Carbohydrates
&
Nucleic Acids
Structure and Vocabulary
Fischer Projections
Classification
D and L Sugars based on
D- Glyceraldehyde
All D Sugars can be Degraded
to D-Glyceraldehyde
CHO
OH
CH2OH
Glyceraldehyde
CHO
OH
OH
CHO
HO
OH
CH2OH
thresose*
CH2OH
erythrose
CHO
OH
OH
OH
CHO
HO
OH
OH
CH2OH
Arabinose
OH HO
OH
OH HO
OH
OH
OH
OH HO
OH
OH
OH
OH
CH2OH
allose*
CH2OH
altrose
HO
HO
OH
OH
CH2OH
CH2OH
Xylose
CHO
CHO
OH HO
CHO
CHO
HO
CH2OH
Ribose
CHO
CHO
OH
HO
Lyxose*
CHO
CHO
OH HO
OH
OH HO
HO
HO
HO
HO
OH
CHO
CHO
OH HO
OH
OH
OH
CH2OH
CH2OH
CH2OH
CH2OH
CH2OH
CH2OH
glucose
mannose
gulose*
idose
galactose
talose
Threo and Erythro
Erythro & Threo each indicate a
pair of enantiomers
Epimers: Stereoisomers that Differ
at Only One Asymmetric Center
CHO
CHO
H
HO
HO
H
OH
H
H
OH
HO
H
H
HO
H
OH
OH
H
D & L sugars of the
CH2OH
same name are enantiomers
CH2OH
D-Galactose
L-Galactose
CHO
CHO
H
HO
HO
HO
OH
H
H
H
CH2OH
L-Altrose
a C-4 epimer of
D-Galactose
HO
H
H
H
OH
OH
H
OH
Inversion of only C-4 gives
an entirely different sugar
CH2OH
D-Altrose
a C-4 epimer of
L-Galactose
Pyranose Formation in Glucose
Pyranose forms of Glucose
O
H
HO
H
H
CH
OH
H
OH
OH
CH2OH
HO
HO
+
H , H2O
CH2OH
O
OH
HO
-D-glucopyranose
CH2OH
O
HO
HO
HO
OH
-D-glucopyranose
Glucose Anomers
 and 
O
1
2
H
3
HO
4
H
C
H
C
OH
C
H
C
OH
H
C
6
HO
OH HO
HO
HO
HO
HO
5
OH
-anomer
-anomer
CH2OH
6
CH2OH
5
4
OH
OH
O
1
3
OH
+
2
OH
H cyclizes to
pyranose form
CH2OH
O anomeric carbon
CH2OH
O OH
OH
H
OH
OH
-anomer
OH
-D-glucopyranose
-D-glucopyranose
D-Glucose
CH2OH
O
CH2OH
O
+
OH
OH
OH
-anomer
OH
Furanose Formation
-D-Fructofuranose
Evolution
of the
Pyranose
O
CH
H OH
HO H
HO
H
CH2OH
H
+
HO
H
OH
OH
-H
CH2OH
O
OH
O
H
CH2OH
D-Galactose
HO
OH
OH

+
+
CH2OH
HO
O OH
OH

OH
OH
OH
 and  D-Galactopyranose
Alkylation of Hemiacetal
Formation of Glycosides
CH2OH
O
OH
HO
HO
HO
-D-glucopyranose
CH2OH
O
HO
HO
HO
OH
-D-glucopyranose
HO
HO
CH3OH, H
+
CH2OH
O
OCH3
HO
methyl -D-glucopyranos ide
CH2OH
O
HO
HO
HO
OCH3
methyl -D-glucopyranos ide
CH2OH
O
OH
HO
HO
CH3OH, H
CH2OH
O
OH
HO
HO
-H
+
H
CH2OH
O
HO
HO
HO
HO
HO
methyl -D-glucopyranos ide
+
HO
-D-glucopyranose
HO
HO
+
CH2OH
O
OCH3
CH3OH
CH2OH
O
OCH3
HO
HO
HO
H
HOH
Protection of cis OH Groups with
Acetone - Acetonides
CH3
OH
OH
O
HO
O
CH3CCH3 , H3O
+
OH
O
CH3
O
O
OH
HO
+ H2O
OH
HO
O
CH3CCH3 , H3O
+
CH3
OH
O
CH3
O
O
O
O
CH3
CH3
+ H2O
Oxidize and Deprotect
CH3
CH3
OH
O
CH3
O
NaCr2O7, H2SO4
O
CH3
O
CO 2H
O
O
O
O
O
O
CH3
CH3
CH3
H3O
OH
+
CH3
CO 2H
O
HO
HO
OH
Maltose – a Disaccaharide
Naming a Disaccharide
from  D-mannose
OH
HO
HO
HO
HO
OH
CH2OH
O
O a  1-6' linkage
CH2
O
from  D-Allose
OH
6-O-(-D-mannopyranosyl)- -D-allopyranose
Sucrose – a Glucose-Fructose Dimer
Linkage of 2 Anomeric Centers
Splendid
OH
Cl
CH2OH
O
CH2OH
O
HO
HO
OH
CH2OH O
O
HO
CH2OH
HO
OH
CH2Cl
O
O
HO
CH2Cl
HO
Sucrose
Sucralose or Splenda
Cellulose – a Polymer of Glucose
CHO
H
HOCH2
OH
O
OH
OH
2-deoxy
OH H
CH2OH
D-2-deoxyribose
-D-2-deoxyribofuranose
OH
CH3
O P O
adenine
O
CH2
O
5
A nucleotide of DNA
N
4
1
3
O
O
O
2
H
P O
O
sugar
NH
thymine
O
Nucleotides of DNA
Base Pairing in DNA Helices
Double Helix
Replication
DNA Cross-linker
21
O
CH3O
O
O
O
O
N
CH3
OH
N
H
AcO
H
N
10
HO
Azinomycin B
Streptomyces sahachiroi
O
Prevents DNA from Unraveling
O
O
OH
OH
OH
OCH3 O
OH
O
CH3
NH2
Doxirubicin (adriamycin)
OH
Binds to DNA and inhibits enzyme topoisomerase II
DNA Strand