Carbohydrates Flashcards
Are polyhydroxy aldehydes and ketones
Carbohydrates
Are simple sugars with 3 to 7 carbons in chain, with carbonyl at either terminal carbon or the carbon adjacent to it
Monosaccharides
Triose which is an intermediate on fructose metabolism
Glyceraldehyde
Tetrose found in blood and cartilage tissue
Erythrose
Pentose found in cells mitochondria and the sugar in RNA
Ribose
Main source of fuel in cell
Glucose
Hexose that can enter glycolysis and produce intermediates for Cellular respiration
Fructose
Examples of Pentoses
Ribose
Arabinose
Xylose
Lyxose
Examples of Hexoses
Allose
Altrose
Glucose
Mannose
Gulose
Idose
Galactose
Talose
Naturally occuring sygars are _____.
D-sugars
Monosaccharide categorized based on
A. Functional group present
B. Total number of OH
C. Number of carbon in exoskeleton
D. Number of Oh at the right position
AC
DL configuration based on _____
Dextro-Levo- based on ____
RS based on ______
Structure
Optical rotation
Cahn-ingold-Prelog Priority
_____ if OH farthest from carbonyl group is at the right
_____ if OH farthest from carbonyl group is at the left
D-sugars
L- sugars
Of all aldohexoses, ___ and ___ are common in nature. With ____ as the most abundant.
Glucose, Galactose
Glucose
____ comes from hydrolysis of starch and cellulose, while ____ comes from hydrolysis of fruit pectins
Glucose
Galactose
Diastereoisomers that differ in configuration around one stereogenic center only
Epimers
Epimeric pair that differ at C4
Galactose-glucose
Epimeric pair that differ at C2
Glucose-mannose
The OH and C=O groups can undergo intramolecular cyclization to form _____
Hemiacetals
Intramolecular cyclization results in formation of a new stereogenic center, called _____
Anomeric carbon
Cyclic hemiacetals of sugars sre drawn using
Haworth projections
_____ with only one anomeric carbon with different configuration
Diastereoisomers
Each cyclic hemiacetal can be isolated and crystallized separately, but when any one compound is placed in solution, an equilibrium mixture of all three forms is formed. This process is called _____
Mutarotation
Upon mutarotation, at equilibrium, the mixture consist of ____ of the alpha anomer, ___ of the beta anomer, and ___ of the acyclic hydroxy aldehyde (open chain form)
37%, 63%, trace amounts
Recall the reactions of the hemiacetal and hydroxyl groups of monosaccharides
1. Glycoside formation
2. N-glycoside formation
3. Ether formation
4. Ester formation
- Hemiacetal OH reacts, changed to OR
- Hemiacetal OH reacts, changed to NHR
- All OH changed to OR
- All OH changed to AcO
Reacll the reactions of the carbonyl group of monosaccharides
1. Reduction
2. Oxidation
3. Wohl Degradation
4. Kiliani-Fischer Synthesis
- Alditol
- Adonic acid, Aldaric acid
- Exoskeleton shortens
- Carbon chain lengthens
Formed when mild oxidizing agents (tollens, benedict, Fehling’s) is used in the oxidation of carbonyl group of monosaccharides.
Aldonic acid
Formed when strong oxidizing agents (HNO3) is used in the oxidation of carbonyl group of monosaccharides
Aldaric acids
Reaction of carbonyl group of monosaccharides that shortens the carbon chain of sugar
Wohl Degradation
Carbohydrates polymers composed of 2-10 suagr units
Oligosaccharides
Linkage that bonds 2 monosaccharides together is called ____
Glycosidic bond
Most abundant disaccharides are ____
Sucrose, maltose, lactose
Trisaccharide with most importance is
Raffinose
Table sugar
Sucrose
Malt sugar
Maltose
Milk sugar
Lactose
Polymers of monosaccharides linked together
Polysaccharide
Identify which classification of polysaccharide:
A. Pectin, alginin acid, xantham gum
B. Starch, cellulose, inulin
A. Heteropolysaccharide
B. Homopolysaccharide
Polysaccharide with only one type of monomer
Homopolysaccharide
Polysaccharide consist of 2 or more type of monomer
Heteropolysaccharide
Linkage of starch is ____ while that of cellulose is _____
Alpha-1,4; beta-1,4
Alpha-1,4 linkage of starch is _____
Amylose
Alpha-1,6 linkage of starch is ____
Amylopectin
General test for all sugar.
Molisch Test
Which is the correct order of series of steps that occurs during Molisch test
A. Oxidation, condensation, dehydration
B. Dehydration, oxidation, condensation
C. Dehydration, condensation, oxidation
C
Test to distinguish pentoses from hexoses
Bial’s test
Chemical characterization that can distinguish ketoses from aldoses
Seliwanoff’s test
____, ____, and ____ can test the presence of non-reducing sugars, which are sugars that have a free anomeric carbon that can reduce oxidizing agent
Tollens, Fehlings, Benedicts test
Chemical characterization that can be used in identification since they have characteristic time of precipitation, crystal forms and melting points
Osazone derivatives
Chemical characterization that can be used in identification since they have characteristic time of precipitation, crystal forms and melting points
Ozlsazone derivatives
Positive sign of reactions for
1. Molisch Test
2. Bial’s test
3. Seliwanoff’s test
4. Benedict’s test
5. Osazone derivatives
- Purple interface for all sugars
- Bluish solution for petoses
- Red solution for ketoses
- Brick red precipitates for non-reducing sugar
- Yellow crystals
Reagents for the ff. test for chemical characterization
1. Molisch Test
2. Bial’s test
3. Seliwanoff’s test
4. Benedict’s test
5. Osazone derivatives
- 1-Naphthol, ethanol, H2SO4
- Orcinol, HCl, FeCl3
- Resorcinol, HCl
- CuSO4, Na2CO3, sodium citrate
- Phenylhydrazine
Reagents for the ff. test for chemical characterization
1. Molisch Test
2. Bial’s test
3. Seliwanoff’s test
4. Benedict’s test
5. Osazone derivatives
- 1-Naphthol, ethanol, H2SO4
- Orcinol, HCl, FeCl3
- Resorcinol, HCl
- CuSO4, Na2CO3, sodium citrate
- Phenylhydrazine