Carbohydrates Flashcards
The most common source of energy is a biomolecule called what?
carbohydrate
Carbohydrates provide chemical energy in what forms?
3 carbs that provide energy?
- Glucose
- Starch
- Glycogen
Carbohydrates, in plants, are components of supportive structures. What do u call this carb?
present in plant cell walls
cellulose
What are the two carbohydrates present in nucleic acids?
- D-ribose
- 2-deoxy-D-ribose
Before, scientists thought of Carbohydrates as hydrates of what?
Carbon
What is the empirical formula of Carbohydrates?
Cn(H2O)m
Glucose or Galactose, for example, is a carbohydrate w/ a general formula C6H12O6. Divide these by a factor of 6 and you’ll be left w/ CH2O which is a “hydrate of carbon” (C w/ water)
At the molecular level, most carbohydrates are what?
poly + functional grp (2 ‘to)
- polyhydroxyaldehydes
- polyhydroxyketones
or compounds that yield them after hydrolysis
What do you call the carbohydrates w/ a single sugar molecule?
monomer of carbs
Monosaccharides
____ are monosaccharides containing an aldehyde group; whereas ____ are monosaccharides containing a ketone grp
Aldoses; Ketoses
In the naming of carbohydrates, the suffix -____ indicates that a molecule is a carbohydrate.
-ose
In the naming of carbohydrates, the prefixes tri-, tetr-, pent-, etc. indicate what?
no. of carbon atoms in the chain
What do you call the simplest monosaccharides that contain three carbon atoms?
Trioses
There are only two trioses, what are they?
- Dihydroxyacetone
- Glyceraldehyde
Among the two trioses, which of them does not contain a chiral carbon atom?
Dihydroxyacetone
since no chirality present, this molecule does not have nonsuperimposable mirror-image forms (enantiomers)
Among the two trioses, which of them has a chiral carbon?
Glyceraldehyde
since there is chirality at carbon number three, there are two possible enantiomers of Glyceraldehyde: L- & D-Glyceraldehyde
The possibility of ____ increases as the number of carbon items increases.
optical isomerism
stereoisomerism
What do you call the 2-D representations of the stereochemistry of 3-D molecules?
Fischer projections
In Fischer projections, the horizontal lines represent bonds directed ____ you. The vertical lines signify that bonds are directed ____ from you.
away or toward
towards; away
dark wedges = towards u (out of the page); broken lines = away (into the page)
Who proposed the Fischer projections?
Emil FIscher
in 1891 :ooo
The D in D-enantiomer means? While L is for?
Dextrorotary; Levorotatory
L- and D- refers to the direction of rotation of plane-polarized light (clockwise or counterclockwise). Glyceraldehyde has a specific rotation of how many degrees?
+-13.5o
What monosaccharide served as the reference point for the enantiomers of all the other aldoses and ketoses?
glyceraldehyde
What do you call the Carbon that is the reference point wherein it is the next-to-the-last carbon on the chain?
penultimate carbon
A monosaccharide that, when written as a Fischer projection, has the -OH group on its penultimate carbon to the right
D-Monosaccharide
A monosaccharide that, when written as a Fischer projection, has the -OH group on its penultimate carbon to the left.
L-Monosaccharide
What do you call the monosaccharide that have four possible stereoisomers due to two chiral carbons?
Aldotetroses
2 isomers are D; 2 are L. One of each two is an epimer
What do call the diastereomers that differ from each other in the configuration at only one chiral carbon?
Epimers
The D- and L- configuration may be determined by looking at the -OH group at the ____-numbered carbon
highest or lowest
highest
In naming carbohydates, remember that we start where the aldehyde or ketone grp is. Usually, the highest-numbered carbon is the one away from the aldehyde/ketone grp
The highest-numbered carbon may be also called as what carbon?
the orientation of this carbon determines the D or L configuration
penultimate carbon
What are the most important monosaccharides to us?
hexoses found prominently in our metabolism
- D-glucose
- D-galactose
- D-fructose
Also known as dextrose, what is the most common hexose that is an aldohexose?
D-glucose
found in honey, corn syrup, veggies, fruits and in our blood
normal glucose concentrations in the blood would be?
mg/dL
65 - 110 mg/dL
1mM=18mg/dL
hyper or hypoglycemia :oo
It is the sweetest of the carbohydrates, being twice as sweet as table sugar. What is this monosaccharide?
D-fructose
D-fructose is also called what?
- levulose
- fruit sugar
Like the most common hexose, this one is also an aldohexose and is found in milk and dairy products, what do u call this monosaccharide?
D-Galactose
What do you call the condition when a person is missing the enzyme that converts D-galactose to D-glucose?
Galactosemia
Galactoose accumulates in the blood & tissues, leading to cataracts, mental detardation, and liver disease.
With pentoses and hexoses, the most stable forms are actually ____ structures containing five or six atoms.
ring
What do you call the way of representing the cyclic structure of monosaccharides?
Haworth projection
A way to view furanose and pyranose; the ring is drawn flat and viewed through its edge, with the anomeric carbon on the right and the oxygen atom to the rear.
Haworth projection
What do you call the hemiacetal carbon of the cyclic form of a monosaccharide?
Anomeric carbon
What do you call the monosaccharides that differ in configuration only at their anomeric carbons?
Anomers
What do you call the new carbon stereocenter created in forming the cyclic structure that is based on FIscher projection?
Anomeric carbon
Stereoisomers that differ in configuration only at the anomeric carbon are called ____.
Anomers
The anomeric carbon of an aldose is carbon number what in haworth projections?
Carbon 1
The anomeric carbon of ketoses are carbon number what?
Carbon 2
Cyclization of sugars takes place because of interactions between functional groups on distant carbons.
The -OH grp in Carbon number what attacks the Carbon-1in fischer projections to form a cyclic hemiacetal in aldohexoses?
Carbon-5 or Carbon-4
nucleophilic attack ng -OH grp
C-4 hydroxyl attacking the carbonyl group will lead to the formation of a 5-membered ring, while the attack of C-5 hydroxyl at the carbonyl group will generate a 6-membered ring. In the case of glucose, a 6-membered ring is thermodynamically more stable than a 5-membered ring, thus favoring the formation of a 6-membered ring over a 5-membered ring.
Khan cyclic hemiacetals
On Fischer projections, the substituents of the stereocenters located right are pointing where in Haworth projections?
pointing down
only exemptions, if u’ll notice, are carbons 5 & 6. This is because the OH of the nucleophilic carbon needs to be in a desirable location (nearest the aldehyde or ketone). So the substituents of these groups rotate in a counterclockwise manner so that -OH of C-5 will easily attack the aldehyde.
Ochemtutor timestamp
On Fischer projections, the substituents of the stereocenters located left are pointing where in Haworth projections?
pointing up
only exemptions, if u’ll notice, are carbons 5 & 6. This is because the OH of the nucleophilic carbon needs to be in a desirable location (nearest the aldehyde or ketone). So the substituents of these groups rotate in a counterclockwise manner so that -OH of C-5 will easily attack the aldehyde.
Ochemtutor timestamp
What do you call a six-membered hemiacetal ring?
pyranose
indicated by -pyran-
corresponds to the shape of the heterocyclic compound pyran
What do you call a five-membered hemiacetal ring?
furanose
indicated by -furan-
corresponds to the shape of the heterocyclic compound furan
On Fischer projections, the -OH grp at the anomeric carbon that is located right are what types of anomers in Haworth projections?
α-anomer
In Fisher projections, the ones located on the right are pointing down. since we know that CH2OH is pointing up on Haworth, the α- designation means that the -OH is trans to CH2OH
On Fischer projections, the -OH grp at the anomeric carbon that is located left are what types of anomers in Haworth projections?
β-anomer
In Fisher projections, the ones located on the left are pointing up. since we know that CH2OH is pointing up on Haworth, the α- designation means that the -OH is cis to CH2OH
In Haworth projections, the α- designation means that the -OH of the anomeric carbon is ____ to CH2OH
cis or trans?
trans
CH2OH is pointing up while the -OH grp of the anomeric carbon is pointing down
In Haworth projections, the β- designation means that the -OH of the anomeric carbon is ____ to CH2OH
cis or trans?
cis
CH2OH is pointing up and the -OH grp of the anomeric carbon is pointing up too
Because the α- and β- forms of glucose are six-membered cyclic hemiacetals, they are named ____ & ____, respectively
α-d-glucopyranose; β–d-glucopyranose
The designations -furan- and -pyran- are sometimes omitted in monosaccharide. Thus, the glucopyranoses, for example, are often named simply as what?
α-d-glucose & β-d-glucose
The most prevalent forms of D-ribose and other pentoses in the biological world are ____.
furanoses or pyranoses
furanoses
remember that the sugar grps in nucleics are pentoses (aldopentoses) and are 5-membered rings ryt
What do you call the change in specific rotation that occurs when an α or β form of a carbohydrate is converted to an equilibrium mixture of the two forms?
Mutarotation
α-D-glucose has a specific rotation of how many degrees?
+112o
this is how much it rotates plane-polarized light
β-D-glucose has a specific rotation of how many degrees?
+18.7o
this is how much it rotates plane-polarized light