CARBOHYDRATE CHEMISTRY

1. STEREOISOMERS - Cpds. with the same

formula and attachment of atoms but with different
arrangements of the atoms in space.
2. ENANTIOMERS Stereoisomers in which one
isomer is the non-superimposable mirror image of
the other.
o Configuration is determined by: position of the
OH on the highest number asymmetric carbon
Least oxidized carbon: a Carbon linked to four
different atoms farthest from the carbonyl carbon
o L configuration: if OH on Left
o D configuration: if OH on Right;
cells prefer this configuration
3. CHIRALITY- The C molecule has 4
different substrates attached to it
-TETRAHEDRAL CARBON/CHIRAL
CENTER
- They are NON SUPERIMPOSABLE
- GLYCERALDEHYDE: most studied carbon
4. CARBONYL CARBON
- A carbon that is double bonded with O2 in a
fischer/open formula
- Most oxidized carbon
5. EPIMER- Stereoismers which differ in the
arrangement of substituents in ONLY ONE
POSITION.
Epimerase enzyme responsible for
interconversion of epimers
- In monosaccharide epimers, the position of
OH distinguishes the monosaccharide. The
carboxyl group remains the same.

FISCHER PROJECTION
FORMULA
Linear formula which can
be depicted in the D- or
L-form

D-Glucose and D-Mannose epimers at C2

ALDEHYDE

KETONES

Molecule wherein
the carbonyl carbon
number 1 binds with
oxygen
R Group is a
HYDROGEN atom

Molecule wherein the

carbonyl carbon number 2
binds with oxygen

React with an
alcohol to form a
HEMIACETAL

Counting of Carbons
starts from the topmost
carbon going down.
The topmost carbon is
thus labeled Carbon 1
or C1 or Position 1

R Group is another
HYDROXYMETHYL group
When Aldehyde group
tautomerizes into a keto
group
React with an alcohol to
form a HEMIKETAL
OH on RIGHT : DEXTER
OH on LEFT: LEVO

HAWORTH
FORMULA
The cyclic form of the
Fischer formula that
can be depicted in the
or form.
Locate the oxygen in
the ring. The Carbon
on either side of the
oxygen. The carbon
with the attached
OH group is the
Anomeric Carbon

: OH group is axial
DOWN
: OH group is axial
UP

Furanose 5 membered ring (Fructose)

Pyranose 6-membered ring (Glucose)
MOST STABLE
ANOMERS isomeric forms of monosaccharides
that differ only about the hemiacetal/hemiketal C.

BIOLOGICALLY IMPORTANT CARBOHYDRATES: MONOSACCHARIDES simple sugars; ALL ARE REDUCING SUGARS
Carbohydrates that cannot be hydrolyzed into simpler compounds
GLUCOSE
GALACTOSE
MANNOSE
ALDOHEXOSE - Monosaccharide that has both analdehyde (aldose) and six carbons (hexose)
Pyran-D is the most stable form of glucose
Empirical formula
Differs with Glucose in the position of OH
Differs with
(C6-H12-O6)
at C4 (Non-reducing end)
Glucose in the
Chief source of energy
Can be changed to glucose in the liver and
OH configuration
for living organisms
metabolized.
at C2.
Most important
- Synthesized in the mammary glands to
- A constituent of
Monosaccharide.
make the lactose of milk.
many
Sugar of the body.
Less soluble and less sweet compared to
glycoproteins
Occurs naturally in the
glucose
D-configuration vs.
- A constituent of glycolipids and
L-configuration
glycoproteins.

FRUCTOSE
Ketopentose
(5 - Carbon ring)
Isomer of 3 aldohexose
Differs in Glucose in C1
and C2
Can be changed to
GLUCOSE in the liver
Furan Ring
-C1 and C6 are outside
the ring and susceptible
to nucleophilic attack.

RIBOSE
Aldopentose

DEOXYRIBOSE

Structural elements of nucleic

acids and coenzymes, e.g. ATP,
NAD, NADP, Flavoproteins.
RNA
DNA
Intermediates
in the HMP
Shunt.
C2 in ribose is
OH

In deoxyribose,
C2 reduced to H

BIOLOGICALLY IMPORTANT CARBOHYDRATES: DISACCHARIDES formed when anomeric carbon of a sugar molecule interacts
with one of several hydroxyl groups in other sugar molecules
st
nd
Bonded by glycosidic bonds: GLYCOSIDIC BOND FORMATION Covalent bond join a CHO molecule (Anomeric C of 1 molecule and C4 of 2 molecule)
MALTOSE
1,4 glycosidic bond linkage
-D-glucose + -D-glucose
broken down by MALTASE
linear

ISOMALTOSE
1,6 glycosidic bond linkage
-D-glucose + -D-glucose
broken down by
SUCRASE-ISOMALTASE COMPLEX
branched

Reducing sugar

LACTOSE
1,4 glycosidic bond linkage
-D-galactose +-D-glucose
broken down by
LACTASE, -GALACTOSIDASE
Lactose intolerance
indigestion of lactose-richfoods
caused by depletion of enzymes
lactase or - galactosidase

SUCROSE
1- 2 glycosidic bond linkage
-D-glucose + -D-fructose
broken down by SUCRASE
*synthesized only in plants *commonly known as
table sugar
Non-reducing sugar

BIOLOGICALLY IMPORTANT CARBOHYDRATES: POLYSACCHARIDES - long polymers of oligosaccharides formed via glycosidic linkages, which could either
be linear or highly branched, by multiple monosaccharides
- OLIGOSACCHARIDES: contain 3-4 monosaccharide connected through glycosidic bonds
- Functions: o Energy storage (Amylose, Glycogen) o Structural integrity maintenance (Cellulose)
- Types of Polysaccharides:
o Homoglycan/homopolymer/homopoly saccharide a long polymer of one type of monosaccharide, such as Starch
o Heteroglycan/heteropolymer/heteropo lysaccharide a long polymer consisting of more than one type of monosaccharide
STARCH
a long polymer of glucose synthesized by plants for energy storage,
found in potatoes, legumes, and other vegetables
Its digestion begins in the mouth through - amylase, which produces an
intermediate called -dextrins, an oligosaccharide containing -1,6
glycosidic bonds and -1,4 glycosidic bonds.
Two main constituents of
starch:
o Amylose an unbranched
(linear) chain of glucose
residues connected by -1,4
linkages. Involved in glucose
storage in plants.
o Amylopectin - branched
version of amylose containing
both an -1,4 linkages and 1,6 linkages, which allows for
branching.
- Both constituents are rapidly
hydrolyzed by salivary and
pancreatic -amylase

CELLULOSE
A long polymer of glucose with - 1,4
linkages synthesized by plants to serve
a structural role; found in the cell wall of
plants
Its linkage makes it insoluble since no
enzyme in the human body is able to
break glycosidic bonds.

GLYCOGEN
a long polymer of glucose with one -1,6
linkage for 8-12 -1,4 linkages
synthesized by animal cells for energy
storage
Highly branched and compac than
amylopectin.