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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
Numbering Carbons on
Hemiacetals
D-Galactose
-Galactose
-Galactose
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.
More examples
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
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
Chapter 14.6
Polysaccharides
Polysaccharides
A polymer of many monosaccharides joined
together: glycosidic bd
Important polysaccharides:
1.
2.
3.
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
Hydrolysis