + O2 (C6H10O5)n + nH2O Cx(H2O)y + xO2
Monosaccharide gi l D hay L ty theo cu hnh ca carbon phi i xng v tr thp nht trn trc thng ng ca hnh chiu Fisher, cn gi l nguyn t carbon tham chiu. Nu nhm OH gn vi carbon tham chiu nm bn phi th gi l D. Nu nhm OH gn vi carbon tham chiu nm bn tri th gi l L.
Cch gi tn cc hp cht monosaccharide :

-
Trong cng thc mang nhm aldydehyde th gi l :
Aldose Trong cng thc mang nhm cetone th gi l : Cetose
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Cng thc ca glucose c xc lp vo gia th k 19 da vo cc cng trnh nghin cu ca cc nh ha hc nh Dumas, Berthelot, Fittig, Bayer v Tollens. Tnh trin quang ca glucose v mt s ng khc cng c tha nhn trong khong thi gian , nhng cu trc phn t ch c bit n khi Vant Hoff v LeBel cng b l thuyt v nguyn t carbon phi i xng vo nm 1874. tng c rt nhiu nghin cu cho rng glucose c cu trc mch thng nhng cu trc ny khng gii thch c mt s tnh cht ha hc ca glucose: - Glucose ch cho mt s nhng khng phi tt c cc phn ng c trng ca aldehyde mch thng. - Phn ng ca glucose vi 1 mol methanol trong mi trng acid cho hai ng phn acetal.
- Kt tinh glucose t dung dch nc cho hai dng glucose vi nng sut quay cc khc nhau ([]D +112 v =18,7o) c hai dng glucose ny u c nng sut quay cc thay i v dng li cng mt v tr []D +52,7. Qu trnh ny gi l a trin ha. Tt c quan st trn u c gii thch nu cho rng glucose tn ti dng vng hemiacetal, to thnh t phn ng tr ha ni phn t ca mt nhm hydroxy vo nhm aldehyde. Ngy nay ngi ta bit rng glucose tn ti ch yu di dng hemiacetal vng 6 vi hai ng phn xuyn lp th ch khc nhau cu hnh ca nguyn t carbon hemiacetal phi i xng, cn c gi l carbon anomer.
S c mt ca nhm C=O v nhm OH trong cng mt phn t to iu kin cho s hnh thnh hemicetal vng. Bn cht ca vng ph thuc vo v tr ca nhm OH tham gia ng vng. S ng vng vi nhm OH C4 s cho vng furane c 5 cnh; vi nhm OH C5 s cho vng pyrane c 6 cnh. S chuyn i mt proton t nhm OH cho O ca nhm C=O lm xut hin mt nguyn t carbon bt i xng mi. V tr ca nhm OH trn nguyn t carbon ny quyt nh
dng hay .
Cc phn t thng c cu trc vng 5 hay vng 6, tng t nh hp cht d vng c cha oxy tng ng. Vng 5 gi l Furanose ging furan v vng 6 gi l pyranose nh pyran. Glucose ch yu tn ti dng pyranose.
Trong cng thc vng ( Fischer ) nhm OH bn acetal bn phi vng ( cng pha vi vng ) gi l a- ( cng thc I ), nhm OH bn tri vng ( khc pha vi vng gi l b - ( cng thc II ). a- v b - l 2 ng phn anomer vi nhau.
1.2.Cng thc Harworth v cng thc phi cnh: Cng thc Fisher biu din cu trc mch thng ca monosaccharide nhng cha gii thch c chiu di ni, c bit l khng th hin c s tng quan gia cc ng phn. Walter Harworth a ra cng thc phi cnh dng vng v phng ca phn t. Phn ca phn t gn ngi quan st c v m. Carbon anomer tn cng v bn phi v vng c nh s theo chiu kim ng h bt u t nguyn t carbon ny. Cc nhm th c gn trn cc lin kt thng ng t ti mi nguyn t carbon.
Trn cng thc chiu Fischer nhm OH bn acetal pha bn phi so vi mch thng ng ca carbon. Trn cng thc chiu Haworth nhm OH bn acetal pha di ca
vng. Nhm OH bn acetal bn tri so vi mch thng ng ca carbon th trn cng thc chiu Haworth phi trn ca vng. C th chuyn cng thc ca glucose t cng thc chiu Fisher thnh cng thc Harworth nh sau : Sa i cng thc chiu Fisher sao cho tt c cc nguyn t trn vng u nm trn mt ng thng. Xp cc nhm th bn tri cng thc chiu Fisher ln pha trn mt phng hnh lc gic v cc nhm bn phi v pha di mt phng hnh lc gic.
Mi quan h lp th c th hiu c hon chnh hn bng cng thc phi cnh dng gh. Nhng quy c dng v cng thc Harworth c th c p dng cho cng thc phi cnh. Cc nhm th bn tri ca cng thc Fisher c v pha bn kia ca vng theo quy c trc v xch o.
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Cng thc phi cnh glucose:
- Trong cng thc phi cnh v cng thc Harworth th ng phn D th nhm anomer hng xung di , cn ng phn L th nhm anomer hng ln trn. 1.3.Tnh cht ca monosaccharide : 1.3.1.Tnh ha tan: Trong phn t monosaccharide c mang nhiu nhm hydroxy phn cc mnh c kh nng to lin kt hydrogen, do quyt nh tnh ha tan v trng thi tp hp ca monosaccharide. a s monosaccharide l nhng cht khng bay hi, d ha tan trong nc, trong dimetylformamide, dimetylsulfoxide, ha tan c hn trong alcol, pyridine, acetic acid v khng ha tan trong dung mi hu c thng thng. Cc dn xut monosaccharide m cc nhm hydroxy b thay th d bay hi v c th chng ct. Trong dung dch cc monosaccharide b solvat ha mnh do tng tc
lng cc v to lin kt hydrogen vi dung mi nn dung dch monose c nht kh cao. trng thi vic nh hng cc phn t kh khn hn nn vic to thnh cc mm tinh th v qu trnh kt tinh b chm. Mt kh khn na l do cc dng h bin ca monosaccharide lm gim nng dng c kh nng kt tinh, nn kt tinh monosaccharide phi c mt s phng php c bit. C th da vo ha tan khc nhau ca cc v m ta c th c lp ring tng ng phn. V d : -D-Glucose km tan trong nc hn -D-Glucose, c th c lp tng ng phn. 1.3.2. Hin tng bi quay(4) : Tinh th -D-(+)-glucose c nhit nng chy 146oC. Khi ha tan vo nc c dung dch c quay cc +112o. Mt thi gian sau quay cc gim dn v t n gi tr khng i +52,7o. Mc khc tinh th -D-(+)-glucose kt tinh nhit 98oC c nhit nng chy 150oC, khi ho tan vo nc c dung dch c quay cc 19o v dn dn tng ln n gi tr khng i +52,7o. - Gii thch hin tng bi quay :
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S thay i gc quay cc t n gi tr cn bng ca mi loi ng phn ny gi l s bi quay. Tt c cc monosaccharide u c hin tng bi quay. Hin tng bi quay l nguyn nhn to ra cc ng phn anomer trong cc monosaccharide. 1.3.3. Tnh cht ha hc: a. Phn ng oxy ha : Cc monosaccharide d dng cho phn ng oxy ha, ph thuc vo cc iu kin khc nhau s to ra nhiu phn ng khc nhau. ng kh l nhng loi ng c th b oxy ha bng cc tc nhn oxy ha m du nh bendict, fehling Cu(OH)2 , tollens Ag(NH3)2NO3...
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S i mu trong qu trnh phn ng c th c quan st bng mt thng. Cc phn ng ny thng c dng nh lng ng trong mu v nc tiu. Ngoi ra mt s cht c th oxy ha cho ra diacid :
Acid periodic tc dng vi monosaccharide mch carbon b ct t v to dialdehyde.
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b.Phn ng kh : Kh nhm carbonyl ca monosaccharide bng hn hng natri trong H2SO4 long, natrihydride Bo ( NaBH4 ) hoc bng H2 c xc tc th to thnh cc polyalcol no. Polyalcol to thnh c tn gi nh monosaccharide tng ng nhng thay tip v ng ose bng it hoc itol.
c.Phn ng epimer ha: Cc monosaccharide c cng cng thc phn t c cu hnh ca cng mt carbon bt i xng (k t chc aldehyde) hon ton khc nhau th gi l ng phn epimer. V d : glucose, mannose, fructose l ng phn epimer vi nhau.
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Trong mi trng kim long hoc pyridin, mi monosaccharide nh D-glucose, D-Mannose, D-Fructose b epimer ha v to thnh hn hp 3 epimer. S epimer ha xy ra nh sau :
S epimer ha cng c kh nng xy ra trong iu kin khi monosacchairde tip xc vi dung dch brom, pyridin v tip theo l qu trnh kh ha.
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d. Phn ng to osazone : Monosaccharide tc dng vi 3 mol phenylhydrazin to phn t osazone :
Cc ng phn epimer u cho cng loi osazone. Osazone kt tinh c hnh th xc nh dng nhn bit cc monosaccharide. Cc ng phn epimer ca aldose v cetose c cu hnh C3, C4, C5 ging nhau chng c cng 1 osazone v khi to osazone khng cn carbon bt i xng ti C2. Bng ph hng ngoi cho thy phn t osazon bn v tn ti h lin hp v c lin kt hydro ni phn t ( C-OH-N).
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e. Phn ng to glycoside : Alcol hoc phenol tc dng vi nhm OH bn acetal ca monosaccharide to thnh hp cht alkyl (hoc aryl) glycoside.
Glycoside to thnh t glucose th gi l glucoside, t mannose th gi l mannoside, t galactose gi l galactoside, t fructose gi l fructoside. Cc glycosidee bn vng trong mi trng kim nhng rt d phn ly thnh monosaccharide v alcol trong mi trng acid v di tc
dng ca enzyme.
Lin kt glycosidee cn c to thnh gia cc phn t monosacharide vi nhau cho ra oligosaccharide (di, tri, tetraose) v polysaccharide. Cc glycosidee khng c hin tng bi quay v khng tc dng vi thuc th Fehling v thuc th Tollens. f. Phn ng to ether : Glucoside tc dng vi dimethylsulat trong mi trng kim to thnh methyl tetra o-methyl glucoside.
Hp cht methyl b -2,3,4,6-tetra-O-methyl-D-glucoside tc dng vi H2O trong mi trng acid th ch c lin kt oside O-CH3 ti nguyn t carbon s 1 b thy phn. Cc nhm O-CH3 khc hon ton khng b thy phn ( v chng l lin kt ether ).
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g. Phn ng to ester : Aldohexose b acetyl ha ( to ester ) bi anhydride acetic to hp cht acetylpyranose. V d : b -D-Glucose tc dng vi anhydride acetic to hp cht b -Dpentaacetylglucose.
Khi cho b -D-pentaacetylglucose tc dng HBr trong mi trng acide acetic th ch c chc ester ti carbon s 1 tham gia phn ng.
h. Phn ng to phc mu xanh vi Cu(OH)2 : Cc 3,4-diol ca 2 monosaccharide c th quay ngc chiu nhau
to phc ng :
i. Phn ng tng mch carbon : Khi cho cc aldose tc dng vi HCN thy phn, to lacton v sau kh ha th mch carbon ca aldose c tng ln. V d : t aldopentose s to thnh aldohexose.
k. Phn ng gim mch carbon : C th gim mch carbon ca aldose theo cc bc sau : - Oxy ha aldose bng dung dch brom. - Chuyn ha thnh mui calci. Oxy ha mui calci bng H 2O2 vi s c mt ca mui st Fe3+, aldose to thnh c s carbon gim i mt nguyn t.
Cc phn ng to glycoside, to ether, ester, tng, gim mch carbon l nhng phn ng quan trng xc nh cu to ca monosaccharide. l. Phn ng ln men : Ln men l qu trnh sinh ha rt phc tp xy ra do enzyme tc dng ln c cht, ngoi sn phm chnh cn c sn phm ph :
2.Oligosaccharide : 2.1.Khi nim v phn loi : Oligosaccharide l hp cht trung gian gia monosaccharide v polysaccharide ( theo ting Hy lp Oligo c ngha l mt t). Phn t oligosaccharide v polysaccharide u do cc monosaccharide kt
hp vi nhau bng lin kt O-glycosidee do nhm hydroxyl hemiacetal ca mt gc vi mt hydroxyl bt k ca mt gc khc. Thng thng ngi ta gi oligosaccharide l nhng glucide cha t 2 n 10 gc monosaccharide. Ty theo s lng monosacharride m ngi ta gi disaccharide, trisaccharide, tetrasaccharide Hu ht cc oligosaccharide d kt tinh, d ha tan, c v ngt v c phn t lng xc nh. n gin nht l ng i ( Disaccharide ). 2.2.Disaccharide: Dissacharide do hai phn t monosaccharide to thnh theo kiu glycosidee, cc gc c th ging nhau hoc khc nhau. Disaccharide c cng thc phn t : C12H22O11. Thy phn disaccharide to ra 2 phn t monosaccharide.
2.2.1. Saccharose: Saccharose rt ph bin vi tn gi ng ma thng c dng lm v ngt cho cc mn n, c s dng hng ngy trong gia nh. c tm thy trong nhiu loi cy nh : c ci ng, chi cao lng, nha cy g thch v quen thuc nht l cy ma ng. Trong hm lng ng trong c ci ng t 10%-20% , cy ma ng t 14%-25% , c s dng trong cng nghip tinh ch ng. Phn t saccharose c to thnh do -D-Glucose v -D-Fructose kt hp bng lin kt 1,2 gia hai nhm hydroxy glycosidee. Cn c gi l : -D-Glucopyranosil --D-fructofuranose. Saccharose
khng cn nhm hydroxyl hemiacetal nn khng c tnh kh. Khi un nng vi acid, saccharose d dng b thy gii to thnh glucose v fructose. Qu trnh gi l s nghch o v hn hp glucose v fructose gi l ng nghch o c quay m cc ( quay cc ca glucose l 52o5 v ca fructose l -92o4 ) .
2.2.2. Maltose: Maltose c tm thy trong ht u hay ht thc ang ny mm. Thu c khi thy phn tinh bt bng enzymees trong mch nha, v vy thng gi l ng mch nha. Ngoi ra maltose cng c hnh thnh trong qu trnh tiu ha phn gii tinh bt trong c th ng vt. Trong thng mi thy phn tinh bt bng acid sn xut siro. Phn t Maltose c to thnh t hai phn t D-glucose trong carbon anomer ca monosaccharide ny ni vi carbon s 4 ca monosaccharide kia nn maltose cn c tn gi 4-O- -Dglucopyranosil-D-glucose. Maltose c tnh kh nhng yu hn glucose 2 ln.
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2.2.3.Lactose: Lactose cng c gi l ng sa v n c trong sa loi c v khong 4-5%. Trong thng mi lactose c s dng sn xut thc n cho tr em v c bit cho ngi n king. Phn t lactose do -D-galactose v -D-glucose kt hp vi nhau bng lin kt 1-4 nn lactose cn c tn 4-O- -D-galactopyranosylD-glucose. Phn t lactose cn mt nhm hydroxy glucoside nn cn c tnh kh.
3.Polysaccharide: Polysaccharide l nhng hp cht bao gm hng trm n hng nghn monosaccharide kt hp vi nhau bng lin kt glycoside. Polysaccharide mang nhiu tnh cht khc vi mono v disaccharide nh : khng c phn ng kh, khng c v ngt, thng khng tan
trong nc, khi ha tan d hnh thnh dung dch keo. Trong phn t disaccharide khi hai phn t kt hp s tch mt phn t nc. V th mt hexose polysaccharide c th biu din bng cng thc chung (C6H 10O5)x . x ch s phn t hexose trong polysaccharide. Do phc tp ca polysaccharide nn s lng phn t glucose trong cng thc vn ch mang tnh c lng. Phn t polysaccharide c th gm mt hoc vi loi monome khc nhau, do ngi ta chia ra polysaccharide ng th v polysaccharide d th. Do h thng phc tp nn hu nh cha c tn gi dnh ring cho polysaccharide. Thng thng gi tn mt polysacharide ngi ta thay vn ose trong monosaccharide tng ng bng vn an. V d : D-Glucan l polyme ch do D-glucose to nn. D-Galacto-manoglucan l polyme c cha gc D-galactose v D-mannose. Ty theo ngun gc ngi ta phn cc polysaccharide t nhin ra ba nhm ln : Phytopolysaccharide ( polysaccharide thc vt ) Zoopolysaccharide ( polysaccharide ng vt ) Polysaccharide vi sinh vt. Glycogen : L glycogen d tr v cng l ngun cung cp nng lng chnh ca ngi v ng vt, ngoi ra cn c ng gp mt phn nh vo p sut thm thu trong bo tng. C cu to gn ging vi amylopectin nhng phn t glycogen c mch phn nhnh nhiu hn v c s n v glucose ( 12-18 n v glucose ) t hn amylopectin. Trong cng thc cu to, n c c lin kt (1,4) v nhnh(1,6).
M phng lin kt 1,4 v 1,6Glycosidic

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Ngy 3 thng 3 nm 2014

I CNG CARBOHYDRATE - www.docsachysinh.com

c sch Y sinh || www.docsachysinh.com || Microworld Macromind

Ngy 3 thng 3 nm 2014

I CNG CARBOHYDRATE - www.docsachysinh.com

Ngy 3 thng 3 nm 2014

I CNG CARBOHYDRATE - www.docsachysinh.com

C6H12O6 + O2 (C6H10O5)n + nH2O Cx(H2O)y + xO2

Ngy 3 thng 3 nm 2014

I CNG CARBOHYDRATE - www.docsachysinh.com

Cch gi tn cc hp cht monosaccharide :

Trong cng thc mang nhm aldydehyde th gi l :

Aldose Trong cng thc mang nhm cetone th gi l : Cetose

Ngy 3 thng 3 nm 2014

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Ngy 3 thng 3 nm 2014

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Ngy 3 thng 3 nm 2014

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Ngy 3 thng 3 nm 2014

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Ngy 3 thng 3 nm 2014

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Ngy 3 thng 3 nm 2014

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Cng thc phi cnh glucose:

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Ngy 3 thng 3 nm 2014

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Acid periodic tc dng vi monosaccharide mch carbon b ct t v to dialdehyde.

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d. Phn ng to osazone : Monosaccharide tc dng vi 3 mol phenylhydrazin to phn t osazone :

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Ngy 3 thng 3 nm 2014

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M phng lin kt 1,4 v 1,6Glycosidic

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