Carbohydrates

Review of sugar nomenclature:


D-Glucose
L-Glucose
Rosanoff-Hudson Rule

Monosaccharides

Trioses - C3

Glyderaldehyde

Tetroses - C4

Erythrose
Threose

Pentoses C5

Ribose
Arabinose
Xylose
Lyxose

Hexose C6

Aldoses


Glucose

Galactose

Ketoses

Fructose

Sorbose

Optical Rotation

+ dextro - right
- levo - left


Haworth Perspective
Cis-Trans isomerization




Glucose isomers in aqueous solutions:

Intensity of Carbonyl band - O-Fructose inwater as a function of temperature:

Fructose isomers in aqueous solutions:





Open chain form of fructose:

Increases with increasing temperature - 20-80° C
Increases 12 x at pH 7.0 when temperature increases from 30-80° C
Temperature effect is reversible 20-80° C
Carbonyl peak is maximal after 10 minutes at any given temperature


Mutarotation

% distribution at 20° C

Sugar

Pyranose

Furanose

 

alpha

beta

alpha

beta

D-Glucose 31-37 64-68 0.5 0.5
D-Galactose 30-35 64-70 1 3
D-Mannose 64-69 31-36    
D-Fructose 4 68 0.76 28-32


alpha-D Glucose +112.2° => +52.7°
beta-D-Glucose + 18.7° => +52.7°

Stability of glucose and fructose.

Sugar pH of optimum stability

Glucose 4.0
Fructose 3.0
Stability is independent of temperature and concentration at these pH values.
Epimers - Differ at positions other than C1

   
   

C-2 epimer

 

C-4 epimer

Heptuloses 
 

Pentoses

   
         
   

Deoxysugars

   

Boat and Chair

 

Dissacharides are made up of two monosaccharides. The three most common are shown below:

Sucrose


Lactose




Maltose


Some oligosaccharides are of importance in foods such as:

Raffinose


Stachyose



Sucralose

Starch


Cellulose




 

 

 

 

 

 

 

 

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