Carbohydrates Flashcards by Kyra Catedral

carbohydrate is a polyhydroxy aldehyde, a polyhydroxy ketone, or a compound that yields ________ or ________ upon hydrolysis.

polyhydroxy aldehydes
polyhydroxy ketones

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means “hydrate of carbon”

Carbohydrate

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Carbohydrates mean

means “hydrate of carbon”

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Carbohydrates contain

Carbon
Hydrogen
Oxygen

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Carbohydrates comes from the____ word “________” which means sugar

Latin

Saccharum

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Importance of carbohydrates

Source of energy

Storage form of energy

Precursors to many organic compounds

Participates in the structure of cell membrane and cellular functions

Used as drugs like antibiotics

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Classification of Carbohydrates

MONOSACCHARIDES
OLIGOSACCHARIDES
POLYSACCHARIDES

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are the simplest sugars

cannot be hydrolyzed further into smaller units

contains a single carbon chain

MONOSACCHARIDES

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MONOSACCHARIDES have __ to __ carbon atoms

3 to 9

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Monosaccharides that don’t end in -ose

2 trioses = glyceraldehyde & dihydroxyacetone

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CLASSIFICATION of MONOSACCHARIDES

• On the basis of number of carbons they posses
• ALDOSE or KETOSE depending upon their functional group

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A 6-carbon monosaccharide and has an aldehyde functional group is called

ALDOHEXOSE

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A 5-carbon monosaccharide with a ketone functional group is called =

KETOPENTOSE

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Carbonyl group

C=O

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ALL terminal groups of glucose (molecular formula), always ends with an_______ (e.g. СН2ОН)

alcohol

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second-to-the-last carbon) = called the

penultimate carbon

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Monosaccharides are classified on the number of C atoms.

Trioses

Pentoses

Hexoses

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T or P or H

Glyceraldehyde

Trioses (C3H6O3)

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M or P or S

Ribose

Pentose (C5H10O5)

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M or P or S

Deoxyribose

Pentose (C5H10O4)

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Pentoses C;H1o05

Examples

ribose, deoxyribose, ribulose

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Trioses example

Glyseraldehyde

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NADP

Nicotinamide
Adenine
Dinucleotide
Phosphate

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FAD

Flavin
Adenine
Dinucleotide

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HEXOSES Examples

Glucose Fructose Galactose (CH12O6)

• Needed to synthesize: Disaccharides Polysaccharides

Hexose

CLASSIFICATION OF FUNCTIONAL GROUP IN MONOSACCHARIDES

Aldehyde Keto

Aldehyde or Keto Glucose

Aldehyde

Aldehyde or Keto Fructose

Keto

STRUCTURE OF MONOSACCHARIDES

Fischer projection Haworth projection X-ray diffraction analysis

The straight chain structural formula

Fischer projection

Cyclic formula or ring structure

Haworth projection

Boat and chair form

X-ray diffraction analysis

Compounds possessing identical molecular formula but different structures =

isomers

Iso =

= "the same"

Types of Isomerism

Structural isomerism Steroisomerism

Type of isomerism in which compounds have the same molecular formula but differ in positioning

Structural Isomerism

Type of Isomerism in which • Differ in configuration • Presence of Asymmetric carbon (chiral carbon) atoms

Stereoisomerism

4 types of Stereoisomerism

D and L isomerism Optical isomerism Epimerism a and B anomerism

Chiral molecules that are mirror images of one another

Enantiomers

Has the -OH (hydroxyl) group on the RIGHT of its PENULTIMATE carbon

D-Monosaccharide

• Has the -OH (hydroxyl) group on the LEFT of its PENULTIMATE carbon

L-Monosaccharide

- second to the last carbon

PENULTIMATE CARBON

optically active compound is a compound that rotates the plane of polarized light. Presence of asymmetrical carbon atom causes optical activity

OPTICAL ISOMERISM

When a beam of plane polarized light is passed through a solution of carbohydrate, it will rotate the light to the RIGHT

Dextro-rotatory

When a beam of plane polarized light is passed through a solution of carbohydrate, it will rotate the light to the LEFT

Laevo-rotatory

• The stereoisomerism if 2 monosaccharides differ from each other in their configuration around a single specific carbon (other than the anomeric) atom.

EPIMERISM

- carbon derived from the carbonyl carbon of the open-chain form of the carbohydrate molecule

ANOMERIC CARBON

• Isomers obtained from the change of position of hydroxyl group attached to the anomeric carbon

ANOMERISM

-OH group at the anomeric, carbon is on the SAME side as the terminal CH2OH OH group = upward position

B (Beta)

OH group group at the anomeric carbon is on the side OPPOSITE from the terminal CH2OH OH group = downward position

a (Alpha)

HAWORTH PROJECTION (2)

Pyran Furan

• 6-membered hemiacetal ring

PYRAN

• 5-membered hemiketal ring

FURAN

MONOSACCHARIDES REACTION (2)

Oxidation to acidic sugars Reduction to sugar alcohol

MONOSACCHARIDES REACTION (4)

1. Weak oxidizing agent 2. Strong oxidizing agent 3. Enzymes 4. Reduction

Oxidizing agent used determines product

• to produce acidic sugars • To produce uronic acid

______ oxidizing agent Present in Tollens and Benedict's solution

Weak oxidizing agent

Weak oxidizing agent: Oxidizes the aldehyde end of an aldose)to give an - _________ The oxidation of the aldehyde end of glucose produces - _________ The oxidation of the aldehyde end of galactose) produces - _________

aldonic acid gluconic acid galactonic acid

- is a carbohydrate that gives a positive test in Tollens and Benedict's solution

Reducing sugar

Can oxidize both ends of the monosaccharide at the same time (carbonyl group & terminal primary alcohol group) to produce a dicarboxylic acid

Strong oxidizing agent

Can oxidize primary alcohol end of an aldose such as the D-glucose

Enzymes

Carbonyl group is reduced to a OH group using hydrogen as the reducing agent

Reduction to sugar alcohol

Reduction to sugar alcohol Glucose turns to

Glucitol

Carbonyl group present in a monosaccharide (either aldose or ketose), can be reduced to a hydroxyl group using hydrogen as the reducing agent

Reduction

For aldoses and ketoses, the product of the reduction is the corresponding polyhydroxy alcohol which is commonly known as

sugar alcohol

In a reduction reaction D-glucose becomes

D-glucitol

is an atom in a molecule that has four different groups tetrahedrally bonded to it.

chiral center

A molecule that contains a chiral center is said to be

chiral

molecule is a molecule whose mirror images are superimposable. molecules do not possess handedness.

achiral

The simplest example of a chiral monosaccharide molecule is the three-carbon monosaccharide called

glyceraldehyde

are isomers that have the same molecular and structural formulas but differ in the orientation of atoms in space.

Stereoisomers

are stereoisomers whose molecules are nonsuperimposable mirror images of each other, as in left-handed and right-handed forms of a molecule.

Enantiomers

are stereoisomers whose molecules are not mirror images of each other.

Diastereomers

is a two-dimensional structural notation for showing the spatial arrangement of groups about chiral centers in molecules.

Fischer projection formula

is a compound that rotates the plane of polarized light.

optically active compound

enantiomer that rotates plane-polarized light in a clockwise direction (to the right) is said to be

dextrorotatory

is a chiral compound that rotates the plane of polarized light in a counterclockwise direction.

levorotatory compound

Although there is no limit to the number of carbon atoms that can be present in a monosaccharide, only monosaccharides with____ to ____ carbon atoms are commonly found in nature.

three to seven

Monosaccharides are classiﬁed as _____ or _____ on the basis of type of carbonyl group

aldoses or ketoses

is a two-dimensional structural notation that speciﬁes the three-dimensional structure of a cyclic form of a monosaccharide.

Haworth projection formula