Académique Documents
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Dr. Alcantara
CARBOHYDRATE
is made up of three different components:
Carbon, Hydrogen & Oxygen.
The empirical formula of of carbohydrates it will be made up of
carbon 2 units or atoms of H and O.
is all about HYDRATES of Carbon. Hydrates because it has a water and
it is made up of carbon. It is where carbohydrate is derived.
It is a polyhydroxy aldehydes or ketones.
Polyhydroxy meaning it contains each of the carbon atoms, it
contains your hydroxyl group.
Fischers projection of Carbohydrates:
Every carbon of it contains your hydroxyl group depending where it is
written on the right or in the left. With the exception of the carbon
that is double bonded with your Oxygen.
1.
as structural elements
cellulose ( plant tissues)
1 | Hazel A. Perilla,RN
PROTEOGLYCAN
It has a sugar acid and an amino sugar but what differs it to the GAGS
is, Proteoglycans have a CORE PROTEIN.
CLASSIFICATION OF CARBOHYDRATES:
1.
2.
3.
Classification
I.
4.
5.
Monosaccharide
Disaccharide
Polysaccharide
Classified according to (a. ) number of carbon atoms and not the sugar units. It
could be made up of 3-10 carbon atoms. The simplest monosaccharide is a 3
carbon atoms while the most complex monosaccharide will be a 10 carbon
atoms. Naturally occurring atoms is just until 6 carbon atoms.
(b.) based on the functional group. The simplest Aldose sugar will be
GLYCERALDEHYDE. And the simplest Ketose sugar will then be
DIHYDROXYACETONE.
You may combine it. e.g. Aldotriose no. of carbon atoms is Triose ( 3 C atoms)
and the functional group is Aldose.
We can name your monosaccharide whether they contain:
5 membered ring (Furanose) or
6 membered ring (Pyranose)
Other FUNCTIONS
Type B D-galactose
Type AB both sugars are present
Type O both sugars are absent
Anticoagulant:
6.
7.
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a.
b.
c.
d.
a.
b.
-
Fischer projection
written in linear or straight chain
C1 should always be written above the chain.
Haworths projection
ring sugar
C1 is the carbon written farthest from your right.
Fischer projection
*Reference carbon: PENULTIMATE CARBON - will always be the
Carbon second from the last C.
If OH is on the right D sugar form
If OH is on the left L sugar form
The most common occurring monosaccharide sugar in nature: D form
b.
Haworth projection
Reference point: LAST carbon attached in the ring.
If OH is written above the plane D sugar
If OH is written below the plane - L sugar
n
3
4
5
6
7
8
Monosaccharide Names/Structures
Category
Triose
Tetrose
Pentose
Hexose
Heptose
Octose
SUGAR:
Reference point: C1 of ring projection ANOMERIC
CARBON
sugar will only be specific to Haworth projection not
seen in Fischer projection.
BUDA Beta Up OH, Down OH Alpha
Q: If you have an aldos/ketose sugar, for you to form a ring, what should be
linked?
A:Penultimate carbon linked to carbonyl group.
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The common name of the above structure is Maltose. Chemical name is Dglucopyranosyl 1,4 D-glucopyranose. The first ends in -syl while the second
will end on -ose.
STEREOISOMERS
Stereoisomers
CHIRAL CARBON
> is a carbon with 4 different atom groups attached on it.
> all monosaccharides will contain a chiral carbon except Dihydroxyacetone.
In here you release the Hydrogen in here, I would release the Hydrogen in 1 of
the bonds of your C = O to make then as your OH. Si H papasoks sa O to become
an OH. Ive added H kaya yung double bond nawala yung isa. This will be the
product CHOH san napunta yung isang H? kay OH. I have then this O atom in
here. Lets try to number it then. Carbon 1 is farthest from the right. This is your
5 and this is your 6 bakit CH nalang? Kasi si OH nawala siya napunta sa C1 kaya
natira nalang si CH in C5. And this one in C6 is CH2OH.
(Top figure) So I have here (lower left figure) downward OH therefore its . Look
at the Fischer projection of glucose (top figure) Look at C2 the OH is on the right
therefore it should be written downward in Haworth projection (Right Down
rule). In C3 left OH thereby it is written upward uin Haworth projection. C4 OH is
on the right therefore it is written donward. In C5 wala nang OH kasi nailink na
sa C1. In C5 and C6 it will depend only whether its D or L form.
Both are glucose in D form, I am going to form between these 2 glucose units.
Between 2 monosaccharides they will be linked by glycosidic bond. So in every
glycosidic bond that is formed Ill be releasing OH and H that is water(H20)
Q: What is formed and released eventually if you form a glycosidic bond? What
is the linkage?
A: WATER H2O. 1,4
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Both are the same but they differ in C234 around their chiral carbon. The one
OH is on the right and the other is on the left.
ISOMERS:
Q: How many number of isomers will Aldohexose have?
2n = no. of possible isomers
n = number of chiral carbons.
A: 24 = 16
Q: How many number of isomers will Fructose have?
A: 6 carbon atoms 3 = 3
23 = 8
In a 5 carbon Ketose sugar, C1 is not a chiral carbon, C2 is not a chiral carbon and
the last one is not a chiral carbon therefore you will just have a 2 chiral carbon.
KETOSE C1, C2 and the last carbon is not a chiral carbon, subtract 3.
In a 6 carbon atoms, you will have 3 chiral carbons because you will subtract the
3 atoms that is not a chira carbon ( C1,C2 & C6).
Q: How many chiral carbons will Aldohexose have?
A: 6 C 2 = 4 chiral carbons.
5 | Hazel A. Perilla,RN
MANNOSE
b. EPIMERS
it will only apply to Fischers projection, straight chain.
- Two sugars that differ only in the configuration around one carbon
very much the same in other carbons.
- The reference sugar is glucose.
a.
b.
CARBINOL GROUP
- There are 2 reactions: Glycosidic & Phosphorylation reaction
- is your alcohol group.
- OH of alcohol group may be linked to:
phosphate or another OH of another group which may or may not be
necessarily another carbohydrate.
- You release water and form an O-glycosidic linkage.
- If you form a glycosidic linkage, you form H2O.
atom but
Anomers
- isomeric forms of
monosaccharides that differ
only in their configuration
about the hemiacetal or
hemiketal carbon atom
[anomeric C ]
Mutarotation
- interconversion of
the and anomers in
aqueous solution
PHOSPHORYLATION reaction
- Donate the phosphate group at C1of glucose to make glucose 1 phosphate.
- Its reaction is also due to carbinol group/alcohol group.
Formation of the 2 cyclic forms of glucose
c. ANOMERS
- It will only apply in a ring structure, Haworths projection
- They only differ at one carbon.
CARBONYL GROUP
- Reactions due to carbonyl group is C=O
a. OSAZONE REACTION
- The carbonyl group of Aldose will be linked to Phenylhydralazine
- The product of the linkage is crystal called OSAZONE.
- All sugars have soluble Osazone. The only sugar without a soluble Osazone will
be MANNOSE.
- The first reaction due to your carbonyl group is OSAZONE formation.
6 | Hazel A. Perilla,RN
REDUCTION
b. OXIDATION REACTION
c. REDUCTION REACTION
In reduction process, the product is sugar alcohol. In glucose the alcohol that is
formed is sorbitol or glucitol and so on. Sorbitol is the one being nitrated and
eventually dehydrated to form the isosorbide mononitrate that is used to treat
Angina. Mannitol is a diuretic.
*Memorize the different tests for Carbohydrates.
The best test for Fructose is Seliwanoffs test because fructose is a hexose and a
ketose. Killianis is used for deoxysugar. Moolisch test is used to test for all
sugars. Bials test is used for pentoses.
OLIGOSACCHARIDES
If we talk about oligosaccharides, we talk about sugar units not the number of
carbon atoms. 2 -10 sugar units is considered oligosaccharides. The simplest
oligosaccharide is Disaccharide.
Disaccharides
A,B,C are all test for the reducing action of your sugar.
Tollens test will not give you a Brick red precipitate instead they will give you a
silver mirror appearance.
RUFF DEGRADATION
Series of reaction that removes the reducing carbon from a sugar and
reduces the number of chiral centers
Ruff degradation is used to remove or cleave the carbon series by removing one
carbon.
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CELLUBIOSE
- contains 2 glucose units
- joined by an -glycosidic linkage bet. C1 of and C4 of glucose
- reducing disaccharide
- point of linkage is 1,4
LACTULOSE
-gal B -1,4 fructose
-non reducing agent because it has a fructose component
-Laxative, hepatic encephalopathy
-Lactic acid, formic acid and acetic acid
OLIGOSACCHARIDES
TRI: RAFFINOSE
TETRA: STACHYOSE
PENTA: VERBASCOSE
HEXA: AJUGOSE
Heteropolysaccharides [heteroglycans]
- contain more than 1 type of sugar unit
[Ex. Heparin, hyaluronic acid, chondroitin
sulfate]
They are labeled either Homo or Hetero polysaccharides. If all are fructose and
contains only 1 sugar or all are glucose, it is classified as Homo. If the sugar unit
contains more than 1 sugar unit it is classified as Heteropolysaccharide. All of
your GAGS are Heteropolysaccharides. Homopolysaccharides are your starch,
glycogen, cellulose & inulin. Starch has a straight chain and it has a branched
chain.
Components of starch
The repeating unit of Inulin is fructose. It is used to test for your glomerular
filtration rate GFR. It can test the filtration of kidney because they are readily
soluble in water. If you take in 500ml and your kidney is functioning, your intake
output must be still 500ml that means you have a well functioning kidneys. The
point of linkage is via 1,2.
CELLULOSE
It is made up of monosaccharide glucose and a disaccharide cellubiose.
* Memorize the component sugar acid and the component amino sugar of each
of these heteropolysaccharide. For e.g. Hyaluronic sugar acid: Acid D-glucoronic
acid amino sugar: N-acetyl, D-glucosamine.
Polysaccharides
I. Heteroglycans
A. Acid mucopolysaccharides (glycosaminoglycans)
group of protective and structural polysaccharides
- mucinsor mucoproteins w/ proteins
- characterized by their content of amino sugar and
uronic acids
1) hyaluronic acid
- (D-glucoronic acid & N-acetyl, D-glucosamine
-endGLYCOGEN
-
Highly branched
Consists of glucose molecules linked by 1,4 linkages in the chain
with branching points every 8 to 12 residues ( 1,6 linkages)
DEXTRIN
This is the product of the incomplete hydrolysis of starch. If you
cleave the starch and not all are cleaved you produce Dextrin. Dextrin is the one
that we are buying in the form of glue. The point of linkage is via 1,2 1,3 &
1,6.
8 | Hazel A. Perilla,RN