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Biochemistry > Lecture 19, Carbohydrates (Ford) > Flashcards

Lecture 19, Carbohydrates (Ford) Flashcards

1
Q

In constitutional isomers, what changes?

A

Order of atoms

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2
Q

T or F: Constitutional isomers are tautomers.

A

True.

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3
Q

In a tautomer, where does carbon numbering start?

A

Carbonyl end of the aldose

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4
Q

Fisher projections are the ___ versions of carbohydrates.

A

Linear

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5
Q

Describe stereoisomers.

A

Same connectivity, different spatial organizations

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6
Q

What kind of carbons do configurational isomers have?

A

Chiral

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7
Q

Describe enantiomers.

A

Mirror images at all chiral centers

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8
Q

T or F: Diastereomers can have only 1 chiral center, as long as the images do not mirror one another.

A

False. Diastereomers must have multiple chiral centers.

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9
Q

Describe diastereomers.

A

Not mirror images overal

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10
Q

Hawthorne projections are the ___ versions of carbohydrates.

A

Cyclical

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11
Q

Outline how to convert a monosaccharide from a Fisher to a Hawthorne projection.

A
  1. Choose the ring
  2. Carbonyl C goes 1 position CW from the O
  3. Number C CW
  4. =O becomes OH
  5. Left side goes up, right side goes down
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12
Q

When converting from a Fisher to a Hawthorne projection, what do beta and alpha signify when the =O becomes an OH?

A 
Beta = up
Alpha = down
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13
Q

How do anomers differ?

A

At anomeric C only

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14
Q

How do epimers differ?

A

At any other C than the anomeric C

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15
Q

What kind of rotation changes do conformational isomers have?

A

Reversible rotation changes

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16
Q

List the monosaccharides to know.

A

Glyceraldehyde, ribose, glucose, galactose, dihydroxyacetone, ribulose, fructose, D-deoxyribose, D-mannose

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17
Q

When are glycosides formed?

A

When one or more hydroxyls are replaced

18
Q

What can hydroxyls be replaced with to form a glycoside?

A

Fucose, esters (phosphorylation), oxidation/reduction (alcohols), N-linkages (amino sugars, nucleotides), O-linkages (methylation, toxins)

19
Q

Why is fucose weird?

A

Galactose derivative; only L-monosaccharide made and used by mammals; part of A/B/O blood antigens

20
Q

What can excess fucose in the blood lead to?

A

Liver damage, cancer, diabetes, heart disease

21
Q

Describe how monosaccharides can be modified via phosphorylation.

A

Important reactive intermediates in carbohydrate metabolism, adds negative charge, phosphate from ATP

22
Q

What is the relationship between a monosaccharide and a phosphate modification?

A

Name of monosaccharide tells you where to put the phosphate

23
Q

What kind of linkages do phosphates have?

A

Ester

24
Q

Where are reducing sugars oxidized in monosaccharides?

A

Carbonyl

25
Q

What does the oxidation of a monosaccharide make?

A

Acids and lactones

26
Q

What does the reduction of a monosaccharide make?

A

Alditols

27
Q

What can cause cataracts if it accumulates in the lens of the eye?

A

Sorbitol (reduction of carbonyl)

28
Q

Where are monosaccharides that are modified with amino sugars found?

A

In branched polysaccharides (like cell walls)

29
Q

List the essential, regular monosaccharides.

A

D-glucose, D-galactose, D-mannose, D-xylose

30
Q

Of the essential monosaccharides, which is the oddball?

A

L-fucose

31
Q

Of the essential monosaccharides, which are amino sugars?

A

GlcNAc, GalNAc, sialic acid

32
Q

List the essential monosaccharides.

A

D-glucose, D-galactose, D-mannose, D-xylose, L-fucose, GlcNAc, GalNAc, sialic acid

33
Q

List the roles of polysaccharides.

A

Glucose storage, structure, protein diversity

34
Q

Which structural polysaccharide is essentially universal?

A

Chitin

35
Q

List how polysaccharides create protein diversity.

A

Glycoproteins, glycosaminoglycans, mucins

36
Q

T or F: In glycoproteins, protein < sugar.

A

False. In glycoproteins, protein > sugar.

37
Q

What are glycoproteins called on membrane and soluble proteins?

A 
Membrane = cell adhesion
Soluble = cell signaling
38
Q

T or F: In glycosaminoglycans, sugar < protein.

A

False. In glycosaminoglycans, sugar > protein.

39
Q

Describe the structure of glycosaminoglycans.

A

Repeating disaccharide units, sugar component of proteoglycans (cartilage, blood clotting, chitin)

40
Q

In mucins, sugar ___ protein.

A

>

41
Q

What do mucins provide?

A

Lubrication (protection, hydration)

42
Q

How are glycolipids related to blood type?

A

Decorate cell membranes and are used to recognize self/other

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