BIOCHEM

LEC NOTES No. 3 CARBOHYDRATES

Monosaccharides
Fischer Projection formula open & linear structural formula of monosaccharides
C5 (the carbon atom next to a primary alcohol) is the basis in determining whether the
monosaccharide is in the D or L configuration
D isomer OH on the right
L isomer - OH on the left
a free carbonyl group gives the sugars its reducing property, i.e., these sugars are
reducing sugars & therefore will give positive results in all oxidizing tests
(e.g. siver mirror for Tollens, brick-red ppt. for Fehlings & Benedicts, yellow ppt. for
Phenylhydrazine test)
open structure of sugars gives a free carbonyl group & is only obtained if the sugar is
in aqueous solution
Aldohexose




Ketohexose

Haworth formula closed ring structure of monosaccharides
for an aldohexose, it is the hemiacetal formation between C1 (aldehyde functional
group) & C5 (alcohol functional group) to give the closed-hexagon ring structure

for a ketohexose, it is the hemiketal formation between C2 (ketone functional group) &
C5 (alcohol functional group) to give the closed-pentagon ring structure

closed-ring structures of sugars DO NOT give a free carbonyl group since there is a
C1-C5 oxide linkage for aldohexoses & a C2-C5 oxide linkage for ketohexoses,
therefore, NO REDUCING PROPERTY
in aqueous solutions, water hydrolyzes these oxide linkages, liberates the carbonyl
group & thus, these sugars become REDUCING SUGARS

Disaccharides

a glycosidic linkage is the bond that links two monosaccharide units

for maltose (glucose-glucose), it is the acetal formation between C1 of the 1st glucose
molecule and C4 of the 2nd glucose molecule therefore maltose has a 1,4-glycosidic
bond
maltose is a REDUCING SUGAR because even though C1 (from the 1st glucose mol) is
bound by both oxide & glycosidic bonds, C4 (from the the 2nd glu mol) is bound
only by an oxide linkage thus, in an aqueous solution,water can still hydrolyze this oxide
linkage & yield a free carbonyl group
for lactose (galactose-glucose), it is the acetal formation between C1 of the 1st galactose
molecule and C4 of the 2nd glucose molecule therefore lactose has a 1,4-glycosidic
bond
lactose is a REDUCING SUGAR because even though C1 (from the 1st gal mol) is bound by
both oxide & glycosidic bonds, C4 (from the the 2nd glu mol) is bound only by an oxide
linkage thus, in an aqueous solution,water can still hydrolyze this oxide linkage & yield
a free carbonyl group

for sucrose (glucose-fructose), it is the ketal formation between C1 of the 1st glucose
molecule and C2 of the 2nd fructose molecule therefore sucrose has a 1,2-glycosidic
bond
sucrose is the only NON REDUCING SUGAR because C1 (from the 1st glu mol) and C2
(from the the 2nd fru mol) are both bound by oxide & glycosidic linkages, therefore,
NO FREE CARBONYL GROUP
sucrose can give a false-positive result in an oxidation test if the 1,2-glycosidic bond
undergoes hydrolysis due to to prolong heating

Polysaccharides

starch a polymer of glucose

a starch granule has a hard, outer covering known as amylopectin (the branched 1,6-
glycosidic structure) & a soft inner layer, amylose (the linear 1,4-glycosidic structure)
uncooked, aqueous solution of starch gives a violet solution w/ I2 test (amylopectin)
and cooked or heated starch, gives a blue solution (amylose)
I2 Test (General Test for Starch)
Principle Involved: formation of starch-iodo complex
1) starch, being a polymer, traps the I2 in its helical structure giving a blue-colored
complex
2) on heating, the helical structure opens up, becomes linear & releases the iodine,
thus, solution turns colorless
3) on cooling, starch assumes the same helical structure & traps again the I2 molecule
(blue solution)

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HW 3 CARBOHYDRATES
1) a. Given the monosaccharide hemiacetal, identify the anomeric carbon (C1 C6) and
identify it as or anomer.

CH2OH
OH

O
OH

CH2OH

OH


b. How many chiral carbons are there?
c. Identify the carbons involved in forming the oxide linkage (C1 C6).
d. Give the physical state of the hemiacetal monosaccharide.
2) a. Given the monosaccharide hemiacetal, identify the anomeric carbon (C1 C6) and
identify it as or anomer.

CH2OH
OH

O OH
OH





OH

b. How many chiral carbons are there?
c. Identify the carbons involved in forming the oxide linkage (C1 C6).

 d. Give the physical state of the hemiacetal monosaccharide.

3) a. Is the disaccharide a reducing or a non-reducing sugar?
b. Which bond needs to be hydrolyzed for it to have a reducing property? (oxide or
glycosidic linkage)
c. Identify the carbons (C1 C6) involved in producing a free C=O group & in what
sugar unit (1st or 2nd structure)
CH2OH

CH2OH
O
O
H
O

O
OH
HO

OH
OH
HO
4) a. Is the disaccharide a reducing or a non-reducing sugar?
b. Which bond needs to be hydrolyzed for it to have a reducing property? (oxide or
glycosidic linkage)
c. Identify the carbons (C1 C6) involved in producing a free C=O group & in what
sugar unit (1st or 2nd structure)

CH2OH
O
HO

HO

HO

CH2OH
O O


CH2OH
HO
OH

5) a. If the two segments are to be joined to represent a fragment of a polysaccharide,
identify those carbons involved in forming this glycosidic bond (C1 C6).
b. Which bond is responsible for a (+) Fehlings test if it is going to be hydrolyzed?
(A or B)
A
CH2OH
CH2OH
CH2OH
CH2OH
O
O
O
O
HO
HO
O
O
OH
OH
HO
HO
OH
OH
OH
OH
HO
HO
B

Segment 1

Segment 2