1) Draw both Fisher and Haworth formula of - D-glucose; mark all chiral carbons by * (3p)

Chiral carbons:
in D-glucose = C2, C3, C4, C5
in -D-glucose = C1, C2, C3, C4, C5
D-glucose -D-glucose

2) Draw the keto isomer of D-glucose and transform the compound to its L-isomer (= 2 formulas) (2p)

3) Write number of carbons found in: (6p)

galactose 6 sucrose 12
ribose 5 glucitol 6
glyceraldehyde 3 gluconic acid 6

4) Draw 2-epimer of -D-glucose (1p)

= -D-mannose

5) Add names of products of the reaction: (2p)

glucose + galactose lactose + water

6) Draw the structure formula of a glycerolphospholipid containing: palmitic acid, oleic acid and
amino ethanol as a base (charged polar group). Mark all ester bonds. (5p)

R1 = -(CH2)14-CH3
R2 = -(CH2)7-CH=CH-(CH2)7-CH3 /cis/

ester bonds: -O-CO- / -CO-O- / -O-PO- / -PO-O-

(2x between glycerol and fatty acid, 1x between glycerol
and phosphoric acid and 1x between phosphoric acid and
aminoethanol)
7) Draw the structure formula of isoprene. What is the name of its polymeric derivatives containing
30 carbons? (2p)

C30 = triterpene (= polymere of 6 isoprene molecules)

8) Draw the general structure of -L-amino acids: use both dissociated and undissociated form.
Mark -carbon. (3p)

9) Draw the tripeptide glutamyl-cysteinyl-glycine. Mark all chiral carbons and all peptide bonds.
What is the general name of a hydrolytic enzyme which can hydrolyze the tripeptide? (6p)

H2N-CH(R1)-CO-NH-CH(R2)-CO-NH-CH2-COOH 2 peptide bonds: -CO-NH-

R1 = -(CH2)2-COOH R2 = -CH2-SH C = chiral carbon

(Glu) (Cys)

Peptide bonds can be hydrolyzed by an enzyme called peptidase.

10) Explain the term denaturation of proteins (1p)

= the loss of secondary, tertiary and quaternary structures of a protein
(i.e. the loss of a spatial arrangement of a protein related to its native conformation
- a biological activity of the protein is also lost)

11) Draw the structure formula of a nucleotide containing adenine, ribose and two phosphates.
What is its name? Mark all hydrolyzable bonds and write their type (name).
Encircle a part of the molecule called nucleoside. (9p)

N-glycosidic bond between adenine and ribose

ester bond between ribose and phosphate
anhydride bond between two phosphates

nucleoside = adenosine: adenine + ribose