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MCAT > Carbohydrate structure and reactions > Flashcards

Carbohydrate structure and reactions Flashcards

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MCAT flashcards
1
Q

What are 10 functions of carbohydrates?

A 
Energy storage
Energy source
Structure 
Components of nucleotides
Protection 
Lubrication
Communication
Information storage 
Mediation of cell adhesion and signalling 
Protein localization and activity
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2
Q

What is the general formula of a carbohydrate? What is n?

A

(CH2O)n. n is between 3 and 7

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3
Q

What functional group does every carbon in a sugar have?

A

Either a carbonyl or a hydroxyl

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4
Q

What is an aldehyde sugar called?

A

Aldose

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5
Q

What is a ketone sugar called?

A

Ketose

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6
Q

What are the 3 class sizes of sugars?

A

Monosaccharides, oligosaccharides, polysaccharides

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7
Q

What type of bond links sugars together?

A

Glycosidic bonds

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8
Q

Are monosaccharides water soluble?

A

Yes, usually

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9
Q

Are oligosaccharides water soluble?

A

Yes, usually

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10
Q

Are polysaccharides water soluble?

A

Not usually

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11
Q

What is a homopolysaccharide?

A

Polymer of only one sugar type

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12
Q

What is a heteropolysaccharide?

A

Polymer of multiple types of sugars

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13
Q

What are glyconjugates?

A

Sugars that are attached to other stuff, namely lipids and proteins

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14
Q

What is the most common number of carbons in a monosaccharide?

A

6

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15
Q

What is the smallest chiral sugar?

A

Glyceraldehyde

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16
Q

What carbon does numbering start at in a sugar ring?

A

The one closest to the carbonyl

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17
Q

How big do sugars need to be to cyclize in solution?

A

At least 4 carbons

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18
Q

How many stereoisomers are there with multiple chiral centres?

A

For n chiral centres, there’s 2^n stereoisomers

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19
Q

What determines if a sugar is D or L?

A

The configuration at the carbon farthest from the carbonyl compared to glyceraldehyde. The D isomer has the hydroxyl on that carbon pointing right

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20
Q

Are most naturally occurring sugars L or D?

A

D

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21
Q

What are epimers?

A

Sugars that differ in stereochemistry only at 1 carbon atom

22
Q

What are enantiomers?

A

Molecules that are non-superimposable mirror images of each other

23
Q

What are diastereomers?

A

Stereoisomers that aren’t mirror images

24
Q

What happens to linear monosaccharides in solution?

A

They are susceptible to nucleophilic attack by alcohols to form hemiacetals or hemiketals

25
Q

The hydroxyl on which carbon will attack the carbonyl in a hexose sugar?

A

Carbon 5

26
Q

What happens to the carbonyl carbon when nucleophilic attack happens?

A

Becomes a hydroxyl that can point either up or down depending on the direction of attack

27
Q

What type of linkage is formed when intramolecular cyclization occurs in a sugar?

A

Ether

28
Q

What is the anomeric carbon?

A

The carbon that formerly had the carbonyl

29
Q

What is the alpha anomer of a hexose sugar?

A

Carbon 6 and the OH on the anomeric carbon are on different sides

30
Q

What is the stereochemistry of an alpha anomeric carbon if there is no carbon 6 hanging off the ring?

A

S

31
Q

What is the beta anomer of a hexose sugar?

A

Both carbon 6 and the OH on the anomeric carbon are on the same side of the ring

32
Q

What is the stereochemistry of a beta anomeric carbon if there is no carbon 6 hanging off the ring?

A

R

33
Q

Is alpha or beta glucose more stable?

A

Beta

34
Q

Why is beta glucose more stable than alpha glucose?

A

Has all the hydroxyls in equatorial positions

35
Q

What is a 6 membered ring called?

A

Pyranose

36
Q

What is a 5 membered ring called?

A

Furanose

37
Q

What are 5 modifications of hexoses that can be made by substituting out a hydroxyl?

A 
Oxidize to COOH
Phosphorylation 
Deoxy sugars 
Amides
Sialic acid
38
Q

What is a reducing sugar?

A

A sugar that can reduce Cu2+

39
Q

Are aldehydes able to be oxidized?

A

Yes, into COOH

40
Q

Are ketones able to be oxidized?

A

No

41
Q

Are aldoses or ketoses reducing sugars?

A

Aldoses

42
Q

Is glucose a reducing sugar?

A

Yes

43
Q

How does glucose testing for diabetes work?

A

Uses glucose oxidase and peroxidase to produce a coloured precipitate

44
Q

What is hemoglobin glycation?

A

Non-enzymatic reaction between glucose and Hb, with glucose reacting with NH2 groups in Hb. More glucose in the blood means more glycated Hb

45
Q

What happens to glycated hemoglobin?

A

Glycation causes rearrangements, oxidations, and dehydrations of hemoglobin, which makes it unusually reactive

46
Q

What does a monosaccharide in solution become when it forms a glycosidic bond?

A

An acetal or ketal

47
Q

What is a glycosidic bond?

A

A bond between any of the OH groups on one sugar and the anomeric carbon on the other sugar

48
Q

What is an O glycoside?

A

The atom in the glycosidic bond is an O

49
Q

What is an N glycoside? Where is this found?

A

The atom in the glycosidic bond is an N. Found in nucleotides and in sugars attached to asparagine

50
Q

How do you name sugars?

A

Have the non-reducing end on the left, then figure out if the anomeric carbon is alpha or beta. Name the monosaccharide with the non-reducing end. Then identify the carbons in the glycosidic bond. Name the second monosaccharide. Continue for a longer chain

MCAT (4 decks)

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