Carbohidratos

Introducción

Monosacáridos

Oligosacáridos

Polisacáridos
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Carbohidratos

Celulosa n

Pedro Antonio García Ruiz

Catedrático de Escuela Universitaria Profesor Titular de Universidad
Area Química analítica Area Química Orgánica

17/07/2018 Departamento deCHÁVEZ

Ms.C. LUIS QuímicaABANTO
Orgánica - Universidad de Murcia
 Carbohidratos
Introducción

Monosacáridos

Oligosacáridos

Polisacáridos
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Introducción
¿Que es un carbohidrato?

Son polihidroxi aldehídos o cetonas o

compuestos que conducen a ellos por hidrólisis
y sus derivados.

Se denominan Hidratos de carbono por

responder muchos de ellos a la formula
empírica:

C (H2O)n
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Introducción
¿Que es un carbohidrato?

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

6 CO2 + H2O

C6(H2O)6 + 6 O2
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Introducción
¿Como se clasifican?
C
a Aldosas
r Monosacáridos
b
Azúcares Cetosas
o
h
-2 Di
i Oligosacáridos
-3 Tri
d
r -4 tetr
a -5 pent
t Polisacáridos
-6 Hex
o
- 7 Hept
s 17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Introducción
¿Para qué sirven?

- Como principios inmediatos son soportes de la vida

Alimento Cultura Alcohol
- Proporcionan: Casa Higiene Medicina

Vestido Comodidad Decoración

- Muchas Polímeros Furfural Políesteres

aplicaciones en
Sintesis Conserva Farmacia
la industria
Química Quiral Celulosa Bebidas

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Carbohidratos
Introducción

Monosacáridos

Oligosacáridos

Polisacáridos
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Monosacáridos

Estructura

Reacciones y derivados

Aislamiento y análisis
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Monosacáridos
Estructura

Aldosas

Cetosas

Estructura cíclica

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura

Aldosas
Tres carbonos: Aldotriosas

CHO CHO

H C OH HO C H

CH2 OH
CH2 OH

D (+) L (-) currentpoint 192

Gliceraldéhido

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura
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Enantiómeros Enantiómeros
CHO CHO CHO CHO

H C OH HO C H HO C H H C OH

H C OH HO C H H C OH HO C H

CH2 OH CH2 OH CH2 OH CH2 OH

currentpoint 192837465 currentpoin
D-eritrosa L-eritrosa D-treosa L-treosa

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

DIASTEROISOMEROS
 Monosacáridos Estructura
Aldosas
dL
20
DSt
370
796
552
952
352
513
214
095
822
122
1 1952
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D-alosa D-altrosa D-glucosa D-manosa
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fill
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Seis carbonos: Aldohexosas

D-xilosa D-lixosa
C HO
CHO C HO
C HO

H C OH
HO C H OH HO C H
H C

H C OH HO H
H C OH C
HO C H

HO C H
HO C H HO C H
HO C H

H C OH
H C OH H C OH
H C OH

C H 2OH currentpoint 192837465

currentpoint 192837465 currentpoin
C H OH
C H OH currentpoint 192837465
C H OH 2
2
2

D-gulosa
17/07/2018
D-idosa D-galactosa
Ms.C. LUIS CHÁVEZ ABANTO
D-talosa
 Monosacáridos
Estructura

Aldosas

Cetosas

Estructura cíclica

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura
Cetosas
Tres carbonos: Cetotriosa

CH2 OH
C O
CH2 OH
Dihidroxiacetona

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

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

D-eritrulosa L-eritrulosa

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

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

D-ribulosa D-xilulosa

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura
Cetosas
Cinco carbonos: Cetopentosas

CH2OH CH2OH CH2OH CH2OH

C O C O C O C O
H C OH HO C H H C OH HO C H
H C OH H C OH HO C H HO C H
H C OH H C OH H C OH H C OH
CH2OH CH2OH CH2OH CH2OH

D-psicosa D-fructosa D-Sorbosa D-tagatosa

17/07/2018 D-ribulosa Ms.C. LUIS CHÁVEZ ABANTO

D-xilulosa
 Monosacáridos
Estructura

Aldosas

Cetosas

Estructura cíclica

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura
Estructura cíclica
OH
H O
C + R OH H C OR
R´ R´
Aldehido + Alcohol Hemiacetal

OH
R´ O
C + R OH R´ C OR
R´ R´
Cetona + Alcohol Hemicetal

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura
Estructura cíclica

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

b-D-glucopiranosa D-glucosa a-D-glucopiranosa

Anillo de 6 miembros Como el del pirano

O
17/07/2018
piranosas
Ms.C. LUIS CHÁVEZ ABANTO
 Monosacáridos Estructura
Estructura cíclica

HOCH2 O
HO C CH2OH HOCH2 C OH
C
HO C H O HO C H O
HO C H
H C OH H C OH
H C OH
H C
H C
H C OH CH2OH
CH2OH
CH2OH

b-D-fructofuranosa D-fructosa a-D-fructofuranosa

Anillo de 5 miembros Como el del furano

furanosas O
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Monosacáridos Estructura
Estructura cíclica
CH2OH
HO C H O
H C OH H H OH
O
HO C H OH H H
HO
H C OH
H C H OH

CH 2OH

Estructura en proyección de Estructura en proyección de

Fischer Haworth

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura
Estructura cíclica
CH2OH
HO C H O
H C OH H H OH
O
HO C H OH H H
HO
H C OH
HOCH2 C H OH
H

Estructura en proyección de Estructura en proyección de

Fischer Haworth
Una permutación
Inversión en C5
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Monosacáridos Estructura
Estructura cíclica
CH2OH
HO C H O
H C OH H H OH

HO C H O OH H H
HO
H C OH
HOCH2 C H H OH

Estructura en proyección de Estructura en proyección de

Fischer Haworth
Dos permutaciones
Igual configuración
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Monosacáridos Estructura
Estructura cíclica
CH2OH
HO C H O
H C OH H H OH

HO C H O OH H H
HO
H C OH
HOCH2 C H H OH

Estructura en proyección de Estructura en proyección de

Fischer Haworth

Los sustituyentes a la izquierda en Fischer

están hacia arriba en Hawort
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO
 Monosacáridos Estructura
Estructura cíclica
CH2OH
O HO CH2OH
H H OH
O
OH H H HO
HO
HO OH
H OH

Estructura en proyección de
Haworth Conformación silla

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura
Estructura cíclica
C4
CH2OH
O HO CH2OH
H H OH
O
OH H H HO
HO
HO OH
H OH
C1
Estructura en proyección de
Haworth Conformación silla
C41 o también C1

17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO

 Monosacáridos Estructura
Estructura cíclica
C4 C1
OH
HO CH2OH CH2OH
O C4 OH O
HO
HO OH OH
OH
C1

C41 o también C1 C14 o también 1C

Casi todas las D-piranosas tienen la conformación C41

y casi todas las L-piranosas tienen la conformación C14
17/07/2018
(Reeves - 1950)
Ms.C. LUIS CHÁVEZ ABANTO
 Monosacáridos

Estructura

Reacciones y derivados

Aislamiento y análisis
17/07/2018 Ms.C. LUIS CHÁVEZ ABANTO