Lecture 19 (Exam 2)

Question 1

This type of isomers have identical molecular formulas but differ in how the atoms are ordered. They are tautomers.

Answer 1

Constitutional

Question 2

_______ _______ are the linear versions of carbohydrates.

Answer 2

Fisher Projections

Question 3

________ have the same connectivity but different spatial organizations (D or L configuration).

Answer 3

Stereoisomers

Question 4

Configurational isomers have _______ carbons. Meaning they can’t be changed through rotation, bonds have to be broken.

Answer 4

Chiral

Question 5

These are mirror images at all chiral centers.

Answer 5

Enantiomers

Question 6

These are not mirror images overall, but have some changes at stereocenters.

Answer 6

Diastereomers

Question 7

_______ _______ are the cyclic versions of carbohydrates.

Answer 7

Haworth projections

Question 8

What is the first step to drawing monosaccharides (converting from fisher to haworth)?

Answer 8

Choose your ring – 6 or 5 membered ring

Question 9

What is the 2nd step to drawing monosaccharides (converting from fisher to haworth)?

Answer 9

The carbonyl C goes 1 position clockwise from O

***This is called the anomeric carbon

Question 10

What is the 3rd step to drawing monosaccharides (converting from fisher to haworth)?

Answer 10

Number carbons clockwise (starting with the number of the carbonyl carbon)

Question 11

What is the 4th step to drawing monosaccharides (converting from fisher to haworth)?

Answer 11

The =O (always at anomeric carbon) becomes -OH, and UP is beta and DOWN is alpha

Question 12

Anomers differ at the anomeric ______ only (i.e., alpha - hydroxyl down vs beta - hydroxyl up)

Answer 12

Carbon

Question 13

_______ differ at any other carbon than the anomeric carbon (i.e., same alpha or beta but different something else).

Answer 13

Epimers

Question 14

What is the 5th step to drawing monosaccharides (converting from fisher to haworth)?

Answer 14

Left side goes UP

Right side goes DOWN

Question 15

What is the 6th step to drawing monosaccharides (converting from fisher to haworth)?

Answer 15

Once you reach the last carbon before the O in the ring you stop (hydroxyl becomes that O)

Question 16

What is the final step to drawing monosaccharides (converting from fisher to haworth)?

Answer 16

Remaining C’s are rotationally ambiguous, so write them linearly

Question 17

__________ isomers have reversible rotation changes. Can be rotated about a single bond.

Answer 17

Conformational

Question 18

(L/D) configuration means the -OH is to the right of the last stereocenter.

Answer 18

D

Question 19

(L/D) configuration means the -OH is to the left of the last stereocenter.

Answer 19

L

Question 20

These are formed when one or more hydroxyls are replaced.

Answer 20

Glycosides

Question 21

This is a galactose derivative. It is the only L-monosaccharide made and used by mammals, is part of A/B/O blood antigens. Excess of it in the blood can mean liver damage, cancer, diabetes, and heart disease.

Answer 21

Fucose

Question 22

The hydroxyl on the 5th carbon of Fucose is replaced by a…

Answer 22

Methyl

Question 23

These have ester linkages and are part of nucleic acids. They are an important reactive intermediate in carbohydrate metabolism.

Answer 23

Phosphates

Question 24

Phosphates add a ________ charge and come from ATP. The name in the monosaccharide tells you where to put the phosphate.

Answer 24

Negative

Question 25

In this monosaccharide modification, reducing sugars are _______ at the carbonyl. This makes acids and lactones. (Lose hydrogen)

Answer 25

Oxidized (oxidation)

Question 26

An antiquated diabetes urine test is an example of ________.

Answer 26

Oxidation

Question 27

In this monosaccharide modification, ________ at the carbonyl makes alditols. (Add hydrogen)

Answer 27

Reduction

Question 28

Sorbitol is a type of alditol (formed by reduction) that can cause ________ if it accumulates in the lens of the eye.

Answer 28

Cataracts

Question 29

These modified monosaccharides are found in branched polysaccharides and are common additions to proteins. They are N-linked glycosides.

Answer 29

Amino sugars

Question 30

Common additions for amino sugars are...

Answer 30

-Amine -Acetyl Lactic acid

Question 31

This modified monosaccharide is the same reaction that creates polysaccharides, but with a non-sugar...

Answer 31

Methylation

Question 32

Some important toxins are O-linked ________.

Answer 32

Glycosides

Question 33

Role 1 of polysaccharides are glucose ________.

Answer 33

Storage

Question 34

Role 2 of polysaccharides is _______ such as beta-linkages (beta-sheets).

Answer 34

Structure

Question 35

Role 3 of polysaccharides is protein ________.

Answer 35

Diversity

Question 36

This type of protein helps with cell adhesion on membrane proteins and cell signaling on soluble proteins. The protein is greater than sugar (by weight).

Answer 36

Glycoproteins

Question 37

_________ is a glycoprotein that stimulates RBC production and GlcNAc is indicative of cellular energy stores.

Answer 37

Erythropoietin

Question 38

This type of protein has repeating disaccharide units. The sugar is greater than protein (by weight). Sugar component of proteoglycans.

Answer 38

Glycosaminoglycans

Question 39

Examples of glycosaminoglycans are...

Answer 39

Cartilage Blood clotting Chitin

Question 40

This type of protein helps with lubrication, which equals protection and hydration. The sugar is greater than the protein (by weight).

Answer 40

Mucins

Question 41

_________ decorate cell membranes, and are used to recognize self/other. One small addition can be a matter of life or death! For example, with blood types.

Answer 41

Glycolipids