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Carbohidratos

Introduccin
Monosacridos Oligosacridos Polisacridos

Carbohidratos
Celulosa
n

Pedro Antonio Garca Ruiz


Catedrtico de Escuela Universitaria Area Qumica analtica Profesor Titular de Universidad Area Qumica Orgnica

Departamento de Qumica Orgnica - Universidad de Murcia

Carbohidratos
Introduccin
Monosacridos Oligosacridos Polisacridos

Introduccin Que es un carbohidrato?


Son polihidroxi aldehdos o cetonas o compuestos que conducen a ellos por hidrlisis y sus derivados. Se denominan Hidratos de carbono por responder muchos de ellos a la formula emprica:

C (H2O)n

Introduccin Que es un carbohidrato?


Se producen en la fotosntesis. Las plantas verdes contienen clorofila que capta de la luz solar la energa necesaria para realizar el proceso:

6 CO2 H2O

C6(H2O)6 + 6

Introduccin Como se clasifican?


C a r b o h i d r a t o s

Monosacridos Azcares Oligosacridos

Aldosas Cetosas
-2 -3 -4 Di Tri tetr pent Hex Hept

Polisacridos

-5 -6 -7

Introduccin Para qu sirven?


-

Como principios inmediatos son soportes de la vida Alimento


Cultura Higiene Comodidad Furfural Conserva Celulosa Alcohol Medicina Decoracin Polesteres Farmacia Bebidas

- Proporcionan:

Casa Vestido

- Muchas aplicaciones en la industria Qumica

Polmeros Sintesis Quiral

Carbohidratos
Introduccin
Monosacridos Oligosacridos Polisacridos

Monosacridos Estructura Reacciones y derivados Aislamiento y anlisis

Monosacridos

Estructura
Aldosas Cetosas Estructura cclica

Monosacridos

Estructura

Aldosas
Tres carbonos: Aldotriosas
CHO CHO

OH

HO

CH2 OH

CH2 OH

D (+)
Gliceraldhido

L (-)

currentpoint

Monosacridos

Estructura

Aldosas
Cuatro carbonos: Aldotetrosas

6 nd 120 1 4370 1796 4552 1952 4352 4513 4214 2095 1822 3122 dL DSt 1 1952 [14 59 [12 1345 2047 2086 1878 1904 2736 2756 2580 2606 1033 50 I 3122 I 1345 2464 40 4370 1427 4921 1952 4352 4882 3845 2464 1453 3122 80 3425 1952 2580 40 1714] 2416] 2455] 1878] 1904] 3105] 3125] 2580] 2606] 3425] 20 DSt 1714] DSt chemdict gr [13 [0 II 1453 1952 begin 211 /bs[[1 [1 ]d 2606 gr 1 2 gs 2606 end 1714 120 4370 1796 4552 1952 4352 4513 4214 2095 1822 3122 SP dL DSt 1 1952 DSt DSt [14 54 [12 1345 2047 2086 1878 1904 2736 2756 2580 2606 1033 50 Db [1 I 3122 I 1345 2464 I 40 4370 1427 4921 1952 4352 4882 3845 2464 1453 3122 4370 80 3425 1952 2580 40 1714] 2416] 2455] 1878] 1904] 3105] 3125] 2580] 2606] 3425] 1714 20 DSt 1714] DSt DSt chemdict gr [13 [2 [0I II1952 1453 1952 begin 2416 2606 1714 SP DSt DSt DSt [3 D [

m2 W dv p 1 hemDraw opyRight {6 m A x dict/chemdict p}{sqrt grestore -9.6 r l A}{cw ransform cY OrA{py 2 lt{1 mv -2 m 180 sc px cm p s mv -1 2 0 gr}{pp}{gs exec}{al dv a}b/PT{8 dp sm s{dp dv m HA}{dL g mv dv rO x dp dv -.6 sc py WI neg 12 exec sm 0 -1 neg b2 np CA lp st wF p mv n LB 0 py 1.2 p 5 sc -9.6 bd neg p gr at mv a}{ex p st px e OA}{1 1 1986, e lL/gs/gsave arcn m l Laser gs p cp clip}b/Ct{bs L/xl/translate aL mv neg}if/py ln 0 p ex 5 2 gr np 2.25 pp st}b/HA{lW at OB l0 sl o wy 16.8 p 1 mv 1 -1 m px fill 0 gs n/ex py counttomark{bs 12 lp 145 90 3.375 ro 8 l ac st}{0 sg n aR 1987, 1 r np bW wx py Prep gr -1 SA ix 0.6 ac bd 0.3 dv px dp sc OB/bL ro cv 8 fill aL dict 1 rad end}b/Db{bs{dp x sc p at 0 DA}{dL n 0 neg DLB py dp m1 1.2 -9.6 x 1 L/ie/ifelse gr eq{DD}{DS}ie SA ey 0 l8 ne{bW py m Cambridge 120 p mt bd px dp sc 0 p put rot rO -1 cm m l}for n/ey m/w L/S{sf DA}{cw x p m 180 e 2 rad mv -1 21.6 p 0 ro 0 bW 1 py l CA ac cpt dv g b1 chemdict 0 p sm -.6 lt{-1 -1 ac tr/dy 1.5 0 bs 180 aA x st 0 l 12 dp 2 px 0 OA}{1 0 -8 a}ie}b/WW{gs a}ie}b/BW{wD cp sc xl py dx 2.2 np m}b/dA{[3 L/ix/index st}{Asc p 8 dv}{bd}ie e gr}{gs py rot ne{bW SA s 0 m py sc 1 24.6 3 0 5 DLB 6 cm g x/dx Scientific p n/dx 180 0 360 % userdict/chemdict L/gr/grestore L/tr/transform xl pp l SA RA}{6 -1 st}b/OrA{py -8 py np gs fill e o cp a wy dp 0 In x 5 p sc lp -1 16 m a g -1 2 DA}{dL neg l w px 0 dp/cY mv 2 0 cw py 1 g bW -1 5 px dp type[]type sqrt ac p ChemDraw CopyRight begin/version gs sm sc 8 4 -1 neg}if/px gr cm r fill pA sl pp}{sqrt 0 -1 m2 p DA}{cw gs r -4.8 2 0 arc ix dv o p 1 x -1 x 0 arc l s -9.6 r gi 12 s LB 2 mv py lt{1 2.25 sc e 1 -2 m mv o 0 180 0.6 px p cm mv s dy -1 2 0 gr}{pp}{gs rO 3 exec}{al dv a}b/PT{8 0.5 st}{0 dp L/l/lineto 180 r sm dv/bd s{dp dv dp al m neg ac HA}{dL CB py g lW 0 mv OB dv wF 25.8 rO 1 gs S]}b/dL{dA x dv dp 90 2 p -.6 sc Computing, py w n/dy ac 1 12 neg WI pp 2.2 exec cw sm neg 0 -1 r np b2 sg eq{DB}{DS}ie l CA lp rev{neg}if SA 16 lp st 2 CB 6 wF 0.5 1 2 px SA p mv CA m n wD 1 e LB 0 py begin e 1.2 p px rO sc 5 o dv -9.6 bd neg p -1 x py fill sg -2 cv m x}if at gr p mv a}{ex s sc eq{dp 0 st px DA}{cw xl}{xl OA}{1 e 1 1986, x e l cW L/gs/gsave 1 0 arcn m cX DA}{2.25 np[{py l OA}{1 gs Laser p sg e clip}b/Ct{bs cp l begin L/xl/translate mv aL neg}if/py l 0 16 r n L/mt/matrix wy dv 0 p lx dp gr fill 5 p 2 lp -1.6 ex np setgray 2.25 p cm pp st}b/HA{lW OB at 23 l 0 s 0 sl o 16.8 wy np mv p 1 ne mv fill a -1 1 m bs ly px lfill ac 0 1 cm rlineto arc gr 0 gs p n/ex wx 0 12 py counttomark{bs lp cp bW 90 145 ro 3.375 8 l ac st}{0 1 sg def/b{bind pp sm p dp 0 n aR 1987, 27 1 0 r np gr p bW o e l wx rO Inc. py Prep gr 0 px -1 SA bs ix cm o ac 0.6 sc}b/Ov{OrA bd 0.3 w l dv -1 g 16 cm dp px ac sm OB/bL sc at 5 0 cv ro gs mv cY g/wb 8 fill py 0 pp}ifelse WI gs 0 n 1.6 st aL 1 rad dict 2 sc end}b/Db{bs{dp x ac p clippath e m lp at 0 DA}{dL sc SA n ne{bW mt neg 0 sm 3 p div cm DLB py dp -9.6 m1 1.2 x ne cp pp}{2 L/ie/ifelse gr 1 eq{DD}{DS}ie ey SA sm eq{gs st}{Asc 0 gr}b/OB{/bS m l px g mv cm 1 p 8 ne{bW py s m Cambridge sl 120 p mt 0 lW l bd 27 px dp 270 sc L/mv/moveto 0 p x 2 OA}{1.5 put 1 l 0 rot ro rO -1 cm m fill}b/SA{aF w or{4 dup l}for st n/ey 0 1.5 sm m/w py L/S{sf x DA}{cw p cp m 180 st}{px e bs 2 rad mv 4 bL sm p e 21.6 -1 m 4.8 p 0 ro 0 0 p bW tr def}bind 1 gr py l CA cpt ac dv gi AA}{1 l g p mv rO b1 chemdict 0 p fill sm -.6 4 dp lt{-1 e 2 st}]e py st fill SA l 1 -1 put bd 0 ac 2 wy 1.5 tr/dy st 0 rad l bs ZLB 1 180 aA x al 25.8 st 0 l gs gi 12 dp g/bb dv/bd 2 1 px 0 OA}{1 cp S 0 gr ac end -8 1 a}ie}b/WW{gs a}ie}b/BW{wD cp xl sc 0 1 py rO px 2.2 dx r np gr DA}{270 4 L/ix/index m}b/dA{[3 st}{Asc 8 p dv}{bd}ie pp S e gr}{gs a/py 0 py p al lW rot lt{pp ne{bW -1 0.4 SA 4 s setgray g 0 m cpt w m sc py 1 cm 24.6 0 3 px 39 5 dv DLB gs 6 cm setdash}d/cR ap g np 0 Scientific p x/dx ac n/dx -1 180 pp cv 0 1 x x 360 o gr}b/In{px p -1 sc lp 2 16 -1 p m a -1 g def/L{load dv 2 DA}{dL x}if px OA}{1 neg l m sc 3 px r}if 0 py wb eq{dL}if 0.5 dp s o L/m/mul e x sc mv sm}b/CB{np dv -0.4 cp 5 px l 8 type[]type DT}]o sqrt ac begin/vers gs sm sc 2 4 -1 neg}if/px r ix sl g p rad r -4.8 gs 0 wx xl at lW round arc py 0 x -1 24.6 x arc 0 px 180 S}if/lp s gi 12 sc 4 a s st}{1.0 1 exec LB 2 py mv sg pp 3 2.25 ZLB e sc 1 o 0 0.6 Bd 4 CA dy 3 rO ro}ie}b 0.5 st}{0 -0.4 180 L/l/linet r m/aL g/cX lW lp a/px 1 dv/bd al dp ix w neg ac 0 cm CB py 1 -1 lW 0 OB wF 25.8 fill SA 1 S]}b/ gs 90 2 p pp nH AA}{ Com gr}b 0 9.6 w n/dy ac DA} rO p xl 1 ac 0 n pp 2.2 cw gs -2 r 2 eq{ sg l rev gr} L/n 16 SA lp 6 g 2 sc gr CB cu 6 dx 0.5 1 ap x 36 p SA px 2 OA o/ CA m 3 1 w e x de e be o 1 p x a d 4 p r 1 g 2 o d A l x p s c f l

Enantimeros
CHO CHO CHO

Enantimeros
CHO

OH

HO

HO

OH

OH

HO

OH

HO

CH 2 OH

CH2 OH

CH2 OH currentpoint 192837465

CH2 OH

currentp

D-eritrosa

L-eritrosa

D-treosa

L-treosa

DIASTEROISOMEROS

Monosacridos

Estructura

Aldosas
Cuatro carbonos: Aldotetrosas
D-gliceraldehido

6 nd 120 1 4370 1796 4552 1952 4352 4513 4214 2095 1822 3122 dL DSt 1 1952 [14 59 [12 1345 2047 2086 1878 1904 2736 2756 2580 2606 1033 50 I 3122 I 1345 2464 40 4370 1427 4921 1952 4352 4882 3845 2464 1453 3122 80 3425 1952 2580 40 1714] 2416] 2455] 1878] 1904] 3105] 3125] 2580] 2606] 3425] 20 DSt 1714] DSt chemdict gr [13 [0 II 1453 1952 begin 211 /bs[[1 [1 ]d 2606 gr 1 2 gs 2606 end 1714 120 4370 1796 4552 1952 4352 4513 4214 2095 1822 3122 SP dL DSt 1 1952 DSt DSt [14 54 [12 1345 2047 2086 1878 1904 2736 2756 2580 2606 1033 50 Db [1 I 3122 I 1345 2464 I 40 4370 1427 4921 1952 4352 4882 3845 2464 1453 3122 4370 80 3425 1952 2580 40 1714] 2416] 2455] 1878] 1904] 3105] 3125] 2580] 2606] 3425] 1714 20 DSt 1714] DSt DSt chemdict gr [13 [2 [0I II1952 1453 1952 begin 2416 2606 1714 SP DSt DSt DSt [3 D [

m2 W dv p 1 hemDraw opyRight {6 m A x dict/chemdict p}{sqrt grestore -9.6 r l A}{cw ransform cY OrA{py 2 lt{1 mv -2 m 180 sc px cm p s mv -1 2 0 gr}{pp}{gs exec}{al dv a}b/PT{8 dp sm s{dp dv m HA}{dL g mv dv rO x dp dv -.6 sc py WI neg 12 exec sm 0 -1 neg b2 np CA lp st wF p mv n LB 0 py 1.2 p 5 sc -9.6 bd neg p gr at mv a}{ex p st px e OA}{1 1 1986, e lL/gs/gsave arcn m l Laser gs p cp clip}b/Ct{bs L/xl/translate aL mv neg}if/py ln 0 p ex 5 2 gr np 2.25 pp st}b/HA{lW at OB l0 sl o wy 16.8 p 1 mv 1 -1 m px fill 0 gs n/ex py counttomark{bs 12 lp 145 90 3.375 ro 8 l ac st}{0 sg n aR 1987, 1 r np bW wx py Prep gr -1 SA ix 0.6 ac bd 0.3 dv px dp sc OB/bL ro cv 8 fill aL dict 1 rad end}b/Db{bs{dp x sc p at 0 DA}{dL n 0 neg DLB py dp m1 1.2 -9.6 x 1 L/ie/ifelse gr eq{DD}{DS}ie SA ey 0 l8 ne{bW py m Cambridge 120 p mt bd px dp sc 0 p put rot rO -1 cm m l}for n/ey m/w L/S{sf DA}{cw x p m 180 e 2 rad mv -1 21.6 p 0 ro 0 bW 1 py l CA ac cpt dv g b1 chemdict 0 p sm -.6 lt{-1 -1 ac tr/dy 1.5 0 bs 180 aA x st 0 l 12 dp 2 px 0 OA}{1 0 -8 a}ie}b/WW{gs a}ie}b/BW{wD cp sc xl py dx 2.2 np m}b/dA{[3 L/ix/index st}{Asc p 8 dv}{bd}ie e gr}{gs py rot ne{bW SA s 0 m py sc 1 24.6 3 0 5 DLB 6 cm g x/dx Scientific p n/dx 180 0 360 % userdict/chemdict L/gr/grestore L/tr/transform xl pp l SA RA}{6 -1 st}b/OrA{py -8 py np gs fill e o cp a wy dp 0 In x 5 p sc lp -1 16 m a g -1 2 DA}{dL neg l w px 0 dp/cY mv 2 0 cw py 1 g bW -1 5 px dp type[]type sqrt ac p ChemDraw CopyRight begin/version gs sm sc 8 4 -1 neg}if/px gr cm r fill pA sl pp}{sqrt 0 -1 m2 p DA}{cw gs r -4.8 2 0 arc ix dv o p 1 x -1 x 0 arc l s -9.6 r gi 12 s LB 2 mv py lt{1 2.25 sc e 1 -2 m mv o 0 180 0.6 px p cm mv s dy -1 2 0 gr}{pp}{gs rO 3 exec}{al dv a}b/PT{8 0.5 st}{0 dp L/l/lineto 180 r sm dv/bd s{dp dv dp al m neg ac HA}{dL CB py g lW 0 mv OB dv wF 25.8 rO 1 gs S]}b/dL{dA x dv dp 90 2 p -.6 sc Computing, py w n/dy ac 1 12 neg WI pp 2.2 exec cw sm neg 0 -1 r np b2 sg eq{DB}{DS}ie l CA lp rev{neg}if SA 16 lp st 2 CB 6 wF 0.5 1 2 px SA p mv CA m n wD 1 e LB 0 py begin e 1.2 p px rO sc 5 o dv -9.6 bd neg p -1 x py fill sg -2 cv m x}if at gr p mv a}{ex s sc eq{dp 0 st px DA}{cw xl}{xl OA}{1 e 1 1986, x e l cW L/gs/gsave 1 0 arcn m cX DA}{2.25 np[{py l OA}{1 gs Laser p sg e clip}b/Ct{bs cp l begin L/xl/translate mv aL neg}if/py l 0 16 r n L/mt/matrix wy dv 0 p lx dp gr fill 5 p 2 lp -1.6 ex np setgray 2.25 p cm pp st}b/HA{lW OB at 23 l 0 s 0 sl o 16.8 wy np mv p 1 ne mv fill a -1 1 m bs ly px lfill ac 0 1 cm rlineto arc gr 0 gs p n/ex wx 0 12 py counttomark{bs lp cp bW 90 145 ro 3.375 8 l ac st}{0 1 sg def/b{bind pp sm p dp 0 n aR 1987, 27 1 0 r np gr p bW o e l wx rO Inc. py Prep gr 0 px -1 SA bs ix cm o ac 0.6 sc}b/Ov{OrA bd 0.3 w l dv -1 g 16 cm dp px ac sm OB/bL sc at 5 0 cv ro gs mv cY g/wb 8 fill py 0 pp}ifelse WI gs 0 n 1.6 st aL 1 rad dict 2 sc end}b/Db{bs{dp x ac p clippath e m lp at 0 DA}{dL sc SA n ne{bW mt neg 0 sm 3 p div cm DLB py dp -9.6 m1 1.2 x ne cp pp}{2 L/ie/ifelse gr 1 eq{DD}{DS}ie ey SA sm eq{gs st}{Asc 0 gr}b/OB{/bS m l px g mv cm 1 p 8 ne{bW py s m Cambridge sl 120 p mt 0 lW l bd 27 px dp 270 sc L/mv/moveto 0 p x 2 OA}{1.5 put 1 l 0 rot ro rO -1 cm m fill}b/SA{aF w or{4 dup l}for st n/ey 0 1.5 sm m/w py L/S{sf x DA}{cw p cp m 180 st}{px e bs 2 rad mv 4 bL sm p e 21.6 -1 m 4.8 p 0 ro 0 0 p bW tr def}bind 1 gr py l CA cpt ac dv gi AA}{1 l g p mv rO b1 chemdict 0 p fill sm -.6 4 dp lt{-1 e 2 st}]e py st fill SA l 1 -1 put bd 0 ac 2 wy 1.5 tr/dy st 0 rad l bs ZLB 1 180 aA x al 25.8 st 0 l gs gi 12 dp g/bb dv/bd 2 1 px 0 OA}{1 cp S 0 gr ac end -8 1 a}ie}b/WW{gs a}ie}b/BW{wD cp xl sc 0 1 py rO px 2.2 dx r np gr DA}{270 4 L/ix/index m}b/dA{[3 st}{Asc 8 p dv}{bd}ie pp S e gr}{gs a/py 0 py p al lW rot lt{pp ne{bW -1 0.4 SA 4 s setgray g 0 m cpt w m sc py 1 cm 24.6 0 3 px 39 5 dv DLB gs 6 cm setdash}d/cR ap g np 0 Scientific p x/dx ac n/dx -1 180 pp cv 0 1 x x 360 o gr}b/In{px p -1 sc lp 2 16 -1 p m a -1 g def/L{load dv 2 DA}{dL x}if px OA}{1 neg l m sc 3 px r}if 0 py wb eq{dL}if 0.5 dp s o L/m/mul e x sc mv sm}b/CB{np dv -0.4 cp 5 px l 8 type[]type DT}]o sqrt ac begin/vers gs sm sc 2 4 -1 neg}if/px r ix sl g p rad r -4.8 gs 0 wx xl at lW round arc py 0 x -1 24.6 x arc 0 px 180 S}if/lp s gi 12 sc 4 a s st}{1.0 1 exec LB 2 py mv sg pp 3 2.25 ZLB e sc 1 o 0 0.6 Bd 4 CA dy 3 rO ro}ie}b 0.5 st}{0 -0.4 180 L/l/linet r m/aL g/cX lW lp a/px 1 dv/bd al dp ix w neg ac 0 cm CB py 1 -1 lW 0 OB wF 25.8 fill SA 1 S]}b/ gs 90 2 p pp nH AA}{ Com gr}b 0 9.6 w n/dy ac DA} rO p xl 1 ac 0 n pp 2.2 cw gs -2 r 2 eq{ sg l rev gr} L/n 16 SA lp 6 g 2 sc gr CB cu 6 dx 0.5 1 ap x 36 p SA px 2 OA o/ CA m 3 1 w e x de e be o 1 p x a d 4 p r 1 g 2 o d A l x p s c f l

CHO

CHO

CHO

CHO

OH

HO

HO

OH

OH

HO

OH

HO

CH 2 OH

CH2 OH

CH2 OH currentpoint 192837465

CH2 OH

currentp

D-eritrosa

L-eritrosa

D-treosa
L-gliceraldehido

L-treosa

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Aldosas
Cinco carbonos: Aldopentosas
D-eritrosa
CHO

D-treosa
CHO
CHO CHO

OH

HO

OH

HO

OH

OH

HO

HO

OH

OH

OH

OH

D-ribosa

CH2OH

CH2 OH currentpoint C H OH192837465 C H OH curren currentpoint 192837465 currentpoint 192837

D-arabinosa

D-xilosa

D-lixosa

Monosacridos

Estructura

70[0 /bs[[1 [1 ]d gr 1 end 165 742 746 762 864 638 881 633 I1 759 6 759 4200 4010 2850 4770 3349 3520 4641 4662 2669 100 2487 2181 40 742 746 762 1169 333 1186 328 DSt 80 759 4505] 4010] 3155] 5075] 3349] 3825] 4662] 2669] 40 4010] 3349] 4641] 2669] [1 2487] I 20 746 chemdict 4505 DSt begin [220 1186 SP 4010 DSt DSt[2 [3SP 328 4010 75 /bs[[1 [1 ]d gr Db 1 [0 end 166 3218 3321 3280 3033 3145 3073 3162 3264 3038 3344 3064 I1 3182 123 3182 2092 4150 3961 4720 2589 3470 4591 4613 3271 96 3075 2770 40 3218 3626 3585 2727 3145 2768 3162 3569 2732 3649 2759 DSt 80 3182 40 2397] 4456] 3961] 5026] 2589] 3775] 4591] 4613] 3271] [1 II3075] 3218 chemdict 2397 begin II 3626 2589DSt DSt[4 [3

% userdict/chemdict L/gr/grestore L/tr/transform xl pp l SA RA}{6 -1 st}b/OrA{py -8 py np gs fill e o cp a wy dp 0 In x 5 w dp/cY cw py 1 2 0 g bW -1 dp p ChemDraw CopyRight sc 8 cm gr pA fill pp}{sqrt 0 m2 -1 DA}{cw 2 p 1 p ix dv o l r -9.6 2 lt{1 -2 m mv 180 sc px mv s p cm 2 -1 exec}{al dv 0 gr}{pp}{gs a}b/PT{8 dp sm dv s{dp m g HA}{dL mv dv dp rO x -.6 sc py neg WI 12 exec 0 sm neg -1 b2 np CA lp st wF mv p n LB py 0 1.2 p sc -9.6 p neg 5 bd gr mv at a}{ex p st 1 e OA}{1 px e l 1986, L/gs/gsave arcn m lp gs Laser clip}b/Ct{bs cp aL l mv L/xl/translate neg}if/py 0 n p ex 5 np gr p 2 pp st}b/HA{lW 2.25 l OB at 0 16.8 wy o sl 1 p mv -1 1 px mv m 0 fill gs n/ex py 90 lp counttomark{bs ac l 12 3.375 ro 145 8 sg st}{0 aR n r bW 1 1987, np wx py gr Prep -1 0.6 ix ac SA bd 0.3 dv px dp ro cv sc 8 fill OB/bL aL rad 1 x at end}b/Db{bs{dp sc p dict 0 0 n neg DA}{dL DLB 0 py -9.6 1.2 dp m1 1 gr ey x eq{DD}{DS}ie SA l 0 L/ie/ifelse 8 ne{bW m mt py p 120 Cambridge bd px sc dp 0 p -1 rO cm rot put m l}for n/ey p 180 m/w DA}{cw e m x L/S{sf 2 rad 21.6 -1 mv ro 0 p 0 1 l py bW cpt ac CA dv g b1 0 -.6 p sm chemdict -1 lt{-1 ac tr/dy aA 0 1.5 180 x bs 12 l st 0 x 2 dp px 0 -8 OA}{1 xl sc cp 0 a}ie}b/WW{gs a}ie}b/BW{wD 2.2 py dx 8 np st}{Asc p dv}{bd}ie m}b/dA{[3 gr}{gs py e L/ix/index rot s ne{bW 0 py sc 24.6 m SA 0 1 3 DLB x/dx cm 5 6 g 180 p n/dx Scientific 0 p 360 16 lp sc -1 a neg m -1 g 2 px l DA}{dL 0 mv px sqrt sm ac gs 5 type[]type r 4 -1 neg}if/px -4.8 begin/version 0 gs p sl r x arc 0 arc x s -1 12 gi s LB 1 mv e py 0.6 0 2 sc 2.25 0 o 3 rO dy 0.5 st}{0 180 ac dp neg lW al r dv/bd py CB 25.8 0 OB 1 L/l/lineto gs wF 90 p 2 S]}b/dL{dA w ac 2.2 n/dy cw Computing, pp r sg 16 1 l rev{neg}if 2 lp eq{DB}{DS}ie SA 1 6 CB 0.5 e 2 px m CA 1 e wD SA px begin dv rO cv fill -2 sg -1 p o py s m 0 x sc xl}{xl x}if eq{dp DA}{cw cW x 0 1 e l cX sg OA}{1 np[{py 16 0 wy DA}{2.25 dv r p -1.6 dp begin fill gr cm lx lp np p setgray 0 s 0 mv L/mt/matrix fill 23 a ne np l ly 1 rlineto 0 arc ac cm bs wx gr 0 p bW cp sm 1 27 1 pp p rO l gr def/b{bind 0 o 0 dp cm e px o w sc}b/Ov{OrA at Inc. ac bs mv sm cm gs l -1 16 g 5 py cY 0 1.6 st g/wb pp}ifelse n gs WI ac 2 mt lp 0 clippath 2 m e p cm sc ne{bW sm p gr}b/OB{/bS cp div st}{Asc m 1 px SA ne sm cm 3 eq{gs p pp}{2 g 0 mv 27 s l sl 270 0 ro 1 lW w l 0 fill}b/SA{aF 2 sm st x py or{4 OA}{1.5 dup 1.5 st}{px p cp L/mv/mov 4.8 sm e p 4 0 bs tr bL gr m l rO p AA}{1 mv gi py st}]e l st def}bin 0 fill wy 2 1 SA dp fill e bd rad st 4 ZLB 25.8 2 l put gs 1 0 dv/bd al gr ac cp 1 g/bb rO gi end S 1 gr a/py px 0 r p 1 DA} 4 S lW pp -1 cpt lt{ 0.4 w 4 0 39 px al cm se ap g gs ac SA m np d cv 0 x 1 s p % userdict/chemdict L/gr/grestore L/tr/transform xl pp l SA RA}{6 -1 st}b/OrA{py -8 py np gs fill e o cp a wy dp 0 In x 5 w dp/cY 2 0 cw py 1 g bW -1 dp p ChemDraw CopyRight sc 8 cm gr fill pA pp}{sqrt 0 -1 m2 DA}{cw 2 p ix o dv p 1 l -9.6 r 2 lt{1 -2 m mv 180 sc px p mv s cm -1 2 exec}{al dv 0 gr}{pp}{gs a}b/PT{8 dp sm s{dp dv m HA}{dL g mv dv rO dp x -.6 sc py 12 neg WI exec sm 0 -1 neg b2 np CA lp st wF p mv n LB 0 py 1.2 p 5 -9.6 sc bd p neg gr a}{ex mv at p st e OA}{1 1 px e 1986, l L/gs/gsave arcn m Laser l gs p clip}b/Ct{bs L/xl/translate aL cp l mv neg}if/py n 0 5 p np ex gr 2 pp 2.25 st}b/HA{lW OB l at 0 sl 16.8 wy o p 1 -1 mv m px 0 fill gs n/ex py 90 counttomark{bs 145 lp 12 l 3.375 8 ac ro st}{0 sg n aR 1 r 1987, bW np wx Prep py -1 ix gr SA 0.6 ac 0.3 bd dv dp px sc ro cv 8 OB/bL fill aL 1 dict rad sc x end}b/Db{bs{dp p at 0 0 DA}{dL n neg 0 DLB m1 -9.6 py 1.2 dp 1 eq{DD}{DS}ie gr L/ie/ifelse x SA ey 0 l 8 ne{bW m py 120 Cambridge p bd mt px sc dp 0 p put -1 rot cm rO m l}for 180 n/ey L/S{sf m/w DA}{cw m x p e rad 2 -1 mv 21.6 p 0 ro 0 1 bW l CA py cpt ac dv b1 g 0 sm chemdict -.6 -1 p lt{-1 ac tr/dy 1.5 aA 0 180 bs 0 x 12 st 2 dp l px OA}{1 0 a}ie}b/WW{gs a}ie}b/BW{wD 0 -8 sc xl py cp 2.2 8 st}{Asc m}b/dA{[3 np p L/ix/index dx dv}{bd}ie e gr}{gs py rot s ne{bW SA 0 sc m 0 py 24.6 DLB 3 1 5 6 g 180 cm x/dx p Scientific n/dx 0 360 p 16 -1 lp sc m -1 a 2 g neg DA}{dL l px 0 mv 5 px sqrt begin/version 4 -1 gs type[]type ac sm r gs sl neg}if/px 0 r -4.8 p arc -1 x arc s 0 gi x s 12 LB 1 2 e 2.25 sc mv py 0.6 o 0 0.5 0 3 rO 180 st}{0 dy r L/l/lineto al ac dv/bd neg dp 0 CB py 25.8 lW 1 wF OB gs 90 2 S]}b/dL{dA p Computing, w cw ac pp 2.2 1 n/dy sg r 16 eq{DB}{DS}ie rev{neg}if SA l lp 6 1 CB 0.5 2 CA e wD m SA 2 e 1 px begin px -2 o fill rO -1 sg cv dv s 0 py p m x xl}{xl x}if sc DA}{cw cW eq{dp 1 cX DA}{2.25 OA}{1 0 x sg e 16 dv l begin np[{py r 0 gr fill p -1.6 dp wy L/mt/ma np setgray cm lp lx p 0 s 23 0 ne a fill mv bs np rlineto 1 cm l arc 0 gr ac ly p 0 bW 1 wx cp sm pp def/b 1 27 p dp gr o e l 0 rO Inc p bs o 0 cm px sc} ac sm w -1 gs mv 5 cY g/ cm g 0 16 a n l p 0 g 1 s 0 a

Aldosas

Seis carbonos: Aldohexosas


D-ribosa
CHO CHO CHO

D-arabinosa
CHO

OH

HO

OH

HO

OH

OH

HO

HO

OH

OH

OH

OH

OH

OH

OH

OH

CH2OH

D-alosa

CH2 OH CH2 OH CH2 OH currentpoint 192837465 currentpoint 192837465 currentpoint 192837465 currentp

D-altrosa

D-glucosa

D-manosa

Monosacridos

Estructura

2850 0 5 9 7 1 2 0 55 5898 5473 5920 5044 5441 5874 5030 5458 5858 5034 5022 40 DSt 80 5442 2460] 4477] 3995] 5038] 3339] 3808] 4611] 4632] 2662] [1 40 I3155] 20 5898 chemdict 2662 DSt begin [2 I SP 5473 2460 DSt [3 54414428 4477DSt DSt[3 [4I I8282 59203962 3995DSt DS 70 /bs[[1 [1 ]d gr Db 1 [0 end 161 7835 7981 7707 7802 7819 7918 7697 7998 7723 I1 7842 356 7842 2131 4127 3962 4689 3459 4562 4583 3262 2622 99 3095 2790 40 7835 8282 7406 7802 7819 8219 7396 8298 7422 DSt 80 7842 40 2431] 4428] 3962] 4989] 3759] 4562] 4583] 3262] 2622] [1 20 I3095] 7835 chemdict 2431 DSt begin [2 SP II 7802 eg L arcn }{ex m t 8 gs Laser dict x {gs p l L/xl/translate clip}b/Ct{bs /gs/gsave aL 6 986, A}{1 cp v mv l neg}if/py n 0 5 p 2 ex np gr 2.25 pp st}b/HA{lW OB at lsl 16.8 0 wy o p 1 -1 mv m px 0 fill gs n/ex py 90 12 counttomark{bs 145 lp 8 3.375 l ro ac st}{0 sg n aR 1 r 1987, np bW wx Prep py -1 SA ix gr 0.6 ac bd 0.3 dv dp px sc cv ro OB/bL 8 fill aL rad dict 1 sc x end}b/Db{bs{dp at p 0 DA}{dL 0 n neg 0 DLB -9.6 m1 dp py 1.2 L/ie/ifelse 1 eq{DD}{DS}ie x gr SA 0 ey l 8 ne{bW m py 120 Cambridge p mt bd px dp sc 0 p put -1 rot cm rO m l}for L/S{sf n/ey DA}{cw x m/w 180 m p e rad mv 2 -1 21.6 p 0 ro 0 1 bW py CA l cpt ac dv b1 g chemdict 0 sm -.6 -1 p lt{-1 tr/dy 1.5 0 180 aA bs 0 x st 2 12 dp l px OA}{1 0 -8 a}ie}b/WW{gs a}ie}b/BW{wD xl sc py cp 2.2 m}b/dA{[3 8 L/ix/index dx st}{Asc np p dv}{bd}ie e gr}{gs py ne{bW rot s SA 0 m sc 24.6 py 0 1 3 DLB 6 5 g x/dx p Scientific 180 cm n/dx 0 360 p 16 sc -1 lp m a 2 g neg DA}{dL l px 0 mv px 5 sqrt -1 begin/version 4 type[]type gs ac r sm neg}if/px sl gs -4.8 0 p arc x -1 arc s 0 x gi 12 LB 2 sc e 1 py mv 2.25 o 0.6 0 3 0.5 180 rO dy st}{0 r L/l/lineto dv/bd dp al neg ac 0 CB py 25.8 lW OB wF 1 90 gs S]}b/dL{dA 2 p Computing, w cw 1 ac pp n/dy 2.2 r sg eq{DB}{DS}ie 16 rev{neg}if l SA 6 lp 2 CB 1 0.5 CA wD SA m e 1 2 px begin px -1 o -2 cv dv rO fill sg x s x}if py sc 0 m p xl}{xl DA}{cw eq{dp cW 1 cX x DA}{2.25 0 OA}{1 e sg np[{py begin r 16 l dv 0 -1.6 fill gr p wy dp L/mt/matrix np setgray lp lx cm p s 0 23 0 np ne a bs mv fill arc rlineto l 1 cm 0 ly ac gr p 0 bW wx 1 cp def/b{bind pp sm 27 dp 1 p 0 e o gr l p rO Inc. bs o 0 cm sc}b/Ov{OrA px -1 gs ac w sm mv 5 g/wb cm cY 0 g 16 at l 0 pp}ifelse n 1.6 0 py gs st ac WI e clippath 2 m p sc lp cm ne{bW SA p sm 3 cp mt ne div pp}{2 st}{Asc g 1 gr}b/OB{/bS sm m mv eq{gs cm px l sl 0 27 lW s p 270 2 x 0 1 OA}{1.5 fill}b/SA{aF L/mv/moveto or{4 sm ro st w 0 l 1.5 dup py bs 4 st}{px p e bL sm 4.8 m cp p 0 p gr def}bind tr gi AA}{1 l p st st}]e 2 rO mv e 4 py 1 put 0 SA fill l dp bd fill wy st l 2 1 ZLB 25.8 al rad gs dv/bd g/bb gi 1 gr 0 cp 1 S ac r rO 0 gr 1 4 DA}{270 end px pp S p 0 al a/py 4 0.4 lW -1 cpt SA lt{pp setgray cm g 39 m w dv gs px ap setdash}d/cR ac -1 np 1 cv pp x 0 o -1 1 p 2 dv x}if def/L{load gr}b/In{px OA}{1 m r}if sc e s 3 px 0.5 wb sc o dp sm}b/CB{np[{[{C py mv cp eq{dL}if 8 -0.4 x L/m/mul l dv sc DT}]o g at ix 2 lW xl rad 0 round 24.6 wx 180 py sc px st}{1.0 exec pp 4 1 S}if/lp sg ZLB a 1 3 0 ro}ie}b/AA{np 4 Bd CA -0.4 m/aL g/cX 1 lW a/px w 0 ix cm 1 lp -1 0 pp fill SA AA}{1 nH 9.6 0 p gr}b/wD DA}{180 n gs rO xl ac gr}ie}b/C 2 r -2 sc L/n/neg 6 gr g o/cX currentm ap 360 OA}{1 p 3 def}b/d/ x o x 3 dx 1 1 21.6 ac 12 Ac}{0. dv px 4 g l-1 wb LB cm lp aL o -1 gs s{nH l sg w gi exec ne{p e arc px -1 lt{e d/wF p py x r 0 r gs 2 1 cX 5 al n fill sm s/w 9. m dp s p 1 sc m -1 a 0 L g 2 e C c % userdict/chemdict L/gr/grestore L/tr/transform xl pp l SA RA}{6 -1 st}b/OrA{py -8 py np fill e o cp a wy dp 0 In x 5 w dp/cY 2 0 cw py 1 g -1 dp p ChemDraw CopyRight sc 8 cm gr fill pA pp}{sqrt 0 -1 m2 DA}{cw 2 p ix dv o p 1 l -9.6 r 2 lt{1 -2 m mv 180 sc px mv s cm 2 -1 gr}{pp}{gs exec}{al dv a}b/PT{8 sm s{dp dv m HA}{dL g mv dv rO dv dp x -.6 py 12 neg WI exec sm 0 neg -1 b2 np CA lp st wF p mv n LB py 1.2 p 5 sc -9.6 bd p neg gr a}{ex mv at p st e px OA}{1 1 e 1986, L/gs/gsave lac arcn m l Laser gs p L/xl/translate clip}b/Ct{bs aL cp mv l neg}if/py n 5 p ex np gr 2 pp 2.25 st}b/HA{lW OB at l 0 sl 16.8 wy o 1 -1 mv m px 0 fill gs n/ex 90 145 counttomark{bs 12 lp 3.375 l 8 ro ac st}{0 sg n aR 1 r 1987, np bW wx Prep py ix SA gr 0.6 0.3 ac bd dv dp sc ro cv OB/bL 8 fill aL dict 1 rad sc x end}b/Db{bs{dp at DA}{dL 0 n neg 0 DLB py m1 dp -9.6 1.2 1 L/ie/ifelse eq{DD}{DS}ie gr SA ey 0 l 8 ne{bW m py 120 Cambridge p mt bd px sc dp 0 p put -1 rot rO cm m l}for n/ey L/S{sf 180 m/w DA}{cw x m e rad 2 mv -1 21.6 p 0 ro 0 1 bW py CA cpt ac dv b1 g chemdict 0 sm -.6 -1 p lt{-1 ac tr/dy 1.5 0 aA 180 bs 0 st 12 2 dp l px OA}{1 0 a}ie}b/WW{gs a}ie}b/BW{wD -8 sc xl py cp 2.2 m}b/dA{[3 8 st}{Asc dx np L/ix/index p dv}{bd}ie e gr}{gs py rot s ne{bW SA 0 m sc py 24.6 3 DLB 1 5 6 g x/dx 180 p cm Scientific n/dx 0 360 p 16 -1 lp sc m -1 a 2 g neg DA}{dL l px 0 mv 5 px sqrt begin/version -1 4 type[]type gs ac sm r sl gs neg}if/px r -4.8 p arc x -1 arc s gi x s 12 LB 2 2.25 e sc 1 py mv o 0.6 0 0.5 3 rO 180 dy st}{0 r L/l/lineto dv/bd al dp neg ac 0 CB py lW wF 25.8 OB gs 90 S]}b/dL{dA 2 p Computing, w cw ac pp 1 n/dy 2.2 sg r eq{DB}{DS}ie 16 rev{neg}if l SA lp 6 2 CB 1 0.5 CA wD m e SA 2 px 1 begin px -2 o -1 rO fill dv sg cv s py x m 0 x}if p xl}{xl sc DA}{cw eq{dp cW 1 cX x DA}{2.25 OA}{1 sg e np[{py begin 16 dv l r 0 gr fill p dp -1.6 wy L/mt/matrix np setgray lp lx cm p 23 s 0 ne a np mv fill bs rlineto 1 l arc cm ly gr ac p 0 bW wx 1 cp def/b{bind pp sm 1 dp 27 p o gr e 0 l rO p Inc. bs 0 cm sc}b/Ov{OrA px -1 w sm ac gs mv 5 cY g/wb cm g 0 16 at l n pp}ifelse 0 gs 0 1.6 st ac WI e m 2 clippath 2 p sc lp p cm ne{bW SA sm cp mt ne 3 st}{Asc pp}{2 div g 1 gr}b/OB{/bS sm m cm eq{gs mv sl l 0 s lW p 27 270 2 x 0 1 fill}b/SA{aF OA}{1.5 L/mv/moveto or{4 st sm ro w 0 1.5 l py dup st}{px bs 4 p e sm bL cp m 4.8 p gr def}bind tr gi l AA}{1 p st}]e st rO mv py 2 e 4 1 SA l 0 fill put dp bd fill st wy l ZLB 2 rad al gs 25.8 g/bb dv/bd gi 1 gr 0 cp 1 ac r rO S 0 gr DA}{ 1 end px 4 pp S p 0 4 al a/py -1 lW 0.4 cpt SA lt{p setg cm 39 w g m dv px ap np ac set 1 -1 cv pp 0 x o -1 p 2 m d r x O s

Aldosas

Seis carbonos: Aldohexosas


D-xilosa
CHO CHO CHO

D-lixosa
CHO

OH

HO

OH

HO

OH

OH

HO

HO

HO

HO

HO

HO

OH

OH

OH

OH

C H 2OH

D-gulosa

currentpoint C 192837465 C H OH H OH currentp currentpoint C H 192837465 OH currentpoint 192837465


2

D-idosa

D-galactosa

D-talosa

Monosacridos

Estructura
Aldosas Cetosas Estructura cclica

Monosacridos

Estructura

Cetosas
Tres carbonos: Cetotriosa
CH2 C O CH2 OH
Dihidroxiacetona

OH

Monosacridos

Estructura

Cetosas
Cuatro carbonos: Cetotetrosas
CH2 OH C O H C OH CH2 OH
CH2 OH C O HO C H CH2 OH

D-eritrulosa

L-eritrulosa

Monosacridos

Estructura

Cetosas
Cinco carbonos: Cetopentosas
CH2OH C O H C OH H C OH CH2OH CH2OH C O HO C H H C OH CH2OH

D-ribulosa

D-xilulosa

Monosacridos

Estructura

Cetosas
Cinco carbonos: Cetopentosas
CH2OH C O H C OH H C OH H C OH CH2OH CH2OH C O HO C H H C OH H C OH CH2OH CH2OH C O H C OH HO C H H C OH CH2OH CH2OH C O HO C H HO C H H C OH CH2OH

D-psicosa
D-ribulosa

D-fructosa

D-Sorbosa
D-xilulosa

D-tagatosa

Monosacridos

Estructura
Aldosas Cetosas Estructura cclica

Monosacridos

Estructura

Estructura cclica
H C R
Aldehido

OH

+ +

R OH
Alcohol

H C OR R
Hemiacetal

C R

OH

+ +

R OH
Alcohol

C OR R

Cetona

Hemicetal

Monosacridos

Estructura

Estructura cclica
HO C H H C OH HO C H H C OH H C CH 2OH O
H C H C OH HO C H H C OH H C OH CH2OH O

H C OH H C OH HO C H H C OH H C CH 2OH O

-D-glucopiranosa
Anillo de 6 miembros

D-glucosa

-D-glucopiranosa

Como el del pirano piranosas


O

Monosacridos

Estructura

Estructura cclica
HO C CH 2OH HO C H H C OH H C CH 2OH
Anillo de 5 miembros furanosas

HOCH2 C

O
HOCH2 C OH O HO C H H C OH H C CH 2OH

HO C H H C OH H C OH CH2OH
D-fructosa

Como el del furano

Monosacridos

Estructura

Estructura cclica
HO C H H C OH HO C H H C OH H C CH 2OH O
CH 2OH O H H HO OH H OH H H OH

Estructura en proyeccin de Fischer

Estructura en proyeccin de Haworth

Monosacridos

Estructura

Estructura cclica
HO C H H C OH HO C H H C OH HOCH2 C H O
CH 2OH O H H HO OH H OH H H OH

Estructura en proyeccin de Fischer Una permutacin Inversin en C5

Estructura en proyeccin de Haworth

Monosacridos

Estructura

Estructura cclica
HO C H H C OH HO C H H C OH HOCH2 C H O
CH 2OH O H H HO OH H OH H H OH

Estructura en proyeccin de Fischer Dos permutaciones Igual configuracin

Estructura en proyeccin de Haworth

Monosacridos

Estructura

Estructura cclica
HO C H H C OH HO C H H C OH HOCH2 C H O
CH 2OH O H H HO OH H OH H H OH

Estructura en proyeccin de Fischer

Estructura en proyeccin de Haworth

Los sustituyentes a la izquierda en Fischer estn hacia arriba en Hawort

Monosacridos

Estructura

Estructura cclica
CH 2OH O H H HO OH H OH H H OH

HO

CH2OH O

HO HO OH

Estructura en proyeccin de Haworth

Conformacin silla

Monosacridos

Estructura

Estructura cclica
CH 2OH O H H HO OH H OH H H OH

C4
HO CH2OH O HO HO OH

C1 Conformacin silla C41 o tambin C1

Estructura en proyeccin de Haworth

Monosacridos

Estructura
C1
OH

Estructura cclica
C4
HO CH2OH O HO HO OH

CH2OH

C4

OH O OH OH

C1 C41 o tambin C1

C14 o tambin 1C

Casi todas las D-piranosas tienen la conformacin C41 y casi todas las L-piranosas tienen la conformacin C14 (Reeves - 1950)

Monosacridos Estructura Reacciones y derivados Aislamiento y anlisis