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Carbohydrates
what we crave

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Carbohydrates
Carbohydrates - product of photosynthesis
- primary energy source for metabolic processes

Solar energy Inorganic CO2 O2

Organic carbon (carbohydrates)


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Carbohydrates
Carbohydrates - originally referred to hydrates of carbon
- the general formula of these compounds was CnH2nOn or Cn(H2O)n - polyhydroxyaldehydes and polyhydroxyketones and their derivatives

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Carbohydrates
Natural carbohydrates are subdivided into: - monosaccharides, or simple sugars containing three
to nine carbon atoms - polysaccharides, or polymers of monosaccharides - oligosaccharides, with two to ten monosaccharide units joined - disaccharrides.

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Properties of Carbohydrates
Nomenclature
carbohydrates are recognizable by an ose suffix. Ex. aldose, ketose roots referring to the number of carbon atoms are also used. Ex. pentose, hexose

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Properties of Carbohydrates
They contain one or more chiral carbons.
Chiral carbons are those that have four different groups, atoms or groups of atoms, attached to them. Carbohydrates are optically active.

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Properties of Carbohydrates
Fischer projections are useful in indicating the asymmetry around each of the chiral carbon atoms.

Relationship between the three dimensional structure and the Fischer projection.
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Properties of Carbohydrates
Enantiomers
Arrangement of groups around a chiral center. Nonsuperimposable mirror images Comprise of D/L pair D rotates polarized light to the right L rotates polarized light to the left

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Properties of Carbohydrates
They have multiple chiral centers.
there can be more than two stereoisomers number of stereoisomers is 2n

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Properties of Carbohydrates

Structure of D-glucose
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A Sweet Topic: Monosaccharides


Monosaccharides, or simple sugars
are an important class of biochemicals water soluble optically active D-glucose -> the most important

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A Sweet Topic: Monosaccharides


The most stable monosaccharide structures: Pyranose and furanose forms
Pyranose ring

2 possible structures:
Structure 1: Hydroxyl group on one carbon in the up position. Structure 2: Hydroxyl group on the corresponding carbon in the down position.
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A Sweet Topic: Monosaccharides


The two forms are known as anomers
Anomers are labeled as and
Haworth projections: pyranose structures of D-glucose

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A Sweet Topic: Monosaccharides


Mutarotation
Interconversion between the and forms
Furanose ring

Examples: ribose, fructose

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A Sweet Topic: Monosaccharides

Two forms of D-fructose


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A Sweet Topic: Monosaccharides


Derivatives of the monosaccharides
The reduction of the carbonyl group to an alcohol yields a reduced sugar (polyhydric alcohol).

D-ribose

D-ribitol

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A Sweet Topic: Monosaccharides


It is also possible to oxidize a monosaccharide to a carboxylic acid.

D-ribose

D-ribonic acid, an aldonic acid

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A Sweet Topic: Monosaccharides

D-ribose

D-ribouronic acid, a uronic acid

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A Sweet Topic: Monosaccharides


Monosaccharides, like all alcohols, may react with acids to form esters.

D-ribose-1-phosphate

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The most common monosaccharides


Dextrose glucose, or blood sugar Glucopyranose pyranose structure of dextrose Insulin hormone that controls the blood glucose level
Produced by the pancreas
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The most common monosaccharides


Fasting blood sugar 70-99 mg glucose/dL blood Blood sugar 2 hrs after meal 70-145 mg/dL American Diabetes Association
Blood glucose level associated to diabetes
126 mg/dL (fasting) 200 mg/dL (2 hrs after meal)

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The beginning of life: Ribose and Deoxyribose

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Sugar Joining Hands: Oligosaccharides


One or more glycoside linkages hold the monosaccharides together.

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Keeping it Simple: Disaccharides


Sucrose best-known disaccharide
Table sugar or cane sugar

Other important disaccharides


Maltose (malt sugar) Lactose (milk sugar)

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Keeping it Simple: Disaccharides

Maltose showing its (1-4) linkage


The loss of water molecule accompanies the formation of the linkage, which locks the left ring so that mutarotation is no longer possible.
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Keeping it Simple: Disaccharides

Lactose showing its (1-4) linkage

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Sucrose formed by joining -D-glucose and -D-fructose [(1-2)linkage]

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Keeping it Simple: Disaccharides


If the sweetness of sucrose is 100, then the sweetness level of glucose is 74, and that of fructose, 173. Fructose sweetest common sugar

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Keeping it Simple: Disaccharides


Artificial Sweetenerss
Saccharin (about 500 times as sweet as sucrose) Aspartame (200 times as sweet as sucrose) Sucralose (600 times as sweet as sucrose)
Splenda

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Starch and Cellulose: Polysaccharides


Starch is related to maltose and cellulose is related to lactose.

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Starch and Cellulose: Polysaccharides


Bread, pasta, and potatoes: Starches Starch polymer of -D-glucose Three common types:
Amylase (1-4) glucose Amylopectin -- (1-4) glucose linkages + (1-6) branches Glycogen animal starch
Similar to amylopectin with more branches

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Starch and Cellulose: Polysaccharides


Keeping the termites happy: Cellulose Cellulose similar to starch except that the linkages are (1-4) linkages
One of the most abundant biochemicals on earth

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Starch and Cellulose: Polysaccharides


Biological connective tissues: Acidic polysaccharides One of the major uses of polysaccharides in the body is the area of connective tissues
Tendons, ligaments, collagen

The repeating units of these polysaccharide derivatives are disaccharides


One component is amino sugar
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Biological connective tissues: Acidic polysaccharides

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Starch and Cellulose: Polysaccharides


Glycoproteins proteins with carbohydrates attached the linkage is by attachment to an asparagine, serine, or threonine residue

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