Biochemistry 514 Exam I: Carbohydrate Tutorial

Front 1

Steroisomers (isomers)

Back 1

different compounds that have the same structure, differing only in the arrangement of the atoms in space.

Front 2

Chiral

Back 2

Any object that cannot be superimposed on its mirror image, has 4 different groups attached

Front 3

Enantiomers

Back 3

A pair of stereoisomers that are non-superimposable mirror images

Front 4

Diastereomers

Back 4

Non-enantiomeric steroisomers (not mirror images even though they have the same number of each atom). They differ at one or more chiral .carbons

Front 5

Epimers

Back 5

diasteromers that differ at only one of their chiral carbon atoms

Front 6

Anomeric Carbons

Back 6

The carbonyl carbon in any monosaccharide. The carbon that becomes chiral in the cyclization reaction resulting in an alpha or beta sugar

Front 7

Anomers

Back 7

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

Front 8

Furanose ring

Back 8

A monosaccharide in the form of a 5-membered oxygen heterocycle (4 carbons an an oxygen in the ring)

Front 9

Pyranose ring

Back 9

A monosaccharide in the form of a 6-membered oxygen heterocycle (5 carbons and an oxygen in the ring)

Front 10

Carbohydrates

Back 10

Polyhydroxyl aldehydes and ketones and their derivatives

Front 11

Hemiacetal

Back 11

The product of a reaction between an aldehyde and an alcohol

Front 12

Reducing group

Back 12

The aldehyde group or hemiacetal group of an aldose sugar

Front 13

Digestion

Back 13

catalyzed hydrolysis of complex dietary compounds to simpler ones which can be absorbed.

Front 14

Glycosidic bonds

Back 14

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.

Front 15

Dextrin

Back 15

Product of hydrolysis of glycosidic bond of a polysaccharide leaving a relatively large oligo or smaller polysaccharide

Front 16

What determines D and L?

Back 16

The highest numbered asymmetric (chiral) carbon.

Front 17

D sugar

Back 17

-If the highest numbered asymmetric (chiral) carbon has an -OH group pointing to the right.
-Have CH2OH pointing up from ring

Front 18

L sugar

Back 18

-If the highest numbered asymmetric carbon has an -OH group pointing to the left.
-Have CH2OH pointing down from the ring

Front 19

Any group that points to the RIGHT in the Fischer projection, points how in the Haworth structure?

Back 19

Down

Front 20

Any group that points to the LEFT in the Fischer projection, points how in the Haworth?

Back 20

Up

Front 21

Alpha and Beta anomers of sugar

Back 21

-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

Front 22

Are aldoses reducing sugars?
Are ketoses (generally) reducing sugars?

Back 22

Yes aldoses are reducing sugars
Generally ketoses are not reducing sugrs because their anomeric carbon is not free

Front 23

Which is the anomeric carbon for ketones and aldehydes?

Back 23

Ketones: C2
Aldehydes: C1

Front 24

Relationship between Glucose and Fructose?

Back 24

They are isomers NOT diastereomers or epimers bc altering aldehyde to a ketone.

Front 25

How can carbohydrates be modified?

Back 25

Can contain amino, sulfate, and phosphate groups

Front 26

Monosaccharides

Back 26

-simple, single unit sugar
-D-glucose, D-fructose, and D-galactose

Front 27

Disaccharides

Back 27

contain 2 monosaccharides linked by a glycosidic bond
Maltose, sucrose, lactose

Front 28

Polysaccharide

Back 28

long polymer of monosaccharides
starch and glycogen

Front 29

Complex sugar

Back 29

A polysaccharide attached to a non-sugar molecule
Glycoproteins and glycolipids

Front 30

Sugar derivatives

Back 30

Sugars with substitutions or functional groups at one or more of their hydroxyl groups

Front 31

D-glucose

Back 31

Source of energy through glycolysis
-Aldose: aldehyde sugar

Front 32

When an aldose in fischer projection is converted to the ring form, what is produced?

Back 32

A chiral center at C1

Front 33

D-fructose

Back 33

Intermediate in glycolysis
Isomer of D-glycose

Front 34

Isomerases

Back 34

enzyme that converts D-fructose to an D-glucose or vice versa

Front 35

Hemiketal

Back 35

formed by reaction of a ketone and alcohol

Front 36

D-galactose

Back 36

Part of lactose
A building block of many polysaccharides
An epimer of glucose (at C4)

Front 37

Epimerase

Back 37

Enzyme that converts D-galactose to glucose (at C4)

Front 38

is Fructose a reducing sugar?

Back 38

Yes, even though it is a ketone. It exists in equilibrium with its aldose form.

Front 39

Disaccharides

Back 39

-2 monosacchrides linked by a glycosidic bond
-Maltose, Lactose, sucrose

Front 40

Maltose

Back 40

A starch derivative
Glucose + glucose

Front 41

Lactose

Back 41

-Primary sugar found in milk
-Galactose + glucose
-Inability to break this linkage leads to lactose intolerance

Front 42

Sucrose

Back 42

-Not a reducing sugar because no anomeric C is free
-Table sugar
-An inverted sugar (because fructose in inverted)
-Glucose + fructose

Front 43

What C do you look at to determine if a sugar is inverted?

Back 43

Carbon #5

Front 44

Structural Polysaccharides

Back 44

Cellulose, Glycosaminoglycans,

Front 45

Cellulose

Back 45

-Major structural building block of plant cell walls.
-An insoluble fiber
-A glucose polymer with 1,4-glycosidic bonds

Front 46

Glycosaminoglycans

Back 46

-Major structural protein in vertebrates
-One monosaccharide is always N-acetylglucosamine or N-acetylgalactosamine
-Dermatan sulfates (skin), keratan sulfates, and hyaluronic acids (CT)

Front 47

Glucans

Back 47

Polymers of glucose

Front 48

Starch

Back 48

-A glucan
-Principle storage polysaccharide in plants
-Exists in 2 forms: Amylose and Amylopectin

Front 49

Amylose

Back 49

linear polymer of alpha-1,4-glucose linkages

Front 50

Amylopectin

Back 50

Branched polymer of alpha-1,4 and alpha-1,6-glucose linkages

Front 51

Glycogen

Back 51

-A glucan
-Primary storage polysaccharide for animals and microbial cells
-Same branching as amylopectin, but more frequent

Front 52

Complex sugars

Back 52

-Sugar components attached to non-sugar molecules
-Glycolipids, Glycoproteins, Proteoglycans

Front 53

Glycolipids

Back 53

-Blood group antigens
-Complex sugar

Front 54

Glycoproteins

Back 54

-Cell surface antigen
-Complex protein

Front 55

Proteoglycans

Back 55

-Components of the extracellular matrix, has more sugar and less protiens
-Complex sugar

Front 56

Sugar derivatives

Back 56

-Sugar Phosphates
-Deoxysugars
-Amino sugars
-Sugar acids
-Sugar alcohol

Front 57

Sugar Phosphates

Back 57

-Sugars that contain one or more phosphate groups (attached to the OH groups)
-Used in glycolysis and polysaccharide formation

Front 58

Deoxysugars

Back 58

-Formed by the reduction of hydroxyl groups on the sugar
-Essential building blocks of DNA

Front 59

Amino Sugars

Back 59

-Amino derivatives of simple sugars
-Primarily building blocks for polysacchrides and polymers for cartilage and mucous.
-OH replaced by an amine group

Front 60

Sugar acids

Back 60

-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

Front 61

Vitamin C

Back 61

-Has lactone functionality of the carboyxlic acid group

Front 62

Sugar Alcohol

Back 62

-C1 positions of sugars are reduced to alcohols
-Ie: glucose converted to sorbitol