Carbohydrates. Carbohydrate hydrate of carbon – C n (H 2 O) m Glucose -blood sugar- C 6 H 12 O 6...

Carbohydrates

Carbohydrate

• hydrate of carbon – Cn(H2O)m

• Glucose -blood sugar- C6H12O6 or C6(H2O)6

• Sucrose -table sugar- C12H22O11 or C12(H2O)11

• Not all carbohydrates have this exact form

– old habits die slow or sometimes never at all

Monosaccharides

• Formula CnH2nOn • One carbon is either an aldehyde or

ketone• The suffix ose indicates that the

molecule is a carbohydrate• Use prefix to indicate number of

carbons tri , tetr, pent, hex• Aldose – contain an aldehyde group• Ketose – contain a ketone group

Monosaccharides

• Aldohexoses

Aldohexosesaldehyde function

six carbons

carbohydratesor

saccharides

other examples: ketotetrose, aldotriose, ketopentose

Fischer Projections

• Emil Fischer (late 1800’s)

– Side groups come out of the plane (towards you)– Vertical groups go back away from you

HHO

CHO

HHO

CH2OH

H OH

CHO

H OH

CH2OH

OHH

CHO

HHO

CH2OH

HO H

CHO

H OH

CH2OH

A B C D

Naming Aldotriose and aldotetrose

Remember ET goes home left at T

Naming AldoPentose

RAXL – Ribose, Araginose, Xylose, Lyxose

Right – Top – Middle – Top/Middle

Naming Aldohexoses

• All Altrose Gladly Make Gum in Gallon Tanks

• Bottom – all right

• 2 up – 4x4

• 3 up – 2x2 like Noahs Ark

• 4 up – alternate

R/S and D/L

• R = D - dextrorotatory

• S = L - levarotatory• D – A monosaccharide with the

Penultimate OH group on the right in a Fischer Projection

• L - A monosaccharide with the penultimate OH group on the left in a Fischer Projection

OK, so what’s a penultimate????

Ketoses

• Note:

The ketone is located

on carbon #2

triose

tetrose

pentoses

hexoses

*

*

Penultimate is the nextTo last carbon

Amino Sugars

• Contain an NH2 group instead of an OH

• 1st three are common in nature

Cyclic structure of monsacharides

• It’s the hemiacetal reaction all over

• We draw them as Haworth Projections

• Practice practice practice

From yahoo images

Reactions of Monosacharides

• Practice

From yahoo images

The two Most Significant Sugars

• Ketose

– D-Fructose

– Known as “fruit sugar”

– Found combined with glucosein the disaccharide sucrose

HO

D-fructose

CH2OH

CH2OH

OH

O

OH

•Aldose -D-glucose

-The most important monosaccharide -White solid -Formula C6H12O6

- Sugar used in our bodies

CH2OH

C

C

C

C

C

OH

OH

H

OH

H

O

H

HO

H

H

1

2

3

4

5

6

Multiple Sugars

• Monosaccharides – Single Carbohydrate unit• Disaccharides - two monosaccharides combined• Oligosaccharides - three to ten monosaccharides• Polsaccharide – More than ten monoscharides

Three Disaccharides

• Sucrose

• Lactose

• Maltose

Disaccharides

• Sucrose– A disaccharide– One D-glucose and

one D-Fructose– Connected by two anomeric carbons:

C-1 on glucose and C-2 on fructose linkages: linkage on glucose and linkage on fructose

D-glucose

O

D-fructose

*

Disaccharides

• Sucrose– Anomeric C are tied-up

on both sugars– No oxidation can occur

no hemi-acetals– Sucrose is a

non-reducing sugar– Hydrolyzed by enzymes to form a mixture of

glucose and fructose - “invert sugar”

D-glucose

O

D-fructose

*

Disaccharides

• Sucrose

-D-glucose

O

CH2OHHO

OH

HOCH2

O

O

OHHO

HO

HOCH2

-D-fructose

-C-1

-C-2

*

Disaccharides

• Lactose– A disaccharide

– One D-galactose andone D-glucose

– Connected by an linkagebetween D-Galactose C-1 and D-Glucose C-4

– Known as an -1,4 linkage– Found in mammalian milk

D-galactose

O

D-glucose

*

Disaccharides

O

OH

OHHO

HOCH2 O

OH

OHHO

HO

HOCH2+

O

OH

OHHO

HOCH2

O

O

OHHO

HOCH2

Galactose

-D-galactose -D-glucose

-1,4 linkage

Lactose

Disaccharides

• Maltose– A disaccharide

– Two D-glucose monomers

– Connected by an linkagebetween C-1 and C-4

– Known as an -1,4 linkage (two D-glucose molecules)

– An ingredient in most syrups– “Malt sugar”

D-glucose

O

D-glucose

*

Disaccharides

O

OH

OHHO

HO

HOCH2 O

OH

OHHO

HO

HOCH2+

O

O

OHHO

HO

HOCH2

O

OH

OHHO

HOCH2Maltose

-D-glucose -D-glucose

-1,4 linkage

Polysaccharides

• Starch - Amylose– Many units of -D-glucose– Linkages are -1,4 (same as Maltose)

– Between 1000-2000 glucoseunits (polyglucose)

– Random coils or helix

*

Polysaccharides

• Starch - Amylopectin– Also many units of -D-glucose– Linkages are -1,4 and -1,6– Lots of branching– 20 to 25 glucose monomers in

the straight chain and then branching– A total of 105 to 106 glucose molecules– Use Iodine (I2) to test for starches

*

Polysaccharides

• Glycogen– Animal energy storage (about 400 g in us)

– -D-glucose polymer– Similar to amylopectin but smaller chains– Linkages are -1,4 and -1,6 (branching)– 10 to 20 glucose monomers in the

straight chain and then branching– A total of 105 to 106 glucose molecules

*

Polysaccharides

• Cellulose– Linear polymer of D-glucose– Linkages are -1,4 !– The most abundant molecule in

living tissues– Cotton is about 95% cellulose– 300 to 3000 glucose units– Form fibrous rods

*

Polysaccharides

• Cellulose– We cannot digest cellulose

• glucose linkages!• Many bacteria and fungi

have necessary enzyme• Ruminant mammals carry

these bacteria• Termites also have necessary

microorganisms

*

O

O

O

HOCH2

OH

OH

OH

OH

HOCH2

)(O O

OHOCH2

OH

OH

OH

OH

HOCH2

)

(Starch

alpha linkage Cellulose beta linkage