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149 Cards in this Set

  • Front
  • Back

Carbohydrates

Most abundant organic compounds in the plant world

"Hydrates of Carbon"

Other term of Carbohydrates

Cellulose

Carbohydrates in plants

Chitin

Carbohydrates in Crustacean Shells

Acidic Polysaccharides

Carbohydrates of the components of connective tissues in animals

D-ribose & 2-deoxy-D-ribose

Carbohydrates of Nucleic Acids

Carbohydrates

They originate as products of photosynthesis

Photosynthesis

Endothermic reductive condensation of carbon dioxide requiring light energy and the pigment chlorophyll

Cn(H2O)m

Carbohydrates is derived from this formula

Hemiacetal

Hemiacetal Functional Group

Aldehyde Functional Group

Ketone Functional Group

Carbonyl Group

Saccharides

Simpler members of the CHO family

Saccharum

Latin word for sugar

Glucose, Galactose, Fructose, Xylose

(4) Common Monosaccharides

Glucose & Galactose

Monosaccharides that are aldoses

Glucose, Galactose, Fructose

(3) Monosaccharides that are hexoses

Fructose

(1) example of a ketose monosaccharide

Xylose

An example of common pentose monosaccharide

Sucrose, Lactose, Maltose

(3) Examples of Disaccharides

Sucrose

Glucose + Fructose

Lactose

Glucose + Galactose

Maltose

Glucose + Glucose

Amylose & Amylopectin (Starch)


Glycogen & Cellulose (Non-Starch)

(4) Common Polysaccharides

Monosaccharides

Contains a single polyhydroxy aldehyde or polyhydroxy ketone unit

Disaccharide

Contains two monosaccharides units covalently bonded to each other

Oligosaccharides

Contains two to ten monosaccharide units covalently bonded to each other

Polysaccharide

Contains many monosaccharide units covalently bonded to each other

Acetal

A functional group that has (2) -OR groups

Hemiacetal

A functional group that has (1) -OR group and (1) -OH group

Acetal

A functional group that can be converted into aldehyde / ketone

"-ose"

Suffix that indicates that a molecule is a carbohydrate

Hexose

Six - carbon monosaccharide

Pentose

Five - carbon monosaccharide

Aldose

Monosaccharide containing an aldehyde group

Ketose

Monosaccharides containing a ketone group

"-ulose"

A suffix that indicates that it is a ketose

Trioses

Smallest Monosaccharides

Aldotriose Glyceraldehyde


Ketotriose Dihydroxyacetone

What are the (2) trioses?

D-Glyceraldehyde

Dihydroxyacetone

Fischer Projection

Two-dimensional representation to show the configuration of carbohydrates

2,3-dihydroxypropanal

IUPAC name for Glyceraldehyde

1,3-dihydroxypropanone

IUPAC name for Dihydroxyacetone

Emil Fischer

Who proposed the D,L system

1891

When did Emil Fischer proposed the D,L system?

Enantiomer

One of two stereoisomers that are non-superimposable complete mirror images of each other

Chiral center farthest from the carbonyl group (Penultimate Carbon)

What is the reference point in a D- or L- Monosaccharide?

Penultimate Carbon

Chiral center that is always next to the last carbon on the chain

D-Monosaccharide (Dextrorotatory)

A monosaccharide that has -OH group on its penultimate carbon to the right

L-Monosaccharide (Levorotatory)

A monosaccharide that has the -OH group on its penultimate carbon to the left

D-glucose, D-galactose, D-fructose

Most abundant hexoses (3)

Glucose

Most common hexose

Glucose

"Dextrose"

Glucose

"Grape Sugar"

Glucose

"Blood Sugar"

Glucose

Synthesized in Photosynthesis (by chlorophyll-containing plants using sunlight as a source of energy)

1) Carbon Dioxide


2) Water


3) Energy/Sunlight


4) Chlorophyll


5) Glucose


6) Oxygen

What are the (6) ingredients of Photosynthesis?

D-fructose

D-Glucose

D-Galactose

Sucrose

"Table Sugar"

Lactose

"Milk Sugar"

D-ribose

Monosaccharide in RNA

2-deoxy-D-ribose

Monosaccharide in DNA

Ketotriose (Triuloses)

What kind of Aldose or Ketose is Dihydroxyacetone?

Ketotetrose (Tetruloses)

What kind of Aldose or Ketose is D-erythrulose?

Ketopentoses (Pentuloses)

What kind of Aldose or Ketose is D-ribulose?

Ketopentoses (Pentuloses)

What kind of Aldose or Ketose is D-xylulose?

Ketohexoses (Hexuloses)

What kind of Aldose or Ketose is D-psicose?

Ketohexoses (Hexuloses)

What kind of Aldose or Ketose is D-fructose?

Ketohexoses (Hexuloses)

What kind of Aldose or Ketose is D-sorbose?

Ketohexoses (Hexuloses)

What kind of Aldose or Ketose is D-tagatose?

Haworth Projection

Two-dimensional structural notation that specifies the three-dimensional structure of a cyclic monosaccharide

Position of the terminal CH2OH group on the highest-number ring carbon atom

In Haworth Projection, where is the D or L form of a monosaccharide determined?

Above the Ring

In Haworth Projection, where is the terminal CH2OH positioned in a D-Monosaccharide?

Below the ring

In Haworth Projection, where is the terminal CH2OH positioned in a L-Monosaccharide?

alpha or beta configuration

It is determined by the position of the -OH group on carbon 1 relative to the CH2OH group that determines the D or L series

Beta-Monosaccharide

A monosaccharide that the -OH on the anomeric carbon lies on the same side of the ring as the terminal -CH2OH

Alpha-Monosaccharide

A Monosaccharide that the -OH on the anomeric carbon lies on the side of the ring opposite from the terminal -CH2OH

Amino Sugars

A monosaccharide in which an -OH group is replaced by an -NH2 group

D-Galactosamine

D-Mannosamine

D-Glucosamine

N-Acetyl-D-Glucosamine

Derivative of D-Glucosamine

D-Glucosamine

An Amino Sugar that is a component of many polysaccharides including chitin

Colorless, Crystalline Solids, Sweet to the Taste

Color, Type of Matter and Taste of Monosaccharides

Soluble in Polar (Water)


Insoluble in Non Polar (Slightly Soluble in Ethanol)

Solubility of Monosaccharides

Hemiacetals

Formed when the aldehydes or ketones react with alcohols

Furanose (-Furan)

5-membered ring

-Pyran (Pyranose)

6-membered ring

Acetal

Yields when hemiacetal is treated with one molecule of alcohol

Glycoside

A carbohydrate in which the -OH group on its anomeric carbon is replace by an -OR group

Glycosidic Bond

A bond form between the hydroxyl group of a carbohydrate with the hydroxyl group of another carbohydrate

Glycosidic Bond

Bond from the anomeric carbon of a glycoside to an -OR group

Glycosidic Bond

Can be N-linked or O-linked

Reduction to Alditiols

Carbonyl group is reduced to an hydroxyl group by a variety of reducing agents, including hydrogen in the presence of a transition metal catalyst and sodium borohydride - alditols

Xylitol

Used as a sweetening agent in sugarless products

Sorbitol

D-Mannitol

Erythritol

Oxidation to Aldonic Acids (Reducing Sugars)

Aldehyde group of an aldose can be oxidized, under basic conditions, to a carboxylate group

Oxidation to Uronic Acids

Enzyme-catalyzed oxidation of the primary alcohol at carbon 6 of a hexose yields a uronic acid

Phosphoric Esters

Important in the metabolism of Monosaccharides

Sucrose

Most abundant Disaccharides

Sucrose

Obtained principally from the juice of sugar cane and sugar beets

Alpha-1,2-glycosidic bond

Bond between carbon 1 of alpha-D-glucopyranose and carbon 2 of beta-D-fructofuranose in sucrose

Lactose

Principal sugar present in milk

Beta-1,4-glycosidic bond

Bond between D-galactopyranose and carbon 4 of D-glucopyranose

Maltose

Derive its name from the juice of sprouted barley and other cereal grains

Maltose

Consist of 2 units of D-glucopyranose joined by a glycosidic acid between carbon 1 of one unit and carbon 4 of the other unit

Sucrose

A disaccharide that has no isomers

Lactose and Maltose

(2) disaccharides that contains a hemiacetal group and can exist in alpha and beta anomeric forms

Fructose

Sweetest Sugar

Lactose

A sugar that has almost no sweetness and is sometimes added to food as filler

Starch (Amylose and Amylopectin)

Used for energy storage in plants

Starch (Amylose and Amylopectin)

Its complete hydrolysis yields only D-Glucose

Amylose

Composed of continuous, unbranched chains of as many as 4000 D-glucose units joined by alpha-1,4-glycosidic bonds

Amylopectin

Contains chains of as many as 10,000 D-glucose units joined by alpha-1,4-glycosidic bonds and branched by new chains of 24-30 units at alpha-1,6-glycosidic bonds

Amylose

Makes up about 20% of starch

Glycogen

Acts as the energy-reserve carbohydrate for animals

Chitin

Second most abundant sugar

Chitin

Gives rigidity to the exoskeleton of crabs, lobsters, shrimp, insects and other arthropods

Chitin

Found in the cell walls of fungi

Chitin

Contain both glycosidic linkages and amine bonds - can be broken down by hydrolysis

N-acetyl-D-Glucosamine

Monosaccharide of Chitin

Chitin

Heparin

Highly-sulfated polysaccharide with only 15-90 disaccharide residues per chain

15-90 Residues

How many disaccharide residues does heparin have?

D-glucuronate-2-sulfate

Sulfate-derivative of D-glucuronate

N-Sulfo-D-Glucosamine-6-Sulfate

Doubly sulfated derivative of D-Glucosamine

1) D-Glucuronate-2-sulfate


2) N-sulfo-D-Glucosamine-6-sulfate

(2) Monosaccharides of Heparin

Hyaluronic Acid

Contains alternating residues of N-acetyl-Beta-D-Glucosamine and D-Glucoronate

1) N-Acetyl-Beta-D-Glucosamine


2) D-Gluconate

(2) Monosaccharides of Hyaluronic Acid

Hyaluronic Acid

Product when the CH2OH group of glucose is oxidized to a -COOH group

Hyaluronic Acid

C6H12O6

Formula of Monosaccharides

C12H22O11

Formula of Disaccharides

Glycogen

Carbohydrate storage that provides a short-term energy reserve

16

Relative Sweetness of Lactose

32.1

Relative Sweetness of Galactose

32.1

Relative Sweetness of Galactose

32.5

Relative Sweetness of Maltose

74.3

Relative Sweetness of Glucose

100

Relative Sweetness of Sucrose

173

Relative Sweetness of Fructose

Muscle and Liver

Where is the Glycogen stored? (2)

Cellulose

Non-digestible Carbohydrate