Carbohydrates Diagram

Carbohydrates

It is the most abundant organic compounds

chemical energy

Carbohydrates act as storehouses for (?)

Carbohydrates

(?) are supportive components in plants.

Carbohydrates

(?) are essential components of nucleic acids

Hydrate of Carbon

True or False? If false replace the underlined word to make the statement correct.

Carbohydrates means “Carbon of Hydrate”

True

True or False? If false replace the underlined word to make the statement correct.

Carbohydrates are rich in OH

Aldoses; Ketoses

What are the 2 major groups of Carbohydrates?

True

MAJOR GROUPS OF CARBOHYDRATES

True or False? If false replace the underlined word to make the statement correct.

Aldehyde —> Aldoses

Ketones —> Ketoses

Monosaccharides; Disaccharides; Oligosaccharides; Polysaccharides

Give the 4 classifications of Carbohydrates

Monosaccharides

Carbohydrates that cannot be hydrolyzed to a simpler compound.

Monosaccharides

General formula: CnH2nOn

-ose

The suffix “(?)” indicates that a molecule is a carbohydrate.

A

A.) Monosaccharides

B.) Disaccharides

C.) Oligosaccharides

D.) Polysaccharides

B

A.) Monosaccharides

B.) Disaccharides

C.) Oligosaccharides

D.) Polysaccharides

C

A.) Monosaccharides

B.) Disaccharides

C.) Oligosaccharides

D.) Polysaccharides

D

A.) Monosaccharides

B.) Disaccharides

C.) Oligosaccharides

D.) Polysaccharides

Aldoses

Monosaccharides containing the aldehyde group (-CHO)

Ketoses

Monosaccharides containing the ketone group (-C=O)

functional group; carbons; ose

NOMENCLATURE

Step 1: Identify the (?)

Step 2: Count the number of (?)

Step 3: Add the suffix (?)

Superimposable mirror images

(?) are images that coincide at all

points when the images are laid

upon each other

Nonsuperimposable mirror images

(?) are images where not all points coincide when the images are laid upon each other

not superimposable

True or False? If false replace the underlined word to make the statement correct.

“A person’s left and right hands are superimposable upon each other.”

Chiral

Nonsuperimposable on its mirror image

Achiral

Superimposable on its mirror image

True

True or False? If false, replace the underlined word to make the statement correct.

“If a molecule (or object) has a mirror plane or an inversion center, it cannot be chiral.”

plane of symmetry

How can you predict whether a given molecule is or is not chiral?

A molecule is not chiral if it has a (?).

Achiral

Chiral

Achiral

Chiral

If there is a prefix "trans", automatically it is (?)

asymmetric center

An (?) is an atom that is bonded to four different groups.

one

Organic molecules, especially monosaccharides, may contain more than (?) chiral center.

Fischer Projection

A two-dimensional representation for showing the configuration of tetrahedral stereocenters.

forward; rear

FISCHER PROJECTION

Horizontal lines represent bonds projecting (?) from the stereocenter.

Vertical lines represent bonds projecting to the (?).

plane

FISCHER PROJECTION

Only the stereo center is in the (?).

1891; Emil Fischer

In the year (?), (?) made the arbitrary assignments of D- and L- to the enantiomers of glyceraldehyde.

D-monosaccharide

The -OH on its penultimate carbon is on the right in a Fischer projection

L-monosaccharide

The -OH on its penultimate carbon is on the left in a Fischer projection.

Amino sugars

Contain an -NH2 group in place of an -OH group.

colorless; crystalline

PHYSICAL PROPERTIES

Monosaccharides are (?), (?) solids.

Ethanol

PHYSICAL PROPERTIES

Monosaccharides are slightly soluble to (?) and insoluble to nonpolar solvents such as diethyl ether, dichloromethane and benzene.

hemiacetals

Aldehydes and ketones react with alcohols to form (?).

Cyclic hemiacetals

(?) form readily when hydroxyl and carbonyl groups are part of the same molecule and their interaction can form a five- or six-membered ring.

Haworth Projections

A five- or six-membered cyclic hemiacetal is represented as a planar ring.

Anomeric carbon

HAWORTH PROJECTIONS

The new carbon stereocenter created in forming the cyclic structure is called the (?)

Anomers

HAWORTH PROJECTIONS

Stereoisomers that differ in configuration only at the anomeric carbon are called (?).

right; top

In a Haworth projection, the hemiacetal ring system is viewed “edge on” with the oxygen ring atom at the upper (?) (six- membered ring) or at the (?) (five- membered ring).

above; below

HAWORTH PROJECTIONS

In the D form, CH2OH is positioned (?) the ring.

In the L form, which is not usually encountered in biochemical systems, the terminal CH2OH group is positioned (?) the ring.

OH

HAWORTH PROJECTIONS

α or β configuration is determined by the position of the —(?) group on carbon 1 relative to the CH2OH group that determines D or L series.

same

HAWORTH PROJECTIONS

In β configuration, both —OH group and CH2OH group point in the (?) direction.

opposite

HAWORTH PROJECTIONS

In α configuration, both —OH group and CH2OH group point in (?) directions.

anomeric

CONVERTING FISCHER TO HAWORTH

Step 1: Draw a Haworth’s “stem”

Step 2: Number your atoms 1 through 5 starting from the (?) carbon and going clockwise

Step 3: If your sugar was D, then the carbon #6 is going to be looking “up” (down for the L sugar)

Step 4: The “right” groups on carbons 2, 3, and 4 in the Fischer projection go onto the “bottom” positions in Haworth

Step 5: The “left” groups on carbons 2, 3, and 4 in the Fischer projection go onto the “up” positions in Haworth

alpha-D-glucose; beta-D-glucose

What are the 2 forms of glucose?

Anomers

Cyclic monosaccharides that differ only in the position of the substituents on the anomeric carbon atom.

Pyranose

Cyclic monosaccharide containing a six-atom ring

Furanose

Cyclic monosaccharide containing a five-atom ring

cyclic hemiacetal

Aldopentoses also form (?)

furanoses

The most prevalent forms of D-ribose and other pentoses in the biological world are (?).

cyclic hemiacetal

D-Fructose also forms a 5-membered (?).

Strain-free chair conformation

For pyranoses, the six-membered ring is more accurately represented as a (?).

True

True or False? If false replace the underlined word to make the statement correct.

“In both Haworth projections and chair conformations, the orientations of groups on carbons 1- 5 of b-D-glucopyranose are up, down, up, down, and up and all are equatorial.”

up; down

CONVERTING HAWORTH TO CHAIR

The trick is to remember that just like the Haworth projections, the chair conformations also have the well-defined “(?)” and “(?)” positions!

Glucose

MONOSACCHARIDES

-Most abundant in nature

-Important in human nutrition

-6-membered cyclic form

Glucose

MONOSACCHARIDES

Other names:

—Grape sugar

—Blood sugar

—Dextrose

Galactose

MONOSACCHARIDES

-Used to differentiate between blood types

-6-membered cyclic form

Lactase

Which enzyme hydrolyzes β(1,4) glycosidic linkages?

Fructose

MONOSACCHARIDES

-Ketohexose

-High dietary sugar due to sweetness

-5-membered cyclic form

Fructose

Which monosaccharide is the sweetest tasting of all sugars?

Ribose

MONOSACCHARIDES

-Sugar in RNA

-Part of a variety of complex molecules which include:

RNA, ATP, DNA

-5-membered cyclic form

Disaccharides

Contain 2 sugar units; 2 monosaccharides joined by a glycosidic bond

Galactose

MONOSACCHARIDES

Other names:

—Brain sugar

—Milk sugar

Maltose

DISACCHARIDES

Glucose + Glucose

Units: α-D-glucose & β-D-glucose

Linkage: α(1,4) glycosidic linkage

Disaccharides

Two monosaccharides are joined by a glycosidic bond between the anomeric Carbon of one unit and an –OH group of the other unit.

A

2 Galactose

1 N-Acetyl-glucosamine

1 Fucose

A. Type O blood

B. Type A blood

C. Type B blood

Lactose

DISACCHARIDES

Glucose + Galactose

Units: β-D-galactose & α-D-glucose unit

Linkage: β(1,4) glycosidic linkage

Sucrose

Glucose + Fructose

Units: α-D-glucopyranose & β-D-fructofuranose

Linkage: α(1,2) glycosidic linkage

Sucrose

DISACCHARIDES

The most abundant of all disaccharides and found in plants. Also known as “table sugar”.

B

2 Galactose

1 N-Acetyl-glucosamine

1 Fucose

1 N-Acetyl-galactosamine

A. Type O blood

B. Type A blood

C. Type B blood

C

3 Galactose

1 N-Acetyl-glucosamine

1 Fucose

A. Type O blood

B. Type A blood

C. Type B blood

Cellobiose

DISACCHARIDES

Units: α-D-glucose, β-D-glucose

Linkage: β(1,4) glycosidic linkage

Polysaccharides

Polymers of many monosaccharide units bonded with glycosidic linkages.

Oligosaccharides

Carbohydrates that contain 3–10 monosaccharide units bonded to each other via glycosidic linkages.

Cellobiose

DISACCHARIDES

Cannot be digested by humans

Oligosaccharides

-Commonly found in onions, cabbage, broccoli, and whole wheat.

-Can distinguish blood types.

sweet; positive

Polysaccharides are not (?) and do not show (?) tests with Tollen’s and Benedict’s solutions,

whereas monosaccharides are sweet and show positive tests.

True

True or False? If false replace the underlined word to make the statement correct.

“Polysaccharides have limited water solubility.”

Storage polysaccharide

Polysaccharide that is a storage form for monosaccharides and used as an energy source in cells

Starches

POLYSACCHARIDES

Storage polysaccharide in plants

Glucose

POLYSACCHARIDES

(?) is the monomeric unit in starch

Amylose; Amylopectin

POLYSACCHARIDES

Give the two types of starch

Amylose

POLYSACCHARIDES

This type of starch is unbranched; α(1→4) glycosidic bonds

Amylopectin

POLYSACCHARIDES

This type of starch is branched; α(1→4) α(1→6) glycosidic bonds

B

POLYSACCHARIDES

Which glycosidic bond in Amylopectin causes the branching?

A. α(1→4) glycosidic bonds

B. α(1→6) glycosidic bonds

Glycogen

POLYSACCHARIDES

Storage polysaccharide in humans and animals

Glycogen

POLYSACCHARIDES

Branched chain polymer with α(1→4) glycosidic bonds in STRAIGHT chains and α(1,6) in BRANCHES

B

POLYSACCHARIDES

Which glycosidic bond in Glycogen causes the branching?

A. α(1→4) glycosidic bonds

B. α(1→6) glycosidic bonds

True

POLYSACCHARIDES

True or False? If false, replace the underlined word to make the statement correct.

“Glycogen contains only glucose units.”

do not

POLYSACCHARIDES

True or False? If false, replace the underlined word to make the statement correct.

“Humans do have enzymes that hydrolyze β(1,4) linkages.”

weaker

POLYSACCHARIDES

True or False? If false, replace the underlined word to make the statement correct.

“Chitin is stronger than Cellulose.”

B; A

Identify the type of structural notation for A and B

A. β(1,4)

B. α(1,4)