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Biological Macromolecules

This document provides information about common biological macromolecules and monosaccharides. It discusses the structures and properties of glucose, fructose, and galactose. Glucose is the most abundant monosaccharide and can form both alpha and beta cyclic structures. Fructose is a ketose and forms furanose and pyranose rings. Both glucose and fructose undergo cyclization to form hemiacetals. The document also briefly mentions ribose and deoxyribose which are pentoses involved in DNA and RNA synthesis.

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186 views39 pages

Biological Macromolecules

This document provides information about common biological macromolecules and monosaccharides. It discusses the structures and properties of glucose, fructose, and galactose. Glucose is the most abundant monosaccharide and can form both alpha and beta cyclic structures. Fructose is a ketose and forms furanose and pyranose rings. Both glucose and fructose undergo cyclization to form hemiacetals. The document also briefly mentions ribose and deoxyribose which are pentoses involved in DNA and RNA synthesis.

Uploaded by

api-337296800
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Biological

Macromolecules
Carbohydrates
Protein
Lipids
Nucleic Acids

Monosaccharides:
Structure and
Nomenclature
Glucose
Galactose
Fructose

CH2OH

H
C O
H
H C OH

OH

OH

OH

CH2OH

CH
2OH
Nomenclature

Based on the number of


carbon Atoms

Based on the Functional Group


Aldoses (e.g., glucose)
have
an
aldehyde
group at one end.
H

Ketoses (e.g., fructose)


have a keto group,
usually at C2.

CH2OH
C

HO

OH

OH

OH

OH

OH

HO

CH2OH

CH2OH

D-glucose

D-fructose

OH

OH

CH2OH

CH2OH
C

OH

OH

OH

CH2OH

H
C

OH

OH

OH

CH2OH

CH2OH

OH

OH

CH2OH

Stereoisomers

Chiral Carbon Atoms

Enantiomers
The enantiomer that rotates
polarized light to the left is
the
levorotatory
or
(-)
enantiomer.
The enantiomer that rotates
it to the right is the
dextrorotatory
or
(+)
enantiomer.

Fischer projections
Fischer projections depict
three-dimensional
shapes
for chiral molecules, with
the
chiral
carbon
represented
by
the
intersection of two lines.
D and L - Configurations

Fischer projections

CH2OH

H
C O
H
H C OH

OH

OH

OH

CH2OH

D- and LCH
2OH
Configuration

D vs. L - Configuration
O

C
H C OH
HO C H
H C OH
H C OH
CH2OH
D-glucose

C
HO C H
H C OH
HO C H
HO C H
CH2OH
L-glucose

Glyceraldehyde

CHO
C O
H
OH C H
CH2OH

CHO
C O
H
H C OH
CH2OH

CH2O
H
C O

H C O
H
O
C H
H
H C O
H
H C O
CH2H
O

H C O
H
O
C H
H
H C O
H
O
C H
H
CH2O

H
C

Indicate whether each


of the following
molecules is an
aldose or ketone?
L or D configuration?

CH3
C
H C

O
OH

CH2OH

CH2O
H
C O
O
C
H
H C

H
H

H C O
H
CH2O

H
C O
H C OH
CH2OH

H
C

OH C

OH C

OH
H

CH2OH

CH3
C

H C

OH

OH

H C O
H
CH2O

Glucose
the
most
common
carbohydrate and classified
as a monosaccharide,
an aldose,
a hexose,
reducing sugar.
It is also known as dextrose
Immediate source of energy

Hemiacetal &
Hemiketal
An aldehyde can react with an
alcohol to form a hemiacetal.
A ketone can react with an
alcohol to form a hemiketal.

Hemiacetal and
Hemiketal
H
C

R'

OH

R'

OH

aldehyde

alcohol

hemiacetal

R
C

R
O

"R

OH

R'

ketone

"R

C
R'

alcohol

hemiketal

OH

Cyclization of Glucose

Glucose
forms
an
intramolecular hemiacetal, as the
C1 aldehyde & C5 OH react,
to
form a 6-member
pyranose ring (six-membered
ring containing an oxygen
atom)
named after pyran
These representations of the

Cyclization of Glucose
Cyclization of glucose produces a
new asymmetric center at C1. The
2
stereoisomers
are
called
anomers, & .
Haworth projections represent
the cyclic sugars as having
essentially planar rings, with the
OH at the anomeric C1:
a (OH below the ring)
(OH above the ring).

Cyclization of
Glucose CHO
1

H
HO
H
H

2
3
4
5
6

OH

D-glucose

OH

(linear form)

OH

CH2OH
6 CH2OH

6 CH2OH
5

H
4

OH

H
OH
3

OH

-D-glucose

OH

H
4

OH

H
OH
3

OH

OH

-D-glucose

Anomers of Glucose
6 CH2OH

6 CH2OH
5

H
4

OH

H
OH
3

H
2

OH

-D-glucose

H
1

OH

H
4

OH

H
OH

OH

OH

-D-glucose

Fructose
Also called levulose and fruit
sugar
Sweetest of all sugar
A ketose
Main source of energy for the
spermatozoa

Cyclization of Fructose

Cyclization of Fructose

Pyranose vs. Furanose

Galactose

Galactose is classified as a:
monosaccharide,
an aldose,
a hexose,
reducing sugar.
Found in milk

Galactose

Pentoses
Ribose and Deoxyribose
Pentoses
Used in the synthesis
of DNA and RNA

Ribose and
Deoxyribose

End!!!!!!

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