Sei sulla pagina 1di 35

Chapter 14.

3
Cyclic Structures of Monosaccharides

Monosaccharides in Nature
The linear form of monosaccharides is
instable - only 1%
C5 and C6 carbs form Hemiacetal or cyclical
form, ringform 99%
Sugars open and close randomly, frequently
Intermolecular rearrangement

Hemiacetals

Glucose:
Hydroxyl group connects: C5 C1 forming a
1,5 ether linkage.
Not a dehydration but a rearrangement!!!

cyclization of glucose
Cyclization of glucose B
Hayworth projection

Hayworth Structure of Glucose

C1 :non-chiral in linear form


but chiral in ring: labeled or

Numbering Carbons on
Hemiacetals

Always start on the right hand side

1,5 Ether Linkage

Cyclic Structure of Galactose


Galactose is an aldohexose that differs from
glucose only with the OH group on carbon 4
With formation of a new hydroxyl group on
carbon 1 galactose also exists in & forms

D-Galactose

-Galactose

-Galactose

Cyclic Structure of Fructose


Fructose is a ketohexose: C5 reacts with
ketone group C2
Smaller ring: pentagon

Fructose Ring numbering

2,5-ether linkage

Chapter 14.5
Disaccharides

1. Linking Monosaccharides
together
Monosaccharides can react with each other
to form di- and polysaccharides (only
ringforms can do that!)
Dehydration Rx: involving the OH groups of
two sugars, splitting out of a water molecule
Formation of an ether linkage called
glycosidic bond ( in sugars only!)
Problem: which OH-groups are reacting?
There are many.

Glycosidic bond formation

Naming of Glycosidic Bonds:


Maltose
Carbon # of first sugar connected to Carbon
# number of second sugar
Maltose: C1 is connected to C4
C1 is also in position
Writing conventions:
(1,4) glycosidic bond
or alpha (1-4)

More examples

Other glycosidic bonds


beta (1-4) glycosidic bond

3 Disaccharides you need to


know
1.
2.
3.

Maltose malt sugar


Lactose milk sugar
Sucrose - table sugar

Generally, a disaccharide is
characterized by.
1. Monosaccharide components
2. glycosidic bonds

Maltose
Monomers: 1. -D-Glucose 2. or -D-Glucose
Glycosidic bond: (1-4)
Creating two chiral versions of Maltose
Maltose
Maltose
-D-Maltose
-D-Maltose

/ of maltose is determined by the C1 position of


second sugar

Whats Maltose Malt Sugar


Obtained from the
hydrolysis of starch
Used in cereals,
candies, and brewing
of beverages

Lactose
Monomers: -D-galactose with -/-Dglucose
Glycosidic bond: (1-4)
Creating two chiral versions of Lactose
-D-Lactose
-D -Lactose

Lactose
Makes up 6-8% of human milk and
4-5% of cows milk
Lactose intolerance: lack of the enzyme
lactase that splits disaccharide during
digestion
Adult Mammals stop expressing the lactase
gene exception: many adult humans have
developed a lactose tolerance
(microevolution) but depends on ethnicity

Sucrose
Monomers: -D-glucose and -D-fructose
Glycosidic bond: , (1,2)
Creating only one form
of D-Sucrose!!!

Sucrose

Commercial sugar, obtained from sugar


beets and sugar cane

Chapter 14.6
Polysaccharides

Polysaccharides
A polymer of many monosaccharides joined
together: glycosidic bd
Important polysaccharides:

1.
2.
3.

Amylose/Amylopectin plant starch


Glycogen animal starch
Cellulose plant fibers

Monomers: all D-glucose but different


glycosidic bonds

Amylose/Amylopectin
Common name starches
glucose storage in plant seeds, tubers etc
Found in grains, potatoes, beans, fruits
Soluble in water
Commercial Starch: mixture amylose 20%
and amylopectin 80%

Amylose
Monomer: -D-glucose (about 200-4000)
Glycosidic bond: -1,4-GB
Enzyme breaking it: Amylase
Structure: Long helical chain

Amylopectin
Monomer: , D-Glucose
Glycosidic Bond: (1,4) and (1,6) GB
(every 25 glucose monomers)
Enzyme breaking it: amylase isozymes
Branched starch

Glycogen

Animal starch
Storage of glucose in the liver
Similar to amylopectin only more branches
(every 10-15 glucose molecules)

Cellulose
Monomers: ,D-glucose
Glycosidic bond: 1,4-glycosidic bonds
Enzyme breaking it: Cellulase
Insoluble in water
straight strands, found in the cell wall of
plants, make plant stalks rigid and strong
Humans, animal, plants DO NOT HAVE the
enzyme cellulase
only bacteria living in the guts of ruminants
have cellulase

Cellulose

Cotton, wood

Digestion of Cellulose
Grazing animals and termites harbor e-coli
who digest cellulose for them
In humans cellulose helps absorb toxins from
digestion of proteins to maintain a healthy
digestive system

Carbohydrates in Our Diet

Hydrolysis

Chemical reaction to separate polymers by


inserting a water molecule

Potrebbero piacerti anche