294710171013carbohydrate bag 2

8/10/2019 294710171013Carbohydrate Bag 2

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1

Structural representationof sugars

Fisher projection:

straight chain representation

Haworth projection:

simple ring in perspective

Conformational representation: chair

and boat configurations

H

OH

OH

OH


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2

Rules for drawing Haworth

projections

if the substituent is to the right in the Fisher

projection, it will be drawn downin the

Haworth projection (Down-Right Rule)

for D-sugarsthe highest numbered carbon

(furthest from the carbonyl) is drawn up. For

L-sugars, it is drawn down

for D-sugars, the OH group at the anomeric

position is drawn down for and up for b.

For L-sugars is up and bis down


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3

H

6

5

4

3

2

1C

C

CC

C

CH2OH

OHH

HOOHH

OH

H

H

O

D-Glucose

-

+

H-

+

OOH

C

C C

C

OC

CH2OH

H

OH

H

H

H

OH

H

OH

1

23

4

5

6

Hemiacetal cyclic( Haworth projection)

- D - Glucopyranose

Fischer projection Haworth projection

Chair conformation

cyclization

for D-sugars the highest numbered carbon (furthest from

the carbonyl) is drawn up. For L-sugars, it is drawn down

for D-sugars, the OHgroup at the anomeric

position is drawn down for

and up forb

. For L-

sugars is up and bis

down

if the substituent is to the right in the

Fisher projection, it will be drawn down in

the Haworth projection (Down-Right Rule)

H

OH

OH

OH


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4

O

OH

C1

C

C

C

C5

CH2OH

OHH

HHO

OHH

H

H O

C1

C2

C3

C4

C5

C6H2OH

OHH

HHO

OHH

OHH

HH

O

C1

C

C

C

C5

CH2OH

OHH

HHO

OHH

H

HO

OH

OH

HChair conformation

D-glucose

b

-D-glucopyranose-D-glucopyranose

Chair conformation

Anomeric carbonOH lactol = OHglycosidic

REDUCING SUGAR


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5

crystallize below 980C crystallize above 980C

[ a] + 52.50

MUTAROTATION

b-D-Glucopyranosea-D-Glucopyranose

O

OH

C

C

C

C

C

CH2OH

OHH

HHO

OHH

H

H O

C

C

C

C

C

CH2OH

OHH

HHO

OHH

OHH

H

H

O

C

C

C

C

C

CH2OH

OHH

HHO

OHH

H

HO


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6

Cyclization of D-fructose

=a-D-fructofuranose

b-D-fructofuranose


7/20


8/20

8

Simplest Carbohydrate - Quiz

CH2OHC=O

CH2OH

Is this a polyhydroxy aldehyde? NO

Is this a polyhydroxy ketone? YES

Is this a D sugar?

Is this a carbohydrate? YES

NO

Is this an L sugar? NO

Why? center in the molecule

Name? Dihydroxy

Acetone


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9

CHO

C

C

CH2OH

1

2

3

4

OH

Reducing

group

D orientation

Primary

alcohol

Primary

alcohol

Primaryalcohol

Reducing

group

CH2OH

C=O

C

CH2OH

1

2

3

4

OH

Aldose Ketose

Anatomy of a Monosaccharide


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10

C

OH

Monosa 2Monosa 1

C

OH

1. C- OH glycosidic vs C - OH alcohol

monosa 1 monosa 2

C O C

a-D-Glucopyranose

O

OH

CH2OH

OH

O H

HO

1

23

4

56

O

OH

CH2OH

OH

OH

1

23

4

56

HO

Lactol

Lactol

a-D-Glucopyranose

H2O-

O

O

CH2O H

OH

OH

HO

1

23

4

5

6

4

O

OH

CH2OH

OH

OH

1

23

5

6

freelactol

a-D-Glucopyranose a-D-Glucopyranose

4-o-(a -D-Glucopyranosyl)- a-D-Glucopyranose

Maltose

REDUCING SUGAR. WHY ?

O

OH

C1

C

C

C

C5

CH2OH

OHH

HHO

OHH

H

H O

C1

C2

C3

C4

C5

C6H2OH

OHH

HHO

OHH

OHH

HH

O

C1

C

C

C

C5

CH2OH

OHH

HHO

OHH

H

HO

OH

OH

HChair conformation

D-glucose

b

-D-glucopyranose-D-glucopyranose

Chair conformation

OH lactol = OHglycodic

REDUCING SUGAR

a-1,4 glucosidic
http://localhost/var/www/apps/conversion/tmp/scratch_5/REDUCING%20SUGAR%20KKI%20LK.ppthttp://localhost/var/www/apps/conversion/tmp/scratch_5/REDUCING%20SUGAR%20KKI%20LK.ppthttp://localhost/var/www/apps/conversion/tmp/scratch_5/REDUCING%20SUGAR%20KKI%20LK.ppthttp://localhost/var/www/apps/conversion/tmp/scratch_5/REDUCING%20SUGAR%20KKI%20LK.ppthttp://localhost/var/www/apps/conversion/tmp/scratch_5/REDUCING%20SUGAR%20KKI%20LK.ppt


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11

Lactose

Lactose is:

Also called milk

sugar. Composed of

galactose and

glucose linkedby a -1,4-glycosidic bond.

4-O-(-D-galactopyranosyl)-D-glucopyranose


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12

2. C- OH glycosidic vs C - OH glycosidic

monosa 1 monosa 2

C O C

Lactol

O

OH

C H2O H

O H

O H

HO

1

23

4

5

6

O

O H

HO

HO C H2

C H2OH

2

1

6

5

34

Lactol

a-D-Glucopyranose

b-D-Fructofuranose

OH

- H2O

O

O

C H2O H

O H

O H

HO

1

23

4

5

6

O

O H

HO

HO C H2

CH2OH

2

1

6

5

34

a-D-Glucopyranose

b-D-Fructofuranose

a-D-Glucopyranosyl-b-D-fructofuranosideor

b-D-Fructofuranosyl - a-D-Glucopyranosid

Sucrose/saccarose

Glucose + fructose sucrose

NON REDUCING SUDAR. WHY ?


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13

Sucrose> also known as tablet sugar

> commercially obtained from sugarcane or sugar beet

>hydrolysis yield glucose and fructoseinvert sugar(invert sugar) Sugar cane

Sugar beet

> used pharmaceutically to make

syrups, troches

Sucrose H2O,H+

Hydrolysis

D

fructose

( -92,40 )

D-glucose( + 52,50)

+

- 39 ,70+ 66,50 INVERT
http://localhost/var/www/apps/conversion/tmp/scratch_5/MUTAROTASI%20D-GLUKOSA%20LK2.ppthttp://localhost/var/www/apps/conversion/tmp/scratch_5/MUTAROTASI%20D-GLUKOSA%20LK2.ppthttp://localhost/var/www/apps/conversion/tmp/scratch_5/MUTAROTASI%20D-GLUKOSA%20LK2.ppthttp://localhost/var/www/apps/conversion/tmp/scratch_5/MUTAROTASI%20D-GLUKOSA%20LK2.ppthttp://localhost/var/www/apps/conversion/tmp/scratch_5/MUTAROTASI%20D-GLUKOSA%20LK2.ppt


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14

Cellobiose

Two glucose units linked 1-4. Disaccharide of cellulose.

A mutarotating, reducing sugar.

=>


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15

Gentiobiose

Two glucose units linked 1-6. Rare for disaccharides, but commonly

seen as branch point in carbohydrates.

=>


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16

monosaccharide condensation polimer

white solid

less water soluble

not sweet

non aldose / ketose

+.

OH

monosacch

OH

+.

monosacch monosaccsmonosacch

OH OH OH OH OH OH

+

O O O

3 H2O


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17

Exp ; polysaccharide from glucose monomerlinked glikosidic (1,4)

OH lactol a

OH lactol a OH lactol a

OH alcohol

O OOO

O OO O

O

OO

1 4 1 4 1 4 1 4

Simple molecular structureO

CH2OH

OO

n


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18

I. Function1. Structural Polysaccharideexp : selulose, chitin dan pectin

2. Nutrition Polysaccharideexp : amylum, glycogen, inulin

3. Others

polysaccharide attached to others.

exp : Heparin, hialuronic acid


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19

II. Hydrolysis1. Homopolysaccharide

produces one kind of monosacch on

hydrolysis

glucosan glucose

fructosan fructose

galactan galactosearaban arabinose

pentosan pentose

heksosan heksose

2. Heteropolysaccharide

produces other substances on hydrolysis


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294710171013carbohydrate bag 2

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