Documente Academic
Documente Profesional
Documente Cultură
Carbohydrate
Human Biochemistry
HCD 12103
Properties of monosaccharide
Recognize by ose suffix
Eg: aldose a monosaccharide where
the carbonyl group is aldehyde
Eg: ketose a monosaccharide where
the carbonyl group is ketone
Sub-classified by number of carbons:
i.e. tri (3), tetr- (4), pent-(5),.
Flash back..
Carbonyl group: O
C
A
aldehyde: O
ketone:
C
H
Classification of
Monosaccharides
Aldohexose (e.g., glucose)
have an aldehyde group at
one end.
H
H
HO
H
H
C
C
C
C
C
C H 2O H
C
OH
H
OH
OH
C H 2O H
HO
OH
OH
C H 2O H
LEARNING CHECK
Determine if there is a chiral carbon in
each compound
CI
CI
CH3
CH3
CH2CH3
Stereoisomer
Stereoisomer
isomeric molecules that have the
same molecular formula and
sequence of bonded atoms, but differ
only in the 3-D orientations of their
atoms in space
DO NOT confuse with structural
isomer
Stereoisomer
Can be devided into
enantiomer, diastereomer
and epimer
Enantiomer
2 stereoisomers that
related to each other by a
reflection: they are mirror
image, non-superimposable
Enantiomers
Enantiomers
Enantiomer
(mirror
image
s
isomers)
Enantiomers
Important properties of
enantiomers
Same physical properties (melting
point, boiling point, etc. except
the interaction with polarized
light.
Same chemical properties except
when another chiral molecule is
involved.
FISCHER PROJECTIONS
Represent mirror images (enantiomers)
in two dimension.
Place the carbonyl group at or near the
top and the last achiral CH 2OH at the
bottom.
If hydroxyl (OH) on highest numbered
chiral carbon
to the right - D-isomer
to the left L-isomer
Most naturally occurring sugars are
D isomers
FISCHER PROJECTIONS
Diastereomers
Stereoisomer not related
through a reflection
operation.
Not mirror image of each
other
A pair of
enantiomers
Important properties of
diastereomers
Different physical properties.
Different chemical / biological
properties.
Epimers
Diastereomers that differ the
configuration at single asymmetric
carbon atom.
D-glucose
D-galactose
Hemiacetal formation
An aldehyde can react with an
alcohol to form a hemiacetal.
Hemiketal formation
A ketone can react with an
alcohol
to form a hemiketal.
Haworth Projection
A way of representing a cyclic (closed
chain) carbohydrate.
Haworth Projection
Furanose
form
Pyranose
form
Haworth projection
Mutarotation
The and anomers interconvert in
solution by maturation.
This process requires that the ring
structure open to the linear form
during the interconversion.
Mutarotation
Chemical properties of
monosaccharide
Many aldoses are reducing sugar (reducing
agent)
Test for reducing sugarFehlings or
Benedicts solution, to check glucose in
urine of diabetic
Monosaccharide + methanol + HCl
glycosidic bond
Once glycoside forms, the ring is locked,
will not reopenno mutarotation
Monosaccharide
derivatives
D-Gluconic acid
D-Glucuronic acid
D-Glucaric acid
Keeping it
simple:disaccharides
Consist of 2 monosaccharides bonded
together.
Lactose, sucrose, maltose
Contain glycosidic bond
Notice that
each
disaccharide
has at least 1
glucose
molecules
Formation of lactose
Formation of sucrose
Formation of raffinose
3 unit of monosaccharide
Formation of Stachyose
4 unit of monosaccharide
Starch and
Cellulose:Polysaccharide
2 most important polysaccharide are
starch and cellulose
Both are D-glucose polymers
Difference:linkages between glucose
units
Starchmaltose
Celluloselactose
Biological connective
tissue:Acidic polysaccharides
CT holds our parts together
Includes tendons, ligaments and
collagen
One of component of polymer is
amino sugar
Examples: hyaluronate and heparin
glycoprotein
Most proteins occuring in blood serum
are glycoproteins
Protein + carbohydrate glycoprotein
In general, linkage is by attachment to
asparagine, serine or threonine
residue.
Appear in some soluble proteins and
membrane proteins.