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62 Cards in this Set

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  • Back
Steroisomers (isomers)
different compounds that have the same structure, differing only in the arrangement of the atoms in space.
Any object that cannot be superimposed on its mirror image, has 4 different groups attached
A pair of stereoisomers that are non-superimposable mirror images
Non-enantiomeric steroisomers (not mirror images even though they have the same number of each atom). They differ at one or more chiral .carbons
diasteromers that differ at only one of their chiral carbon atoms
Anomeric Carbons
The carbonyl carbon in any monosaccharide. The carbon that becomes chiral in the cyclization reaction resulting in an alpha or beta sugar
Diastereomers of monosaccharides that differ only in the configuration at carbon 1, for aldose. For ketose, they different at carbon 2. Only exist in cyclic form because in Fischer projection C#1 is not chiral
Furanose ring
A monosaccharide in the form of a 5-membered oxygen heterocycle (4 carbons an an oxygen in the ring)
Pyranose ring
A monosaccharide in the form of a 6-membered oxygen heterocycle (5 carbons and an oxygen in the ring)
Polyhydroxyl aldehydes and ketones and their derivatives
The product of a reaction between an aldehyde and an alcohol
Reducing group
The aldehyde group or hemiacetal group of an aldose sugar
catalyzed hydrolysis of complex dietary compounds to simpler ones which can be absorbed.
Glycosidic bonds
bonds linking sugars to each other in dissaccharides and polysaccharides. They form by the reaction of the -OH grp of a hemiacetal and another alcohol group with the lose of water.
Product of hydrolysis of glycosidic bond of a polysaccharide leaving a relatively large oligo or smaller polysaccharide
What determines D and L?
The highest numbered asymmetric (chiral) carbon.
D sugar
-If the highest numbered asymmetric (chiral) carbon has an -OH group pointing to the right.
-Have CH2OH pointing up from ring
L sugar
-If the highest numbered asymmetric carbon has an -OH group pointing to the left.
-Have CH2OH pointing down from the ring
Any group that points to the RIGHT in the Fischer projection, points how in the Haworth structure?
Any group that points to the LEFT in the Fischer projection, points how in the Haworth?
Alpha and Beta anomers of sugar
-if OH group on C1 for aldoses and C2 for ketoses points DOWN (trans from CH2OH) then ALPHA
-if OH group on C1 for aldoses and C2 for ketoses points UP (cis from CH2OH) then BETA
Are aldoses reducing sugars?
Are ketoses (generally) reducing sugars?
Yes aldoses are reducing sugars
Generally ketoses are not reducing sugrs because their anomeric carbon is not free
Which is the anomeric carbon for ketones and aldehydes?
Ketones: C2
Aldehydes: C1
Relationship between Glucose and Fructose?
They are isomers NOT diastereomers or epimers bc altering aldehyde to a ketone.
How can carbohydrates be modified?
Can contain amino, sulfate, and phosphate groups
-simple, single unit sugar
-D-glucose, D-fructose, and D-galactose
contain 2 monosaccharides linked by a glycosidic bond
Maltose, sucrose, lactose
long polymer of monosaccharides
starch and glycogen
Complex sugar
A polysaccharide attached to a non-sugar molecule
Glycoproteins and glycolipids
Sugar derivatives
Sugars with substitutions or functional groups at one or more of their hydroxyl groups
Source of energy through glycolysis
-Aldose: aldehyde sugar
When an aldose in fischer projection is converted to the ring form, what is produced?
A chiral center at C1
Intermediate in glycolysis
Isomer of D-glycose
enzyme that converts D-fructose to an D-glucose or vice versa
formed by reaction of a ketone and alcohol
Part of lactose
A building block of many polysaccharides
An epimer of glucose (at C4)
Enzyme that converts D-galactose to glucose (at C4)
is Fructose a reducing sugar?
Yes, even though it is a ketone. It exists in equilibrium with its aldose form.
-2 monosacchrides linked by a glycosidic bond
-Maltose, Lactose, sucrose
A starch derivative
Glucose + glucose
-Primary sugar found in milk
-Galactose + glucose
-Inability to break this linkage leads to lactose intolerance
-Not a reducing sugar because no anomeric C is free
-Table sugar
-An inverted sugar (because fructose in inverted)
-Glucose + fructose
What C do you look at to determine if a sugar is inverted?
Carbon #5
Structural Polysaccharides
Cellulose, Glycosaminoglycans,
-Major structural building block of plant cell walls.
-An insoluble fiber
-A glucose polymer with 1,4-glycosidic bonds
-Major structural protein in vertebrates
-One monosaccharide is always N-acetylglucosamine or N-acetylgalactosamine
-Dermatan sulfates (skin), keratan sulfates, and hyaluronic acids (CT)
Polymers of glucose
-A glucan
-Principle storage polysaccharide in plants
-Exists in 2 forms: Amylose and Amylopectin
linear polymer of alpha-1,4-glucose linkages
Branched polymer of alpha-1,4 and alpha-1,6-glucose linkages
-A glucan
-Primary storage polysaccharide for animals and microbial cells
-Same branching as amylopectin, but more frequent
Complex sugars
-Sugar components attached to non-sugar molecules
-Glycolipids, Glycoproteins, Proteoglycans
-Blood group antigens
-Complex sugar
-Cell surface antigen
-Complex protein
-Components of the extracellular matrix, has more sugar and less protiens
-Complex sugar
Sugar derivatives
-Sugar Phosphates
-Amino sugars
-Sugar acids
-Sugar alcohol
Sugar Phosphates
-Sugars that contain one or more phosphate groups (attached to the OH groups)
-Used in glycolysis and polysaccharide formation
-Formed by the reduction of hydroxyl groups on the sugar
-Essential building blocks of DNA
Amino Sugars
-Amino derivatives of simple sugars
-Primarily building blocks for polysacchrides and polymers for cartilage and mucous.
-OH replaced by an amine group
Sugar acids
-The oxidation of either (or both) end carbons of a sugar to a carboxylic acid.
-Often form stable cyclical structures with loss of water to form lactones
Vitamin C
-Has lactone functionality of the carboyxlic acid group
Sugar Alcohol
-C1 positions of sugars are reduced to alcohols
-Ie: glucose converted to sorbitol