Lecture 9

Lecture 9
ЦифроваяIN 3D-медицина
INTRODUCTION Заголовок CARBOHYDRATES:
structure, functions, digestion
Результаты в области компьютерной графики и геометрического
Подзаголовок презентации
моделирования
Dr. Elena O. Polovinkina

2021
Carbohydrates (saccharides, sugars)
Cx(H2O)y
Carbohydrates are defined as «polyhydroxy aldehydes, polyhydroxy ketones, or
substances that give such compounds on hydrolysis».
Carbohydrates
monosaccharides oligosaccharides polysaccharides

Monosaccharides
are polyhydroxy carbonyl compounds: polyhydroxy aldehydes or polyhydroxy ketones.
Depending on According to
the functional the number
group of C
trioses
(C3)
aldoses ketoses tetroses

(C4)
pentoses
(C5)
hexoses
(C6)
ribose glucose mannose fructose heptoses

(C7)
is neither diastereomer nor enantiomer
but constitutional isomers
Three ways to represent the two
enantiomers of glyceraldehyde
a molecule with n chiral centers can have 2n stereoisomers
If the chiral carbon farthest from the carbonyl

group has hydroxyl on the right, a compound
is a D monosaccharide and visa-versa.
Designations D and L refer only to the
configuration of the highest numbered (or the
lowest in the Fischer projection) chiral
carbon. They are not used for other chiral
centres.
The family of the D-aldoses with up to
six carbon atoms
Two stereoisomers that differ in
configuration at only one chiral centre
are called epimers
diastereomers but not

enantiomers
Formation of hemiacetals and hemiketals
An aldehyde
or ketone can react with an
alcohol in a 1:1 ratio to yield a
hemiacetal or hemiketal, creating
a new chiral center at the carbonyl
carbon.
Substitution of a second alcohol
molecule produces an acetal or
ketal.
When the second alcohol is part of
another sugar molecule, the bond
produced is a glycosidic bond
Formation of the two cyclic forms
of D-glucose
Reaction between the aldehyde group at

C-1 and the hydroxyl group at C-5 forms
a hemiacetal linkage, producing either
of two stereoisomers, the α and β
anomers, which differ only in the
stereochemistry around the
hemiacetal carbon.
anomeric carbon Isomeric forms of

monosaccharides that differ
only in their configuration
about the hemiacetal or
hemiketal carbon atom are
called anomers.
Anomers
The designation α indicates that the hydroxyl group at the anomeric center is on the s
side as the hydroxyl attached at the farthest chiral center,
whereas the designation β indicates that these hydroxyl groups are on opposite sides.
A tautomeric equilibrium of D-glucose
mutarotation
The Haworth formulas vs
the Fischer projection
Radicals at the right Radicals below the ring plane
The Fischer projection The Haworth formula

Non-classical sugars
Deoxy sugars - the absence of a hydroxyl group (or groups);

Amino sugars - replacement of an OH group (or groups) by the NH2 and
their N-acetylated derivatives group or -NHCOCH3 group;
Uronic acids - the atom C-6 is oxidized to a carboxyl group;
Aldonic acids - the atom C-1 is oxidized to a carboxyl group;
Aldaric acids - both C-1 and C-6 are oxidized to carboxyl groups;
Alditols - a carbonyl group is reduced to an alcoholic group.
Some hexose derivatives important
in biology
Formation of maltose
O-glycosidic bond
Rules of naming oligosaccharides
the name describes the compound written

with its nonreducing end to the left:
(1) Give the configuration (α or β) at the
anomeric carbon joining the first
monosaccharide unit (on the left) to
the second.
(2) Name the nonreducing residue; to
distinguish five- and six-membered
ring structures, insert “furano” or
“pyrano” into the name.
(3) Indicate in parentheses the two
carbon atoms joined by the glycosidic
bond, with an arrow connecting the
two numbers; for example, (1→4)
shows that C-1 of the first-named
sugar residue is joined to C-4 of the
second.
(4) Name the second residue.
Homo- and heteropolysaccharides
Glycogen and starch
Repeating units of some common
Glycosaminoglycans of extracellular
matrix
Starch structure
A schematic block diagram of the
metabolism of a typical aerobic
heterotroph
Stages of catabolism
1. Degradation of polymers to monomers:

 starch, glycogen → glucose;
 proteins → amino acids;
 triacylglycerols → glycerol + free fatty acids.
2. Specific pathways of catabolism of monomers with formation of

simple intermediates – pyruvate and acetylCoA.
 oxidation of glucose to pyruvate, 2 АТP;
 oxidative deamination of amino acids to ketoacids (pyruvate), acetylCoA and
NH3, 2-3 АТP;
 β-oxidation of fatty acids to acetylCoA, 5 ATP.
3. Common pathways of catabolism with formation of end products:

 oxidative decarboxylation of pyruvate to acetylCoA and СО2, 3 ATP;
 oxidation of acetylCoA via Krebs cycle (or citric acid cycle) to
СО2, Н2О, 12 АТP.
Stages of anabolism
1. Third stage of catabolism (amphibolic) – formation of pyruvate and

acetylCoA from intermediates of the citric acid cycle.
2. Specific pathways of anabolism – synthesis of monomers from

pyruvate and acetylCoA:
 synthesis of glucose from pyruvate (gluconeogenesis)
 synthesis of amino acids from pyruvate;
 synthesis of fatty acids from acetylCoA.
3. Conversion of monomers to polymers – glucose to carbohydrates, fatty

acids and glycerol to lipids, amino acids to proteins.
Нigh-energy chemical bonds
Macroergic compounds contain high-energy
1. Pyrophosphate bond chemical bonds releasing energy in excess of
21 kJ / mol during hydrolysis
2. Enol phosphate bond

Нigh-energy chemical bonds
3. Carboxyl phosphate bond
5. Acylthiol bond
4. Carbamoyl phosphate bond

Dietary carbohydrates
Dietary carbohydrates
Stages of carbohydrates digestion
1. Hydrolysis in mouth
2. Hydrolysis in small intestine
3. The absorption in the duodenum and upper jejunum of small intestine
4. Consumption of glucose by cells
Glycosidases in digestion of
carbohydrates
Starch (dextrins), sucrose, lactose and indigestible fiber
Amylase
• Starch to disaccharides (maltose, isomaltose)
(α(1→4) glycosidase)
• α(1-4) glycosyl bonds of maltose to 2 glucoses

Sucrase-isomaltase • sucrose to glucose and fructose
complex • α(1-6) glycosyl bonds of isomaltose to 2 glucoses
Glucoamylase • α (1-4) glycosyl bonds maltose to 2 glucoses

complex • lactose to glucose and galactose
Trehalase • α (1-1) glycosidic bonds in trehalose to glucose
The relative rates of absorption of important monosaccharides:

galactose > glucose > fructose > mannose > xylose > arabinose.
Mechanisms of glucose transport
Active transport
Na+-independent
depending on the
facilitated diffusion
concentration gradient of
transport
Na+
• Sodium-dependent • Facilitated diffusion

receptors receptors (GLUT=glucose
• in kidneys and intestines transporters)
• glucose absorption against • in all tissues
the concentration gradient. • transport according to the
concentration gradient
Different transport mechanisms
for monosaccharides
Stimulation by insulin of glucose
transport into muscle and adipose
cells
The formation of glucose-6-phosphate
Sources of blood glucose
Dietary
carbohydrates
Gluconeogenesis
(synthesis of glucose Degradation of
from noncarbohydrate glycogen
precursors such as (glycogenolysis)
glucogenic amino
acids, lactate, glycerol)
The different metabolic pathways
responsible for the utilization of
blood glucose
1. Source of
energy due to
2. Synthesis of
aerobic (38 ATP)
other
and anaerobic (2
monosaccharides
ATP) glucose
(e.g., pentoses).
oxidation
(glycolysis).
3. Synthesis of 4. Synthesis of
glycogen lipids (e.g., fatty
(glycogenesis) acids,
and other cholesterol),
heteropolysacchar some amino acids
ides in liver and and other
compounds (e.g.,
muscle. glucuronic acid).
Catabolism of carbohydrates
I stage –
II stage – glycolysis
degradation of III stage –citric acid
to pyruvate under
polysaccharides to cycle (Krebs cycle,
aerobic condition
monosaccharides tricarbonyl acid
and to lactate under
(digestion and cycle - TCA)
anaerobic condition
glicogenolis)
The different metabolic pathways
responsible for the utilization of
blood glucose
NAD +

Lecture 9 - Carbohydrates Structure

Uploaded by

Copyright:

Available Formats

Lecture 9 - Carbohydrates Structure

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Lecture 9 - Carbohydrates Structure

Uploaded by

Copyright:

Available Formats

Dr. Elena O. Polovinkina

monosaccharides oligosaccharides polysaccharides

aldoses ketoses tetroses

ribose glucose mannose fructose heptoses

If the chiral carbon farthest from the carbonyl

diastereomers but not

Reaction between the aldehyde group at

anomeric carbon Isomeric forms of

Radicals at the right Radicals below the ring plane

The Fischer projection The Haworth formula

Deoxy sugars - the absence of a hydroxyl group (or groups);

the name describes the compound written

1. Degradation of polymers to monomers:

2. Specific pathways of catabolism of monomers with formation of

3. Common pathways of catabolism with formation of end products:

1. Third stage of catabolism (amphibolic) – formation of pyruvate and

2. Specific pathways of anabolism – synthesis of monomers from

3. Conversion of monomers to polymers – glucose to carbohydrates, fatty

2. Enol phosphate bond

3. Carboxyl phosphate bond

4. Carbamoyl phosphate bond

• α(1-4) glycosyl bonds of maltose to 2 glucoses

Glucoamylase • α (1-4) glycosyl bonds maltose to 2 glucoses

Trehalase • α (1-1) glycosidic bonds in trehalose to glucose

The relative rates of absorption of important monosaccharides:

• Sodium-dependent • Facilitated diffusion

You might also like