Carbohydrates Flashcards
It is polyhydroxy aldehydes or polyhydroxy ketones or
compounds that can be hydrolyzed to them
Carbohydrates`
3 types of Carbohydrates
- Monosaccharides
- Oligosaccharides
- Polysaccharides
Compounds that contain a single carbonyl group and two or more hydroxyl groups
a. monosaccharides
b. oligosaccharides
c. polysaccharides
A.
Cannot be hydrolyzed to simpler carbohydrates
a. monosaccharides
b. oligosaccharides
c. polysaccharides
A.
Have the general formula Cn(H2O)n
a. monosaccharides
b. oligosaccharides
c. polysaccharides
A.
Sugars linked by glycosidic bonds
a. monosaccharides
b. oligosaccharides
c. polysaccharides
B.
Formed when many monosaccharides are bonded together
a. monosaccharides
b. oligosaccharides
c. polysaccharides
C.
3 Functions of Carbohydrates
- Major energy sources
- *Oligosaccharides - Play a key role in processes that take place on the surface of cells, such as cell-cell interactions and immune recognition
- Polysaccharides - essential structural components of several classes of organisms
It is the building blocks of all carbohydrates
a. mono
b. oligo
c. poly
A. Monosaccharides
3 Types of Monosaccharides (AKT)
- Aldose
- Ketose
- Triose
DEtermine what type of monosacharides is this:
- Monosaccharide containing an aldehyde group as part of its structure
a. Aldose
b. Ketose
c. Triose
a. Aldose
Determine what monosaccharides is this:
- Monosaccharide containing a ketone group as part of its structure
a. Aldose
b. Ketose
c. Triose
b. Ketose
Determine what type of monosaccharides is this:
- implest monosaccharide that contians three carbon atoms
- ex. Glyceraldehyde and dihydroxyacetone
a. Aldose
b. Ketose
c. Triose
c. Triose
2 examples of Triose monosaccharides
- Glyceraldehyde
- Dihydroxyacetone
Determine what Triose is this:
- Does not contain a chiral carbon atom
a. Glyceraldehyde
b. Dihydroxyacetone
b. Dihydroxyacetone
Determine what triose is this:
- Does not exist in nonsuperimposable mirror-image forms
a. Glyceraldehyde
b. Dihydroxyacetone
b. Dihydroxyacetone
Determine what Triose is this:
- SImplest carbohydrate that contains a chiral carbon
a. Glyceraldehyde
b. Dihydroxyacetone
A. Glyceraldehyde
DEtermine what type of Triose is this:
- Exists in two isomeric forms that are mirror images of each other
a. Dihydroxyacetone
b. Glyceroacetone
b. Glyceroacetone
2 Stereoisomerism in Monosaccharides
- Stereoisomers (optical isomers)
- Enantiomers
What stereoisomerism in Monosaccharide is this?
- Molecules that differ from each other only in their configuration
a. Stereoisomers
b. Enantiomers
Stereoisomers (optical isomers)
What stereoisomerism in Monosaccharide is this?
- There is Configuration where three-dimensional arrangement of groups around a chiral carbon atom
a. Stereoisomers
b. Enaantiomers
a. Stereoissomers
What stereoisomerism in Monosaccharide is this?
- Mirror-image, nonsuperimposable stereoisomers
a. Stereoisomers
b. Enantiomers
b. Enantiomers
What stereoisomerism in Monosaccharide is this?
- Mirror-image, nonsuperimposable stereoisomers
a. Stereoisomers
b. Enantiomers
b. Enantiomers
What stereoisomerism in Monosaccharide is this?
- has an example of D-glyceraldehyde and L-glyceraldehyde which are enatiomers of each other
a. Stereoisomers
b. Enantiomers
b. Enantiomers
In the streoisomerism in Monosaccharides, T/F.
Is is true that there is a possibility of stereoisomerism increases as the number of carbon atoms increases?
True
It is a wwo-dimensional representations of the stereochemistry of three-dimensional molecules
______ projections.
Fischer Projections
It is where bonds are written in a two-dimensional representation showing the configuration of tetrahedral stereocenters
Fischer Projections
Bonds written _______(horizontally/vertically) represent bonds directed in front of the paper in three dimensions
Horizontally
Bonds written ___________(horizontally/vertically) represent bonds directed behind the paper in three dimensions
Vertically
Fischer Prjections has 3 features.
- Most highly oxidized carbon is written at the top and is designated C-1
- D configuration
- L configuration
In Fischer Prjections, other carbon sequence are nmbered in sequence from the _____ (top/bottom)
Top
In Fischer Projections, D configuration:
- —OH is on the ____(right/left) of the highest-numbered ciral number.
Right
—OH is on the right of the highest-numbered chiral carbon
a. D configuration
b. L configuration
a. d configuration
In Fischer Projections, L configuration:
- —OH is on the ____(right/left) of the highest-numbered ciral number.
Left
—OH is on the left of the highest-numbered chiral carbon
a. D configuration
b. L configuration
b. L configuration
Contain two chiral carbons, C-2 and C-3, and four possible stereoisomers
a. Aldotetroses
b. Triose
a. Aldotetroses
It is where two isomers have the D configuration, and two have the L configuration
a. Aldotetroses
b. Triose
a. Aldotetroses
2 types of Aldotetroses
- Diastereomers
- Epimers
Determine what type of Aldotetroses:
- Nonsuperimposable, non–mirror- image stereoisomers
a. Diastereomers
b. Epimers
a. Diasteereomers
Determine what type of Aldotetroses:
- Where L-threose is a diastereomer of both D- and L-erythrose
a. Diastereomers
b. Epimers
a. Diastereomers
Determine what type of Aldotetroses:
- Diastereomers that differ from each other in the configuration at only one chiral carbon
a. Diastereomers
b. Epimers
B. epimers
Determine what type of Aldotetroses:
- has an example of D-erythrose and D-threose are epimers
a. Diastereomers
b. Epimers
b. Epimers
Streochemical Relationships among Monosaccharides
Hierchy: 1
D-Glyceraldehyde
Streochemical Relationships among Monosaccharides
Hierchy: 2
- It is under D-Glyceraldehyde
- D-Erthrose
- D-Threose
Streochemical Relationships among Monosaccharides
Hierchy: 3 left side
- It is under D-Erythrose
- D-Ribose
- D-Arabinose
Streochemical Relationships among Monosaccharides
Hierchy: 3 right side
- It is under D-Threose
- D-Xylose
- D-Lyxose
Streochemical Relationships among Monosaccharides
Hierchy: 4 (Last, bottom)
- It is under D-Ribose
- D-Allose
- D-Altrose
Streochemical Relationships among Monosaccharides
Hierchy: 4 (Last, bottom)
- It is under D-Arabinose
- D-Glucose
- D-Mannose
Streochemical Relationships among Monosaccharides
Hierchy: 4 (Last, bottom)
- It is under D-Xylose
- D-Glucose
- D-Idose
Streochemical Relationships among Monosaccharides
Hierchy: 4 (Last, bottom)
- It is under D-Lyxose
- D-Galactose
- D-Talose
Cyclization of sugars takes place because of interaction between functional groups on distant carbons, such as C-1 and C-5, to form a cyclic hemiacetal in aldohexoses
a. Hemiacetal
b. Hemiketal
a
Determine what Cyclic Sugar:
- Compound that is formed by the reaction of an aldehyde with an alcohol
Hemiacetal
Determine what cyclic sugar:
- Compound that is formed by the reaction of a ketone with an alcohol
Hemiketal
Cyclization due to interaction between C-2 and C-5
results in hemiketal formation in ketohexoses
a. Hemiacetal
b. Hemiketal
b. Hemiketal
In both cases of Hemiacetal and Hemaketal, what do you call the carbonyl carbon that becomes a chiral center?
Anomeric Carbon
One of the possible stereoisomers formed when a sugar assumes the cyclic form
Cyclic Structure: ______
Anomers
Cyclic structures are shown in perspective drawings
as planar five- or six-membered rings viewed nearly
edge on
a. Fischer Projection
b. Haworth Projection
b.
Determine what Haworth Prjection Formula is this:
- Cyclic sugar with a five-membered ring Structures
a. Furanose
b. Pyranose
a. Furanose
2 types of Haworth Projection Formulas
- Furanose
- Pyranose
Determine what Haworth Prjection Formula is this:
- Rings are very nearly planar
a. Furanose
b. Pyranose
a. Furanose
Determine what Haworth Prjection Formula is this:
- Cyclic form of a sugar containing a six-membered ring
a. Furanose
b. Pyranose
b.
Determine what Haworth Prjection Formula is this:
- Rings exist in solution in the chair conformation
a. Furanose
b. Pyranose
b. Pyranose
Designation of Haworth Projection Formulas:
- β- means that —OH on the anomeric carbon is
a. cis
b. trans
a. Cis
Designation of Haworth Projection Formulas:
- β- means that —OH on the anomeric carbon is
a. cis
b. trans
Redox Reactions of Simple Sugars**
Aldehyde groups can be oxidized to give the _____
group
Carbonyl gorup
Redox Reactions of Simple Sugars**
Aldoses are _______ that contain a free carbonyl group and can react with an oxidizing agent
reducing sugars
Redox Reactions of Simple Sugars**
- Ketoses can also be _______ because they isomerize to aldoses
reducing sugars
Redox Reactions of Simple Sugars**
- Oxidation of a cyclic hemiacetal form gives a ______, which is a cyclic ester linking the carboxyl group and one of the sugar alcohols
lactone
Redox Reactions of Simple Sugars**
- What test is used to detect the presence of reducing sugars?
Tollens test
Redox Reactions of Simple Sugars**
- What is used as the oxidizing agent?
Ag(NH3)2+ - Silver ammonia
Redox Reactions of Simple Sugars**
- What would be the result in Tollens reagent test if anomeric carbons are involved in a glycosidic linkage?
Positive or Negative
Negative
Redox Reactions of Simple Sugars**
- What would be the result in Tollens reagent test if another anomeric carbon is not bonded and is free?
Positive or Negative
Positive
What do you call the reduced sugars in which a hydrogen atom is substituted for one of the hydroxyl groups of the sugar
Deoxy Sugar
What do you call the Polyhydroxy alcohols that result when the carbonyl group of a sugar is reduced to a hydroxyl group
Alditols
Order of Alditols
- D-Sorbose
- D-Sorbitol
- D-Xylitol
- D-Xylulose
Sugar Esters
What do you call the Intermediates in the breakdown of carbohydrates to provide energy
Phosphate Esters
Sugar Esters
It is Formed by transfer of a phosphate group from ATP to give the phosphorylated sugar and ADP
Phosphate esters
Formation of Glycosidic Bonds
- What do you call the compound formed when a hemiacetal carbon reacts with an alcohol to give a full acetal
Glycoside
Formation of Glycosidic Bonds
- Resulting bond is called ____.
Glycosidic bond
Formation of Glycosidic Bonds
- Glycosides involving a furanose
Furanosides
Formation of Glycosidic Bonds
- Glycosides involving a pyranos
Pyranosides
Formation of Glycosidic Bonds
- Glycosidic bonds between monosaccharide units are the basis for the formation of _______ and _______.
Oligosaccharides and Polysaccharides
Formation of Glycosidic Bonds
- T/F: Glycosidic lingkages take many forms
True
(Anomeric carbon of one sugar can be bonded to any one of the —OH groups on the second sugar to form an α- or β-glycosidic linkage)
Formation of Glycosidic Bonds
- Anomeric form of the sugar that is involved in the bond
- Carbon atoms of the two sugars that are linked together
none of
Two Different Disaccharides of α- D-Glucose
- α (1–>4) Glycosidic bond
- α (1–>6) Glycosidic bond
A Disaccharides of β-D-Glucose
β, β (1–>1) GLycosidic bond
A Disaccharides of β-D-Glucose
