Table of Contents
Composed of carbon, hydrogen, and oxygen
- Acting as the main source of energy for the cell
- Acting as the metabolite for organic compounds eg. fats
- Participating in the structure and functionality of the cell e.g cell membrane liquidity
- Structural components e.g receptors
- Long-term storage of energy for the cell
Classes of carbohydrates
Both monosaccharide and oligosaccharide are soluble in water
- Aldoses – These have aldehyde functional group e.g glucose
- Ketoses – These have keto group eg. fructose
Other classification in terms of the number of carbon atoms
- Trioses – 3 carbon atoms
- Tetroses – 4 carbon atoms
- Pentoses – 5 carbon atoms
- Hexoses – 6 carbon atoms
- Heptoses – 7 carbon atoms
These are disaccharide and trisaccharides
- These are tasteless and insoluble in water
- They include homopolysaccharides and heteropolysaccharides
Two types of isomers
- D and L isomers
- D isomer has an OH group on the right side of the molecule
- L isomer has an OH group on the left side of the molecule
Optical activity of sugars
This is a property exhibited by molecules when a beam, of polarised right, is rotated either to the right or left (dextrorotatory + or levorotatory -) respectively.
- A solution that has an equal concentration of both D and L isomers
- The dextro- and levorotatory activities cancel each other out hence no optical activity in a racemic mixture
- Epimers – This is when two monosaccharides differ from each other in terms of their configuration around a single carbon atom
- Enantiomers – These are stereoisomers which are mirror images of each other
- Diastereoisomers – These are stereoisomers which are no mirror images of each other
what are carbohydrates?
cellulose, sugars, starch
what are the functions of carbohydrates?
provide energy through oxidation; supply carbon for synthesis of cell components; store chemical energy; form parts of cell and tissue structures
carbohydrates have a large number of what kind of functional groups?
hydroxy- aldehydes/ketones (aka, polyhodroxy aldehydes and polyhydroxy ketones)
what is a monosaccharide?
single polyhydroxy aldehyde/ ketone unit
what is a disaccharide?
two monosaccharide units linked together by the acetal or ketal linkages
what is an oligosaccharide?
3-10 monosaccharide units (less common)
what is a polysaccharide?
very large chain of linked monosaccharide units;
polymer consisting entirely of D-glucose units
what are the different types of monosaccharides?
glucose, fructose, galactose
describe the similar structure of D-aldoses
at the top, H-C=O. at the bottom, CH2OH. Differences are in carbons rungs in between.
what is the smallest monosaccharide?
what geometric shape does an L- or D- Glyceraldehyde molecule take?
what is an enantiomer?
each of a pair of molecules that are mirror images of each other.
what is a chiral carbon?
a carbon atom with four different groups attached
what makes a compound chiral?
when two compounds have the same molecular and structural formulas but cannot be superimposed on each other
previous review: generally describe a carbonyl group with R functional groups
where is the carbonyl carbon placed in carbohydrates?
at or near the top
when drawing the D-aldoses (example, d-glucose), how do you determine which side of the polyhydroxide rungs will cycle to the above side of the cyclic formation ring?
the oxygen of the carbonyl group at the top will point to the side which goes above.
what represents a chiral carbon?
The intersection of two lines
There are two kinds of enantiomers; how do we distinguish between the two?
a prefix label of:
L- or “levo” meaning “left”
D- or “dextro” meaning “right”
(for example: D-glucose and L-glucose)
what does the “L-” and “D-” label apply to on the enantiomer itself?
the “L-” and “D-” label applies to the side of the molecule which contains the -OH farthest from the first chiral carbon.
what are sugars called when they contain 3, 4, 5, and 6 carbons?
trioses, tetroses, pentoses, and hexoses
(note, sugars have the “-ose” suffix)
how do we indicate the presence of an aldehyde or ketone group in a sugar?
aldehydes in a sugar contain prefix “aldo-“
ketones in a sugar contain prefix “keto-“
(for example: glucose, a six carbon sugar which contains an R-CHO, or aldehyde, group, is an “aldohexose”; ribulose, a five carbon sugar contains an R1-C=O
R2, a ketone, is a “ketopentose”)
are most monosaccharides aldoses or ketoses? which series do most natural monosaccharides belong to (D- or L-)?
most monosaccharides are aldoses. most monosaccharides belong to the D- series.
Are monosaccharides soluble or insoluble in water? What makes them this way? Why is it important in living organisms?
monosaccharides are extremely soluble in water; this is because of the multiple -OH groups; it is important in living organisms because their solubility allows them to be transported rapidly in the circulatory system.
What do aldehydes and ketones with alcohols react to form?
hemiacetals and hemiketals
what is the general structure of a hemiacetal?
R– C –OH
how does a straight monosaccharide cyclize into a ring (which carbons are active)?
carbon 5 adds to the aldehyde group of carbon 1; predominantly cyclic hemiacetals/hemiketals
what is the general name of the ring formed during monosaccharide cyclization?
a “Pyranose” (pi-ran-ose) ring (a cyclic hemiacetal or hemiketal)
What main change occurs during the cyclization of a monosaccharide into a Pyranose ring?
only the Carbons at positions 1 and 5 change, the rest of the molecule is simply along for the ride.
What are the steps to drawing monosaccharides forming Pyranose and Furanose rings (Halworth Structures)?
beginning with a properly drawn monosaccharide chain…
- draw the ring with its oxygen to the back
- put the anomeric carbon (C-1) on the right side
- the terminal -CH2OH group (C-6) is always shown above the ring for D-monosaccharides
What is the difference between an “α- hydroxyl” and a “β- hydroxyl” pyranose ring?
“α-” means that the -OH on C-1 of the ring is positioned below the ring, and a “β-” means that the -OH on C-1 of the ring is positioned above the ring.
What do we call monosaccharides which form 5-membered rings?
what is an example of a furanose ring?
what is another name for a the C-1 carbon on a Pyranose or Furanose ring?
the “anomeric” carbon
what is an ester? what is its general structure?
a carbonyl adjacent to an ether linkage.
what is benedict’s test?
test to indicate reducing sugars. reduces all monosaccharides and some disaccharides.
how does benedict’s test work?
aldehydes and ketones having adjacent -OH groups are readily oxidized; open chain and cyclic forms of monosaccharides are readily oxidized
what do hemiacetals and hemiketals react with alcohol to form?
acetals and ketals
what is a glycoside?
a glycoside is an acetal or ketal formed from the reaction of cyclic monosaccharides with alcohols in the presence of acid
generally describe glycoside formation
hemiacetal sugar + alcohol —> acetal ring + H2O
what is a glycosidic bond?
when two monosaccharide rings are bonded using a C-O-C bond
what is the main difference between glucose and galactose?
differs in the orientation of -OH group attached to C-4
what does the hydrolysis of disaccharides in presence of dilute acid (or specific enzymes) yield?
hydrolysis of disaccharides yields monosaccharide units
two glucose units joined by a glycoside (C-O-C) linkage between C-1 on the first glucose and C-4 on the second unit; has an “α-” gylcosidic linkage between glucose units (linkage points below).
composed of one molecule of D-galactose and one of D-glucose;
linkage between units is “β-” (1—>4)
composed of glucose and fructose joined by an “α-” linkage from C-1 of glucose and a “β-” linkage from C-2 of fructose
what type of sugar the major storage form of D-glucose in plants?
what color is the reaction between a polysaccharide and iodine?
what are two starch fractions?
amylose and amylopectin
long unbraced chain of D-glucose units connected by an “α-” (1—>4) linkages
what is glycogen?
similar to amylopectin
what is cellulose?
the most important polysaccharide and most abundant compound in nature; provides rigidity and strength to plant cell walls; consists of D-glucose units linked by “β-” (1–>4) linkage
what is galactosemia?
genetic disease (autosomal recessive) in which an enzyme needed to metabolize galactose is deficient or absent; typically develops shortly after birth
what is lactose intolerance?
Congenital disorder consisting of an inability to digest milk and milk products; absence or deficiency of lactase results in an inability to hydrolyse lactose
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