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The document is a student activity sheet for a biology course focused on carbohydrates, outlining lesson objectives, activities, and key concepts related to carbohydrate classification, structure, and function. It emphasizes the importance of carbohydrates in human nutrition and their biochemical roles, including energy provision and structural functions. Additionally, it covers topics such as chirality, stereoisomerism, and the classification of monosaccharides.
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0% found this document useful (0 votes)
22 views40 pagesBIOCHEM SAS 1
The document is a student activity sheet for a biology course focused on carbohydrates, outlining lesson objectives, activities, and key concepts related to carbohydrate classification, structure, and function. It emphasizes the importance of carbohydrates in human nutrition and their biochemical roles, including energy provision and structural functions. Additionally, it covers topics such as chirality, stereoisomerism, and the classification of monosaccharides.
Uploaded by
shaoxmemoirCopyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF or read online on Scribd
/ 40
Course Code: BIO 024
Student Activity Sheet #1
Name: ” set Class number: __
Section: Schedule: Date: _
SL
Lesson titie: CARBOHYDRATES Materials:
Lesson Objectives: by the end ofthis module, you should be Pen, SAS, Snacks
eto...
1. Know what carbohydrates are. References:
2. Understand how carbohydrates are formed. © stoker, H. S.
3. Classify and characterize simple carbohydrates, (2017) Biochemisty (3rd ed).
oligosaccharides, polysaccharides, homaglycans and (M. Finch, Ed.) Belmont CA,
heteroglycans. Usa
4. Identify carbohydrate related diseases o Eentee. D- O17) Ceeinecre
Wustrated Biochemistry (7"
ed.). Lippincott Wiliams &
Wilkins,
I
Productivity Tip: -
Today is quite exciting! Practice this exercise both with your right and left hands. First, imagine that you
have an additional 6” finger. Don't ask why, just imagine. Second, number your fingers but consider your
index as number 1, middle finger as no. 2, ring finger as no. 3 and pinky as no. 4. Lastly, familiarize in your
head the counting and the position of the exercise. You can try doing it from slow until you get faster. Now, if
you already know how it's done, teach someone this hand exercise and the importance of it as you finish
this module. Ooopsss...you might want to add some snacks, ike Piatos, as you progress with your study
today. Have fun!
a a -e “a
° 1 2 12 OQ
— 3 a8 - 2300” 1,23
‘This document is the property of PHINMA EDUCATION Course Code: BIO 024
Ss ree ‘Student Activity Sheet #1
Name; (Class number:
Section: Schedule: Date:
A
1) Introduction (3 min)
Carbohydrates are the most abundant class of bioorganic
molecules on planet Earth. Although their abundance in the
human body is relatively low, carbohydrates constitute about
75% by mass of dry plant materials, Green (chiorophyll-
containing) plants produce carbohydrates via photosynthesis.
In this process, carbon dioxide from the air and water from the
soil are the reactants, and sunlight absorbed by chlorophyll is
the energy source.
compet
Pet eeyme
Plants have two main uses for the carbohydrates they produce. In the form of cellulose, carbohydrates
‘serve as structural elements, and in the form of starch, they provide energy reserves for the plants.
Dietary intake of plant materials is the major carbohydrate source for humans and animals, The
average human diet should ideally be about two-thirds carbohydrate by mass.
Carbohydrates have the following functions in humans:
. Carbohydrate oxidation provides energy.
Carbohydrate storage, in the form of glycogen, provides a short-term energy reserve
Carbohydrates supply carbon atoms for the synthesis of other biochemical substances (proteins,
lipids, and nucleic acids).
Carbohydrates form part of the structural framework of DNA and RNA molecules,
Carbohydrates linked to lipids are structural components of cell membranes.
». Carbohydrates linked to proteins function in a variety of cell-cell and cel-molecule recognition
Processes.
In this module you will lear how carbohydrates are formed through structural arrangement, the
classification and the uses of the different sugars or carbohydrates. This entails you to review basic
‘organic chemistry (refer to the table of functional group).
2) Activity 1: What I Know Chart, part 1 (3 mins)
Instructions: “In this chart reflect on what you know now. Do not worry if you are sure or not sure of
your answers. This activity simply serves to get you started on thinking about our topic. Answer only
the first column, "What | know” based on the question of the second column, Leave the third column
“What I learned” biank at this time
‘What | Know Questions: |
1. raves are major
‘sources of sugar for the body.
True or false?
2. Are all carbohydrates sweet? |
CO; +H,0 + solar energy
> Carbohydrates
one one
What i Learned (Activity 4) |
3. Give at least one medical use
of carbohydrate.
This document is the property of PHINMA EDUCATION S PHINMA EDUCATION
Course Code: BIO 024
Student Activity Sheet #1
Name: ses Class number:
Section: _ Schedule: Date:
B.MAIN LESSON:
‘Activity 2: Content notes (70 min).
Instructions: Please highlight the MOST important information.
Note, it will help if you check the skill building activity first. eye — HOH snaon
mC 0 — kaw
A carbohydrate (C:(H;0):) is @ polyhydroxy aldehyde, a a
Polyhydroxy ketone, or a compound that yields polyhydroxy H-C-on H=C-0H
aldehydes or polyhydroxy ketones upon hydrolysis. The elses cecilae
carbohydrate glucose is a polyhydroxy aldehyde, and the Le oo
Carbohydrate fructose is a polyhydroxy ketone.
CLASSIFICATION OF CARBOHYDRATES
igosaccharide
contains Bwo * contains three fo ten
ichyée or | | ‘ronesetcharde unts mono saccharide units
Bonnvarary ketone ont Covalerty bonded to Covarentiy bonded fo,
cent be broken down eachother each other.
sto simpler units +Suorose (table sugar) +tn.tetrahhexasaccharide
+e Glucose, Fructose *Lactose (mike sugar)
— roe,
opamp aes umepmiay
8 polymenc
“Carbohydrate that
‘contains many
monasaccharde units
covalenty bonded to
each other.
+Ex. celulose, starch
UNDERSTANDING PRINCIPLES ON THE MOLECULAR STRUCTURES OF CARBOHYDRATES
The structures of carbohydrates are far from for being basic and ordinary. However, through the
delicate principles involves from chirality-the handedness in molecules to Haworth projection formulas,
details as to how sugars looks and linked together can be understoad in simple yet challenging ways.
MIRROR IMAGES
First, an important property of many molecules, including most
carbohydrates, is “handedness,” which is a form of isomerism. Molecules that
possess “handedness” exist in two forms: a “left-handed” form and a “right-
handed” form. These two forms are related to each other in the same way
that a pair of hands is related to each other. The relationship is that of mirror
images. A left hand and a right hand are mirror images of each other.
Objects can be divided into two classes on the basis of their mirror images:
objects with superimposable mirror images and objects with
nonsuperimposable mirror images. Superimposable mirror Images are
images that coincide at all points when the images are laid upon each other.
Nonsuperimposable mirror images are images where not all points
coincide when the images are laid upon each other.
Figure 18.5 A port et rt
ght ranoh ae “ot parca
teen ea che
‘This document is the property of PHINMA EDUCATION Course Code: BIO 024
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‘Some, but not all, molecules possess handedness. What determines whether or not a molecule
possesses handedness is the presence of a carbon atom that has four different groups bonded to it in @
tetrahedral orientation. The tetrahedral orientation requirement is met only if the bonds to the four
different groups are all single bonds. The handedness-generating carbon atom is called a chiral center.
A chiral center is an atom in a molecule that has four different groups bonded to it in a tetrahedral
orientation. A molecule that contains a chiral center is said to be chiral. A chiral molecule is a
molecule whose mirror images are not superimposable. Chiral molecules have handedness. An achiral
molecule is a molecule whose mirror images are superimposable. Achiral molecules do not possess
handedness.
CH CBs 9
H—Cc—GQ 9 =H—C—H HE C—CH,CH,
2 7 ff \e
Br Br (CH CH)CE
chiral achiral chiral achiral
‘Does not have 4 diferent Has 4 diferent atoms Only has 3 atoms
‘toms or groups bonded to |] bonded tothe carton: bonded to the carbon
‘he cates “Hy CHs-CHsC Hy HCH, & Ow! double
2 Hydrogens.-CHs-Br CHaCHsCHs bond
The Importance of Chirality
In human body chemistry, right-handed and left-handed forms of @ molecule often elicit different
Fesponses within the body. Sometimes both forms are biologically active, each form giving a different
response; sometimes both elicit the same response, but one form's response is many times greater
than that of the other; and sometimes onty one of the two forms is biochemically active. For example,
studies show that the body's response to the right-handed form of the hormone epinephrine is 20 tmes
greater than ts response to the left-handed form.
Monosaccharides, the simplest type of carbohydrate and the building block for more complex types of
carbohydrates, are almost always “right-handed.” Plants, the main dietary source of carbohydrates,
produce only right-handed monosaccharides. Interestingly, the building blocks for proteins, amino
acids, are always left-handed molecules.
“This document is the property of PHINMA EDUCATION. Course Code: BIO 024
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STEREOISOMERISM: ENANTIOMERS and DIASTEREOMERS
The left- and right-handed forms of a chiral molecule are isomers. They are not constitutional
isomers, but rather are stereoisomers. Stereoisomers are isomers that have the same molecular and
structural formulas but differ in the orientation of atoms in space. By contrast, atoms are connected to
each other in different ways in constitutional isomers.
‘Stereoisomers can be subdivided into two types: enantiomers and diastereomers. Enantlomers
(Enantios- means opposite) are stereoisomers whose molecules are nonsuperimposable mirror images
of each other. Left- and right-handed forms of a molecule with a single chiral center are enantiomers.
Diastereomers are stereoisomers whose molecules are not mirror images of each other. Cis—trans
isomers (of both the alkene and the cycloalkane types) are diastereomers. Molecules that contain more
than one chiral center can also exist in diastereomeric as well as enantiomeric forms.
e Desir meade bev @ J"
Temes we =| “eal, Coaeremen>>
+ ra
|The modocaes are al | Enaeaumners
STEREOASOMIERS.
eneeer: pam (SOMERS. as ie Ss ,
‘ee leas
oS
Tae meena
ENANTIOMERS.
DESIGNATING HANDEDNESS (D,L) USING FISCHER PROJECTION FORMULAS.
Enantiomers are said to be optically active because of the way they interact with plane-polarized
light. An optically active compound is a compound that rotates the plane of polarized light. A
dextrorotatory compound is a chiral compound that rotates the plane of polarized light in a clockwise
direction (means to the right, the Latin dextro means “right). A levorotatory compound is a chiral
compound that rotates the plane of polarized light in a counterclockwise (to the left, the Latin Levo
means “left") direction
A Fischer projection formuta is a two-dimensional structural notation for showing the spatial
arrangement of groups about chiral centers in molecules.
‘This document is the property of PHINMA EDUCATION
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The DL system used to designate the handedness of enantiomers is extended to
monosaccharides with more than one chiral center in the following manner. The carbon chain is
numbered starting at the carbonyl group end of the molecule, and the highest-numbered chiral center is
used to determine D or L configuration. Particularly, the -OH group of the highest chiral carbon
determines the configuration. If the OH is in the right, then it's a D-isomer and if the -OH is in the left,
and then i's an L-isomer.
cH cio (no
buon Son Exon
In the present example, compounds A and B (the first enantiomeric pair) are D-erythrose and L-
erythrose; compounds C and D (the second enantiomeric pair) are D-threose and L-threose. However,
A and C hass @ different relationship since they are epimers. Epimers are diastereomers whose
molecules differ only in the confi guration at one chiral center Other diastereomeric pairs in the present
example are A and D, B and C, and B and D.
STRUCTURES AND CLASSIFICATION OF MONOSACCHARIDE
Although there is no limit to the number of carbon atoms that can be present in a
monosaccharide, only monosaccharides with three to seven carbon atoms are commonly found in
nature. A three-carbon monosaccharide is called a triose, and those that contain four, five, and six
carbon atoms are called tetroses, pentoses, and hexoses, respectively.
Monosaccharides are classified as aldoses or ketoses on the basis of type of carbony! group
present. An aldose is a monosaccharide that contains an aldehyde functional group. Aldoses are
polyhydroxy aldehydes. A ketose is a monosaccharide that contains a ketone functional group.
Ketoses are polyhydroxy ketone!
CHO) ose rupse OYE ENETIOE anyaroracieane
TER) = aes aor |
EHO) | petoae [peruse [nose Rovere
xyore apuose
tyasce
WE. Feros Rensone ‘ose Fem
Gticone sortese
Sharmose
Suinse
‘anctove
Taose
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Monosaccharides are often classified by both their number of carbon atoms and their functional
‘group. A six-carbon monosaccharide with an aldehyde functional group is an aldohexose; a five-carbon
monosaccharide with @ ketone functional group is a Ketopentose. Monosaccharides are also often
called sugars. Hexoses are six-carbon sugars, pentoses five-carbon sugars, and so on. The word
‘Sugar is associated with “sweetness,” and most (but not all) monosaccharides have a sweet taste. The
designation sugar is also applied to disaccharides, many of which also have a sweet taste. Thus sugar
is @ general designation for either a monosaccharide or a disaccharide. Saccharide from the Jatin
Saccharum means suger.
ALDOSES (D-configuration)
3 1,3
23 1,2,3
FAMILIAR???
know ms qute chatengng. But wos it exctng that nay youve pot to eam that iis hand exercise nas meaning? Yes, eye
YYoUcan name them, Lets see about now Keloves would lock ike
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the property of PHINMA EDUCATION PHINMA EDUCATION Course Code: BIO 024
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This table shows the possible number of optical isomer that the sugar (aldoses or ketoses) structures
can be made based on the number of chiral centersicarbons and the location of the hydroxy! (-OH)
group in the each of the chiral centersicarbons. The higher the number of chiral center/carbon, the
higher is the possible number of optical isomer.
[Aldohexose (60) | 4 | 2'=16.8D&8L | * I= chiral carbon—OH atermating right and left
Aldopentose (5c) 2%=8,4D&4L |* 2 chiral carbon — OH alternating 2 rights and 2 lets
‘Aldotetrose (de) 2=4,2DE2L | * 3" chiral carbon — OH sltemating 4 rights and 4 lefts
‘emtezoes (ie) FI=B AD EAL] * A” chiral carbon = OH alternating & rights and 8 eft
HOH,
‘oH oH “
“ "o--H
oH HOH HOH
oH Hon Ht Hon
LOH CHO" CHOW
DAW D-Al DGle DMaa DGu Dide D-Gal D-Tal
Hye Mo mo 4 Wyo go HO
HO--H ‘OH HoH HOH hon ho--H
oH HoH 4-08 4 HOH HOW OH
wot Ho HOH HOH HOH HOH HOH HOH
wot etn won rete Hon wt rote wbx
oHeoH tH HOH aren OH ton 1708
LAll Lealt LGle Man L-Gu Lido Gal L-Tal
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KETOSES (D-configuration)
[===]
oPicue ofinctise =» Serbowe © Tagatone
oe ee
Do you agree that they somehow look the same as akiohexoses? Yes! Although there major difference is
that the second carbon is not a chiral center. Hence, these ketohexose structures that somehow look the
same as ather ahohexoses are epmers at carbon 2
EXAMPLE OF EPIMER:
[p- —[Dmannose |
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IMPORTANT SACCHARIDE
‘D-Ribose ‘Nuclec acids (B-d- | Structural elements of nucleic acids and coenzymes,
(DNA & RNA sugar,| bose and f-d-|eg, ATP, NAD, NADP, flavoprotens. Ribose
ATP sugar} deoxyribose) and ATP | phosphates are intermediates in pentose phosphate
ae
D-Ribulose Formed in metabolic | Ribulose phosphate is an intermediate in pentose
processes phosphate pathway (PPP)
D-Arabinose Gum arabic. Plum and | Constituent of glycoproteins.
|_ cherry gums.
(ylose (aka wood | Wood ‘gums, | Constituent of glycoproteins.
suger proteoglycans,
glycosamnogiycans
D-lynoe Heart cellsimuscie. | A constituent of a fyxoflavin isolated from human heart
muscle
U xylose intermediate t uronic | Found in unine in essential pentosuria
acid pathway.
Present. in the urine
(@tycosuria) in diabetes
melitus owing to raised
blood glucose
“Sugar” of the body since blood
contains dissolved glucose. Normal
glucose level 70-100mg/dL
Primary source of cell's
Frut juices Present in | Can be changed to ghucose in the
Honey in equal amount | liver and 50 used in the body.
wi glucose. ‘Sweetest tasting sugar.
Dietary sugar because less is
needed for the same amount of
sweetness.
Hydrolysis of lactose. | - Can be changed to glucose in the
(Gisaccharide consisting | liver and metabolized
of a ghicose and a |-As brain sugar itis consttuent of | and cataract
galactose unit) since this | glycolipids and glycoproteins found:
sugar does. nat occur free | in brain and nerve tissue.
in nature, Syrthesized in | - D-galactose is present in chemical
the mammary gland to | markers that distinguish various
make the lactose of milk _| types of blood—A, B, AB, and O
Hydrolysis of plant |A constituent’ of many | used for preventing
mannans and gums. alycoproteins urinary act infectons
(UTls) and treating
carbohydrate-deficient
glycoprotein
starch, cane sugar,
makose, end lactose
syndrome,
fan inherited metabolic
disorder,
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CYCLIC MONOSACCHARIDE: HAWORTH PROJECTION FORMULA
Fischer projection formulas are useful for describing the stereochemistry of sugars, but their
long bonds and right-angle bends do not give a realistic picture of the bonding situation in the cyclic
forms, nor do they accurately represent the overall shape of the molecules. Haworth projection
formulas are more useful for those purposes. A Haworth projection formula is @ two-dimensional
‘Structural notation that specifies the three-dimensional structure of a cyclic form of a monosaccharide.
The cyclic forms of monosaccharides result from the ability of their carbonyl group to react
intramolecularly with a hydroxy! group. Structurally, the resulting cyclic compounds are cyclic
‘hemiacetals or hemiketals.
A cyclic monosaccharide containing a six-atom ring is called a pyranase (only aldohexose is
capable), and one containing a five-atom ring is called furanose (aldopentose and ketohexose are
capable of forming) because their ring structures resemble the ring structures in the cyclic ethers pyran
and furan, respectively.
Just like PIATOS, right?
aan
“ann
Dacre
i
anon
SURWORTIE PROJECTION FORMULAS
icRE 16.5 The nae form fo -hacoe emdergen an eremalcaar rection te form
sci hemincrta
‘This document is the property of PHINMA EDUCATION PHINMA EDUCATION Course Code: BIO 024
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The hemiacetal carbon atom present in a cyclic monosaccharide structure atom is called the
anomeric carbon atom. An anomeric carbon atom is the hemiacetal carbon atom present in a cyclic
monosaccharide structure. It is the carbon atom that is bonded to an -OH group and to the oxygen
atom in the heterocyclic ring. Cyclic monosaccharide formation always produces two stereoisomers—
an alpha form and a beta form. These two isomers are called anomers. Anomers ate cyclic
monosaccharides that differ only in the positions of the substituents on the anomeric (hemiacetal)
carbon atom. The 4-stereaisomer has the -OH group on the opposite side of the ring from the -CH2OH
group, and the b-stereoisomer has the -OH group on the same side of the ring as the -CH20H group.
_ -
a
x x OG
CX
a anomer B ssomer
Note: This pyran form is only for ALDOHEXOSES (bonding C1 & C5)
CYCLIC FORMS OF OTHER MONOSACCHARIDE
5
Hot a oe HOCH; --
‘ 1
fou ‘OH
y A
‘On OH OH
eb. Fructone a Ribose
FURAN
FURAN
KETOhexose: C2 &C5 ALDOpentase: C1 & C4
This document is the property of PHINMA EDUCATIO! S PHINMA EDUCATION
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Edge on oxygen atom ring
\WO RTH PROJECTION FORMULA RULES
D or Lisomers:
* Position of CH:OH group of
the highest carbon atom
* D form- CHz0H is aDove
the ring
© L form - CH20H is beLow
the ring
‘Alpha or Beta configuration
(anomers)
* Determines the -CH position
‘of the anomeric carbon (C1 or
C2) in relation to the position
of the highest CH:OH.
© Alpha - 2 groups are in the
‘opposite or “apposite"position
© Beta —2 groups are in the
‘same or “Be same" position
Location of the remaining —OH
© Right-OH = down
(lower down)
© Left-OH = up
(ifted up)
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YMA EDUCATION of PHINMA EDUCATION PHINMA EDUCATION Course Cade: BIO 024
~ —_ Teachers’ Guide Module #1
ame: =
ection: . Schedule:
REACTIONS OF MONOSACCHARIDE
Five important reactions of monosaccharides are oxidation to acidic sugars, reduction to sugar
alcohols, glycoside formation, phosphate ester formation, and amino sugar formation. Remember,
however, that other aldoses, as well as ketoses, undergo similar reactions.
‘Oxidation to Produce Acidic Sugars:
Class number:
Date: _.
The redox —_ chemistry of eas oui
monosaccharides is closely linked to that _-_ Sa
the alcohol and aldehyde functional groups. [=| [sn | =
—
ACIDIC SUGARS
ALDONIC ACID
“Acid group on top
* uses weak oxidizing agent
ALDURONIC ACID
"acid group on bottom
ALDARIC ACID
“acid groups both on top
and bottom
*uses strong oxidizing
jent
"uses enzymes.
cwo
on
Won
Hon tare
Reduction to Produce Sugar Alcohols
The carbonyl group present in a monosaccharide (either an aldose or a ketose) can be reduced
to. hydroxy! group, using hydrogen as the reducing agent. For aldoses and ketoses, the product of the
eduction is the corresponding polyhydroxy alcohol, which is sometimes called a sugar alcohol. For
‘example, the reduction of D-glucose gives D-glucitol.
D-Glucitol aka D-sorbitol have properties similar to those of
the trihydroxy alcohol glycerol These alcohols are used as @ Ga
moisturizing agents in foods and cosmetics because of their toil
affinity for water. D-Sorbitol is also used as a sweetening agent in =f O"
chewing gum; bacteria that cause tooth decay cannot use HOP HOH
Polyalcohols as food sources, as they can glucose and many other non npn
monosaccharides. n-Lon a-Lon
10H HLH
cme canst
ent is the property of PHINMA EDUCATION PHINMA EDUCATION Course Code: BIO 024
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ame: ~ Class number: _
ection: ‘Schedule: Date: ___
Glycoside Formation
Hemiacetals were shown to react pass!
with alcohols in acid solution to produce My
‘acetals. Because the cyclic forms of on no
Monosaccharides are hemiacetals, they "
react with alcohols to form acetals, like o fy
the reaction of b-D-glucose with methyl Pocimone Seay phen
alcohol.
The general name for monosaccharide acetals is glycoside. A glycoside is an acetal formed
from a cyclic monosaccharide by replacement of the hemiacetal carbon -OH group with an -OR group.
It can exist both in alpha and beta form.
Phosphate Ester Formation
The hydroxyl groups of a monosaccharide
can react with inorganic oxyacids to form
inorganic esters. Phosphate esters, formed from
phosphoric acid and various monosaccharides.
For example, specific enzymes in the human
body catalyze the esterifi cation of the hemiacetal
group (carbon 1) and the primary alcohol group
(carbon 6) in glucose to produce the compounds
Qlucase 1-phosphate and glucose 6-phosphate,
respectively.
These phosphate esters of glucose are stable in aqueous solution and play important roles in
the metabolism of carbohydrate:
Amino Sugar Formation
If one of the hydroxyl groups of a monosaccharide is replaced with an amino group, an amino
sugar is produced. In naturally occurring amino sugars, of which there are three common ones, the
amino group replaces the carbon 2 hydroxyl group. The three common natural amino sugars are.
chat chow HOH
0, @.
Ho
on on on
Wo ‘ow ‘on wo) ‘on
-oecnami| Calamani ”
Amino sugars and their N-acetyl derivatives are important building blocks of polysaccharides
found in chitin and hyaluronic acid. The N-acetyl derivatives of D-glucosamine and D-galactosamine
are present in the biochemical markers on red blood cells, which distinguish the various blood types
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DISACCHARIDES.
‘A monosaccharide that has cyclic forms (hemiacetal forms) can react with an alcohol to form a
glycoside (acetal). This same type of reaction can be used to produce a disaccharide, a carbohydrate in
which two monosaccharides are bonded together. In disaccharide formation, one of the
monosaccharide reactants functions as a hemiacetal, and the other functions @s an alcohol,
The bond that links the two monosaccharides of a disaccharide (glycoside) together is called a
glycosidic linkage. A glycosidic finkage is the bond in a disaccharide resulting from the reaction
between the hemiacetal carbon atom -OH group of
‘one monosaccharide and an -OH group on the other oc Semast
monosaccharide. It is always @ carbon-oxygen— — ~~
carbon bond in a disaccharide. que oun
It was noted that a cyclic monosaccharide Ry
contains a hemiacetal (anomeric) carbon atom. Many on 8 On
disaccharides contain both a hemiacetal carbon atom wo
and an acetal carbon atom, as is the case for the on on
preceding disaccharide structure. Hemiacetal and
acetal locations within disaccharides play an important role in the chemistry of these substances.
vag
ue
;
ee cna ec
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Tabulation of disaccharide
Malt sugar
(1/3 as sweet
as sucrose)
Cellobiose
Table sugar
Digestion by
amylase or
hydrolysis of
starch.
Germinating
cereals and
matt.
2 Glucose
units
~a-D glucose
&
- D-glucose
Intermediate in the
hydrolysis of
polysaccharide
cellulose
Nursing mother =
8%
‘Cow's milk = 4-5%
2Glucose units
-f-D-glucose &
-D- glucose
Clinical significance:
In lactase deficiency,
malabsorption leads
to diarrhea and
flatulence. Hence,
lactose intolerance
-(-D-galactose &
-D- glucose
Juice of sugar cane
(20% by mass) &
sugar beets (17% by
mass)
Clinical significance:
In sucrase iency,
malabsorption leads to
diarrhea and
flatulence.
-a-D glucose &
-[+D- fructose
(1-4) (head to
tail)
(1-4) (head to tail)
(1-4) (head to tail)
a,f(1-2)
(head to head)
Cellobiase
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OLIGOSACCHARIDES
‘Are saccharides that contain three to ten monosaccharide units bonded to each other via
Qlycosidic linkages. Two naturally occurring oligosaccharides found
in onions, cabbage, broccoli, brussel sprouts, whole wheat, and
all types of beans are the trisaccharide raffinose and
the tetrasaccharide stachyose.
‘TRISACCHARIDE:
RAFFINOSE composed of
+ @D-galactose
+ aD-ghucose
© = P-D-fructose
‘TETRASACCHARIDE:
STACHYOSE composed of
e-D-galactose
e-Dgalactose
«D-glucose
P-D-ructose
IMPORTANCE OF OLIGOSACCHARIDES
The type of blood a person has (0, A, 8, or AB) is determined by the type of oligosaccharide
that is attached to the person's red blood cells.
Four monosaccharides contribute to the make-up of the oligosaccharide “marking system.”
ve ~ paaeiniasenian
CH, 4
ron on ?
tu és 2
ona fesomnyepacten) e
ant Jontarone Gruen GW-Avwyt Ge Anni-
Ho ® , ..
Note that al thre of the oigossecharile markers hime »
on Ay ceommon fost-mononacchareesoqucr i thot srt
NH
| The atnence or prsrerof 2 th mononaccharle tached
oC, o—t—cH, forthe sevomd galactone determines blood type. Type 0
sh Aenyhngheseme ty eget ‘ood inc hi mononsecharse wi Type A bed hae
N-xcetylgalactoxumime as 2 ffUh unit Type B toad! has p=
Aactone as a fF unit. Type AB Moos contains both type A
fant ype 8 markers,
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aa men Teachers" Guide Module #1
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POLYSACCHARIDES
A polysaccharide is a polymer that contains many monosaccharide units bonded to each other
by glycosidic linkages. Polysaccharides are often also called glycans. Glycan is an alternate name for
@ polysaccharide. Unlike monosaccharides and most disaccharides, polysaccharides are not sweet.
They have limited water solubility because of their size. However, the -QH groups present can
individually become hydrated by water molecules. The result is usually a thick colloidal suspension of
the polysaccharide in water. Polysaccharides, such as flour and cornstarch, are often used as
thickening agents in sauces, desserts, and gravy.
Parameters to distinguish polysaccharides:
1. The identity of the monosaccharide repeating unit(s) in the polymer chain.
2. Homopolysaccharide/glycan - only one type of monosaccharide monomer
b. Heteropolysaccharide/glycan - with more than one (usually two) type of monosaccharide
monomer
2. The length of the polymer chain.
3. The type of glycosidic linkage between monomer units.
4. The degree of branching of the polymer chain.
TYPES OF POLYSACCHARIDES
A. STORAGE POLYSACCHARIDE : used as an energy source in cells. Examples are starch and
glycogen
‘Amylose ‘Amylopectin * 3x more highly branched than
@ -Straight-chain 7a branched glucose amylopectin and it is much larger,
glucose polymer, polymer, accounts for the ‘with up to 1,000,000 glucose units
usually accounts for | remaining 80%-85% of the | _ present.
15%-20% of the ‘starch.
starch More water soluble
© =with 300-500 because of increase in CC
monomer units of branching Ohne Sa Syoee
glucose contains 100,000 glucose
units
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B, STRUCTURAL POLYSACCHARIDE: serves as a structural element in plant cell walls and animal
exoskeletons like chitin and cellulose.
the structural component of plant cell walls, The 2nd most abundant naturally occurring
is the most abundant naturally occurring polysaccharide, next to cellulose.
polysacchande. Function is to give rigidity to the
the “woody” portions of plants—stems, exoskeletons of crabs, lobsters, shrimp,
stalks, and trunks—have particularly high insects, and other arthropods.
concentrations of this fibrous, water- It also has been found in the ceil walls of
insoluble substance. fungi.
Contains 5000 glucose units ‘Structurally identical to cellulose, except the
Nondigestible (human lacks cellulase) monosaccharide present is
N-acetyl-D-glucosamine (rather than
glucose)
ND-glucosamine, product of hydrolysis of
chitin, that is marketed as a dietary
supplement touted to decrease joint
inflammation and pain associated wi
teoarthritis. _
(a) CELLULOSE
cH,OH
0,
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C. ACIDIC POLYSACCHARIDE with a disaccharide repeating unit in which one of the disaccharide
components is an amino sugar and one or both disaccharide components has a negative charge
due to a sulfate group or a carboxyl group. Acidic polysaccharides are heteropolysaccharides.
ex.hyaluronic acid & heparin
‘* small highly-sulfated polysaccharide with
© contains alternating residues of N-
bl . only 15-90 disaccharide residues per chain
scant: Dotcoemmme (UNE) ere + The source for pharmaceutical heparin is
Glucuronate. intestinal or lung tissue of slaughter-house
. animals (pigs and cows). Both with negative
™ D-Glucuronate — is the carboxylate ion charge groups.
formed when D-glucuronic acid loses its
acidic hydrogen atom.
* Highly viscous hyaluronic acid solutions
+ Blood anticoagulant. It is naturally present
in mast cells and is released at the site of
tissue injury.
serve as lubricants inthe fluid of joints, | | HSSUG TINNY. ation of clots in the
© are also associated with the jelly-ike blood and retards the growth of existing
Consistency of the vitreous humor of the clots within the blood. It does not, however,
eye. (The Greek word hyalos means break down clots that have already formed
glass”, hyaluronic acid solutions have a | . The source for pharmaceutical heparin is
glass-like appearance:) Intestinal or lung tissue of slaughter-
house animals (pigs and cows).
SI SY
