Lesson 4 “Carbohydrates”

Enantiomers
Carbohydrates
stereoisomers whose molecules are non-superimposable mirror images of each other
the most abundant molecules on earth
Formula:
the main source of energy for living organisms
C6H12O6
mainly contain C, H, O atoms (1:21 ratio)

Occurrence & Functions of Carbohydrates Diastereomers

stereoisomers whose molecules are not mirror images of each other

Formula:

C6H12O6
account for 75% of dry plant material

cellulose (structural component)

starch (stored energy)

Carbohydrates have the ff functions in humans

1. carbohydrate oxidation provides energy

short term energy reserve (glycogen)

Fischer Projection

devised by Emil Fischer in 1891

a two-dimensional representation of a 3D organic molecule by projection

2. carbohydrates supply carbon atoms for the synthesis of other biochemical substances

3. carbohydrates form part of the structural framework of DNA and RNA molecules

4. Carbohydrates linked to lipids are structural components of cell membranes functional groups of high priority are written at the top

draw the rest of the molecules downward

5. Carbohydrates linked to proteins function in a variety of cell-cell and cell-molecule

recognition processes

cell-to-cell recognition

Chirality

mirror image, non-superimposable molecules or the property of ‘handedness’ (isomerism)

left handed form

right handed form

carbon atom attached to 4 different groups or atoms

most carbohydrates have one or more chiral centers

usually denoted by *

Stereoisomers

isomers that have the same molecular and structural formulas but differ in the orientation of
atoms in space

two types

enantiomers

diastereomers
to report the stereochemistry, look at the chiral center at the furthest bottom

if on this carbon, the OH points:

Lesson 4 “Carbohydrates” 1
 right = D sugar

left = L sugar

the most the main mainly account cellulose starch Carbohydrates 1. carbohydrate short term 2. carbohydrates 3. carbohydrates 4. Carbohyd
Occurrence &
abundant source of contain for 75% (structural (stored have the ff oxidation energy supply form part of linked to
Functions of
molecules energy C, H, of dry component) energy)functions in provides reserve carbon atoms the structural lipids are
Carbohydrates
on earth for living O plant humans energy (glycogen) for the framework of structural
organisms atoms material synthesis of DNA and componen
(1:21 other RNA of cell
ratio) biochemical molecules membrane
substances

how can you identify the D isomer of a carbohydrate by looking at the Fischer Projection? based on functional groups:
the -OH group on the chiral carbon farthest from the carbonyl group is pointing to the right aldose - with one aldehyde group

ketose -with one ketone group

Types of Carbohydrates
Monosaccharides

simple sugar; smallest unit that make up any carbohydrate

naturally occurring monosccharides have three to seven carbon atoms; five and six
carbon species are common

pure monosccharides are water-soluble, white, crystalline solids

combined number of C atoms and functional group

Examples;

Aldohexose - monosaccharide with aldehyde group and 6 C atoms

Ketopentose - monosaccharide with ketone group and 5C atoms

Classifications of Monosccharides

based on the number of carbon atoms:

triose - 3C

tetrose - 4C

pentose - 5C

hexose - 6C

D-Glucose D-Fructose

most abundant in nature biochemically the most important ketohexose

most important source of human nutrition aka levulose or fruit sugar

grape fruits are good sources of glucose sweetest tasting of all sugars
also named grape sugar found in many fruits and in honey
other names good dietary sugar due to higher sweetness
dextrose D-Ribose
blood sugar part of a variety of complex molecules which include
D-Galactose

Lesson 4 “Carbohydrates” 2
 milk sugar

synthesized in human beings

found in dairy products, avocados, sugar beets

also present in the chemical markers that distinguish various types of blood -A, B, AB, and O

forms part of glycolipids and glycoproteins in several tisses

part of brain and nerve tissue

D-Glucose vs D-Galactose

Cyclic Forms of Monosaccharides

formed by the reaction of carbonyl group (C=O) with hydroxyl (-OH) group on carbon
5

monosaccharides can exist in open chains but many of them adopt cyclic structures

this is because the cyclic form is lower in energy and thermodynamically more stable
than the open chain

when an alcohol adds to: Disaccharides

an aldehyde = hemiacetal made up 2 monosaccharide units

a ketone = hemiketal joined together by a glycosidic bond

formed via a condensation reaction

2 Cyclic Forms of Glucose (Haworth Projection)
crystalline and water soluble substances
a-Glucose

the OH group of C1 is pointing in the opposite direction of c6

when a glucose are chemically joined together to form a polymer, starch is formed

b-Glucose

the OH group of C1 is pointing in the same direction as c6

when b glucose are chemically joined together to form a polymer, cellulose is formed

Pyranose Condensation - joining two molecules together by removing water

cyclic monosaccharide containing a six-atom ring Maltose

Furanose structurally made of 2D glucose units linked via an a(1-4) glycosidic bond

cyclic monosaccharide containing a 5 atom ring baby foods are rich in maltose

Lactose

made up of B-D galactose and a-D glucose joined by a B(1-4) glycosidic bond

milk is rich in lactose

Sucrose

the most abundant of all disaccharides and found in plants

produced commercially from the juice of sugar cane and sugar beets

sugar can contains up to 20% by mass sucrose

sugar beets contain up to 17% by mass sucrose

made up of a-D glucose and B-D fructose joined by a (1-2) glycosidic bond Stachyose

What do you call the bond that is formed when two monosaccharides react? naturally found in many vegetables (e.g green beans, and other beans) and plants

glycosidic bond
Polysaccharides
through what process are disaccharides formed? what molecule is lost in the process?
made up of 20 or more monosaccharide units
condensation reaction ; water
most carbohydrates found in nature occur as polysaccharides

AKA glycans
Oligosaccharides
two types:
made up of 3-10 monosaccharide units bonded to each other
homopolysaccharide
commonly found in onions, broccoli cabbage, and whole wheat
herteropolysaccharide
Maltotriose
Homopolysaccharide
Maltrotriose is used as a sweetener in cakes, breads, and other confectionery
contain only a single of monosaccharides
Raffinose

it can be found in beans, cabbage, sprouts, broccoli, asparagus, other vegetables, and whole
grains
branched

Heteropolysaccharide Starch Glycogen

contain two or more type of monosaccharides

Lesson 4 “Carbohydrates” 3
 very similar in structure made up of glucose/unbranced

branch points occur every 8-12 glucose branch points occur every 24-30 glucose
branched residues residues

Structural Polysaccharides
Cellulose

unbranched with B(1-4) glycosidic bonds

Characteristics up to 5,000 glucose units

not sweet humans cannot digest cellulose

limited water solubility animals can digest cellulose due to symbiotic bacteria

Examples Chitin

starch and glycogen (storage polysaccharides) similar to cellulose structurally and functionally

gives rigidity to the exoskeletons of arthropods and cell walls of fungi

cellulose and chitin (structural polysaccharides)

hyaluronic acid (acidic polysaccharides) Acidic Polysaccharides

made up of repeating amino units of amino sugar and a sugar with a negative charge
Storage Polysaccharides (heteropolysaccharides)
Starch
Examples:
glucose is the monomeric unit
hylarunonic acid
reserve food supply of plants
heparin
two types based on structure

amylase Hyaluronic Acid

amylopectin alternating units of N-acetyl-B-D glucosamine and D glucuronate
Starch: Amylose highlly viscous and serve as lubricants in the fluid of joints as well as vitreous humor of the
unbranched and accounts for 15-20% of the starch eye

has a (1-4) glycosidic bonds Heparin

takes up less space compared to amylopectin alternating units of 50-90 disaccharide

preferred starch for storage in plants anticoagulant properties used to help prevent clot formation

Starch: Amylopectin

branched and accounts for 80-85% of the starch In starch, two different glucose polysaccharides can be isolated. What are they?

has a (1-4) and (1-6) glycosidic bonds amylose & amylopectin

up to 100,000 monosaccharide units

Glycogen

glucose storage in humans and animals

contains only glucose units

unbranched a(1-4) glycosidic bonds

branched a(1-6) glycosidic bonds

3x more highly branched than amylopectin

contains up to 1,000,000 monosaccharide units

Lesson 4 “Carbohydrates” 4