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Carbohydrates

They have the molecular formulas Cn(H2O)n

Compounds that can be hydrolyzed to polyhydroxy


aldehydes or polyhydroxy ketones are also classified as
carbohydrates

Simple Carbohydrates Are Monosacharides


Complex carbohydrates contain two or more sugar units
linked together
disaccharides
oligosaccharides
polysaccharides

Polyhydroxy aldehydes are aldoses


Polyhydroxy ketones are ketoses

Aldoses and Ketoses


aldo- and keto- prefixes identify the nature of
the carbonyl group
-ose suffix designates a carbohydrate
Number of Cs in the monosaccharide indicated
by root (-tri-, tetr-, pent-, hex-)

Four Carbon Aldoses


Aldotetroses have two chirality centers
There are 4 stereoisomeric aldotetroses, two pairs of enantiomers: erythrose
and threose
D-erythrose is a a diastereomer of D-threose and L-threose

D and L notations are used to describe the configurations


of carbohydrates

Configurations of Aldoses
Aldotetroses have two asymmetric carbons and
four stereoisomers

A ketose has one less asymmetric carbon than


aldoses, therefore they have fewer stereoisomers

Diastereomers that differ in configuration at only one


asymmetric carbon are called epimers

Cyclic Structure of Monosaccharides


Hemiacetal Formation

anomer

anomer

The specific rotation of pure -D-glucose or -D-glucose


changes over time to reach an equilibrium (mutarotation)

The structures of cyclic sugars are best represented by


the Haworth projections

Haworth projections allow us to see the relative


orientation of the OH groups in the ring

Ketoses also exist predominantly in cyclic forms

-D-Glucose Is More Stable

-D-glucose is the predominant form at equilibrium

Redox Reactions of Monosaccharides


The carbonyl of aldoses and ketoses can be reduced by
the carbonyl-group reducing agents

Oxidation
The aldehyde groups can be oxidized by Br2

Ketones and alcohols cannot be oxidized by Br 2

In a basic solution, ketoses are converted into aldoses

A strong oxidizing agent such as HNO3 can oxidize the


aldehyde and the alcohol groups

Acylation of Monosaccharides
The OH groups of monosaccharides show the chemistry
of typical alcohols

Alkylation of the OH Groups

Formation of Glycosides

The acetal (or ketal) of a sugar is called a glycoside

Mechanism of Glycoside Formation

The carbon chain of an aldose can be increased by one


carbon in a KilianiFischer synthesis
(Better yield)

imine

reduction

hydrolysis

The Ruff degradation shortens an aldose chain by one


carbon

Preparation of the Calcium D-Gluconate for the


Ruff Degradation

Ruff degradation

Disaccharides
Composed of two monosaccharide subunits hooked
together by an acetal linkage

In -maltose, the OH group bonded to the anomeric


carbon is axial
Maltose is a reducing sugar

In cellobiose, the two subunits are hooked together by a


-1,4-glycosidic linkage

Cellobiose is a reducing sugar

In lactose, the two different subunits are joined by a


-1,4-glycosidic linkage

Lactose is a reducing sugar

The most common disaccharide is sucrose

Sucrose is not a reducing sugar

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