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Biochemistry 2000 - Intro BCHM > Carbohydrates Biochemistry > Flashcards

Carbohydrates Biochemistry Flashcards

1
Q

What are carbohydrates?

A

Essential components of all living organisms and is the most abundant biological molecule on the planet

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2
Q

What is biosynthesis?

A

Structural building blocks+energy storage

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3
Q

What is catabolism?

A

Carbon fuels that drive biological processes.

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4
Q

What is an aldose sugar?

A

An aldose sugar is a molecule that has an aldehyde functional group on C1 of the molecule.

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5
Q

What are the two types of sugars that can be formed?

A

Aldose sugars or ketose sugars.

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6
Q

What are ketose sugars?

A

Ketose sugars have a ketone functional group on carbon 2 of the sugar molecule.

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7
Q

What are the simiplest carbohydrates?

A

The simplest carbohydrates is a molecle that is three carbons long in length and is either an aldose sugar or a ketose sugar.

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8
Q

What is an aldotriose?

A

A 3C long sugar molecule with an aldehyde functional group at C1.

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9
Q

What is a ketotriose?

A

A 3C long sugar molecule with a ketone functional group at C2.

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10
Q

What are monosaccharides?

A

The basic unit of carbohydrates.

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11
Q

Where do monosaccharides come from?

A

Synthesized from simpler substances in gluconeogenesis or photosynthesis.

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12
Q

What is the role of monosaccharides??

A

Major energy source, and components of nucleic acids, and lipid and protein modification.

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13
Q

What are oligosaccharides?

A

Consist of few covalently linked monosaccharides (2~20)
- associated with proteins and lipids
- serve structural and regulatory roles

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14
Q

What are polysaccharides?

A

Consist of ~20 or more covalently linked monosaccharides.
- structural function in all organisms
- nutritional reserve

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15
Q

What are enantiomers?

A

Nonsuperimposable mirror images of one another

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16
Q

What are the two stereoisomers formed by carbohydrates?

A

L and D

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17
Q

What is the most common stereoisomer that carbohydrates exist in?

A

D conformation of the stereoisomer.

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18
Q

How to identify if a carbohydrate is in either the Lor D conformation?

A

Look at the chiral carbon farthest away from the carbonyl carbon.

> OH on left : L isomer
OH on right: D isomer

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19
Q

What is the conformation of a carbohydrate whose farthest chiral carbon (from the carbonyl carbon) has the OH functional group pointing to the left?

A

The conformation of the carbohydrate is the L conformation.

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20
Q

What is the conformation of a carbohydrate whose farthest chiral carbon (from the carbonyl carbon) has the OH functional group pointing to the right?

A

The conformation of the carbohydrate is the D conformation.

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21
Q

What is the proper name of sugar molecules 3C long?

A

(Aldo/Keto) Trioses

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22
Q

What is the proper name of a sugar molecule that is 4C long?

A

(Aldo/keto) Tetroses

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23
Q

What is the proper name for sugar molecules that are 5C long?

A

(Aldo/Keto) Pentoses

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24
Q

What is the proper name for sugar molecules 6C long?

A

(Aldo/Keto) Hexoses.

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25
Q

What are diastereomers?

A

Differ at two or more chiral centers (BUT NOT ALL)

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26
Q

What are enantiomers?

A

Differ at ALL chiral centers (mirror image molecules).

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27
Q

What are epimers?

A

Differ at ONE chiral center.

28
Q

How to determine the number of chiral carbons in a sugar molecule?

A

C-2= # of chiral C in sugar molecule

29
Q

How to determine the number of stereoisomers?

A

2^n, where n is the number of chiral centers in the molecule. Half are D and half are L.

30
Q

What results from a reaction containing alcohols and aldehydes in a 1:1 ratio?

A

Form hemicaetals and (2:1 ratio) acetals.

31
Q

What results from a chemical reaction of alcohols and ketones in a 1:1 ratio?

A

Formation of hemiketals and (2:1 ratio) ketals.

32
Q

Draw the cyclization of glucose.

A
33
Q

What is the name of C1 after cyclization of glucose?

A

It is known as the anomeric carbon (it is a reduced C)

34
Q

What happens to the hydroxyl group during the cyclization of glucose?

A

It becomes a cyclic ether after cyclization has occured.

35
Q

What are the name of 5 member rings?

A

Furanose

36
Q

What is the name for 6 membered rings?

A

Pyranose

37
Q

Draw a generic structure of the formation of a pyranose ring.

A
38
Q

Draw a generic structure of the formation of a furanose ring.

A
39
Q

Draw the structure for beta-D-2-Deoxyribose.

A
40
Q

What is the anomeric carbon?

A

The hemiacetal or hemiketal carbon.

41
Q

What happens through cyclization?

A

Two different anomers (C1 or C2 => chiral) are formed.

42
Q

What is an alpha anomer?

A

Anomeric carbon OH is on the oposite side of the ring from the CH2OH of the chiral C (center) defining D or L.

43
Q

What is a beta anomer?

A

Anomeric carbon OH is on the same side of the ring as the CH2OH of the chiral C (center) defining D or L.

44
Q

Draw the structure of alpha-D-Glucopyranose and beta-D-Glucopyranose.

A
45
Q

Draw the structure for alpha-D-fructofuranose and beta-D-fructofuranose.

A
46
Q

What is mutarotation?

A

The alpha and beta anomeric forms of monosaccharides (and free reducing ends of polymerized sugars) are in equilibrium. Spontaneous interconversion between anomeric forms.

47
Q

Draw the cyclization of fructose.

A
48
Q

Why does fructose exist in a furanose ring conformation than a pyranose ring conformation even though it is 6C long?

A

Fructose is more chemically stable when it is in a 5 member ring (furanose ring conformation) than a 6 member ring conformation (pyranose ring conformation).

49
Q

What are glycosidic bonds?

A

Condensation reaction between anomeric carbon and any other hydroxyl containing compound.

50
Q

What results from the production of a glucosidic bond?

A

Results in chemical formation of Acetal or Ketal

51
Q

What is the most common glycosidic bond observed in disaccharides?

A

Glycosidic bond from C1 to C4.

52
Q

What are other possible glycosidic bonds that can form?

A

C1 to C6
C1 to C1

53
Q

Draw the structure of lactose.

A
54
Q

Draw the structure of trehalose.

A
55
Q

Draw the structure of sucrose.

A
56
Q

How is a glycosidic bond named?

A

alpha/beta-number of anomeric carbon, alpha/beta if also anomeric/number of alcohol carbon

57
Q

Characteristics of polysaccharides.

A
  • variable in length
  • can be comosed of one or more types of monosacharides
  • can be linear or branched
58
Q

What are homopolysaccharides?

A

Composed of one monosaccharide type (same monosaccharide) and can be unbranched or branched

59
Q

What are heteropolysaccharides?

A

Composed of two or more monosaccharide types (different monosaccharides) and can be unbranched or branched

60
Q

What is cellulose?

A
  • Unbranched beta1-4 linked glucose
  • serves structural role in plants
  • indigestible by mammals
61
Q

Draw the structure for cellulose and label glycosidic linkage.

A
62
Q

What is amylose?

A

Unbranched alpha1-4 linked D-glucose

63
Q

Draw the structure of amylose and label the glycosidic linkage.

A
64
Q

What is glycogen?

A

Amylose with alpha1-6 branch every 8-12 residues

65
Q

Draw the structure of glycogen and indicate the glycosidic linkage and the branch points.

A

Biochemistry 2000 - Intro BCHM (2 decks)

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