Exam 2: Macromolecules: Carbohydrates Flashcards

1
Q

characteristics of macromolecules

A
  • building blocks of living organisms
  • polymers of individual subunits/monomers
  • all contain carbon and hydrogen, most oxygen
  • C-C bonding forms rings or chains that functional groups can attach to
  • functional groups affect structure and function
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2
Q

Carbon functions

A
  • forms 4 bonds for stability
  • able to bind other carbons
  • forms complex structures such as rings and chains
  • able to form single as well as multiple bonds
  • HAVE CHIRALITY
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3
Q

what does chirality mean?

A

a carbon with 4 different bonds

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4
Q

what are stereoisomers?

A

4 unique groups arranged in different ways

- same formula, dif 3D shape

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5
Q

D (R) isomers rotate light how?

A

clockwise

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6
Q

L (S) isomers rotate light how?

A

counterclockwise

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7
Q

Which form do racemic mixtures have

A

both D and S

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8
Q

Why is stereochemistry important in pharmecuticals?

A
  • stereoisomers have same chemical formula and attachments, but differ in spatial arrangements
  • effects binding ability and affinity
  • binding poorly to the target effects the efficacy
  • binding a site other than the target site can be disastrous
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9
Q

History of thalidomide in US

A
  • Taussing : treated these people
  • Kelsey: FDA, refused to do this, both said no
    not a lot of cases in US. many elsewhere
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10
Q

Thalidomide

A

developed to treat nausea
- R version is sedative, calms people down
one form effective and the other not
- R worked well in pregnant women
- S is a terotegen:
causes defects in unborn in development of arms and legs receptors

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11
Q

4 main categories of macromolecules

A

carbohydrates, lipids, proteins, nucleic acids

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12
Q

Carbohydrate functions

A
  • energy, storage, structure
  • cell recognition and communication
  • modifies proteins effecting
    - structure/folding, enzyme kinetics,
    turnover/degradation
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13
Q

Structure of carbohydrates

A

monomer: CH2O

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14
Q

carbohydrate terminology

A

ose: refers to sugars

mono, di, poly refers to degree of polymerization

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15
Q

Two examples of simple sugars

A

glucose and fructose

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16
Q

what is the difference between glucose and fructose?

A

glucose is an aldose sugar (carbonyl on end)

fructose is a ketose sugar (carbonyl in middle)

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17
Q

similarities between glucose and fructose

A

both D-isomers, right handed

we only use Right form

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18
Q

If many chiral carbons how do we know what form it is in?

A

highest chiral carbon, look at the OH group

- if written on the right it is right handed

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19
Q

What if bacteria could make left handed form in protective capsule?

A

it is better for them, they get added defense that we cannot break down

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20
Q

What if you ate breakfast and all sugars were left handed?

A

enzymes would not fit into the active site
transporters could not bind to get it out so it would stay in the gut
- attracts water to it since hydrophilic so you get diarrhea

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21
Q

alpha form of carbohydrates

A

opposite sides

OH in the down position

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22
Q

beta form of carbohydrates

A

same side

OH in up form

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23
Q

anomeric C

A

one with carbonyl

forms the ring

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24
Q

Binding to find Di/Polysaccharides

A

condensation, dehydration rxn to remove water (OH from one, H from other) and combine sugars

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25
Q

What type of bond is between sugars

what things have these bond

A

alpha 1-4 glycosidic bond

starch and sucrose

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26
Q

What types of bonds does glycogen have?

A

a 1-4 and a 1-6 glycosidic bonds

gets branched structure

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27
Q

glycogen

A

primary carbohydrate storage molecule

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28
Q

what type of bonds does lactose have?

A

B1-4 glycosidic bond

29
Q

Why might someone who has no problem digesting sucrose or starch have difficulty with lactose?

A

need different enzyme for B bonds

need lactase

30
Q

How is lactase made?

A

in Small Intestine from mucosa and it can dec over time in some cases
- causing an intolerance to lactose

31
Q

amylase

A

breaks down all alpha bond

32
Q

Where is lactase only produced?

A

the mucosa of the small intestines

33
Q

When does lactose intolerance occur?

A

when your body stops producing lactose

34
Q

Is lactose intolerance permanent?

A

it can be temporary or genetic/developmental

35
Q

What is the role of lactose in pharmecuticals?

A

it is a common filler
people may think having a reaction to the drug itself, but really it is the lactose so you should see if atient is lactose intolerant first

36
Q

What are 3 broad categories of carbohydrate/sugar modifications

A

sugar alcohols, acidic sugars, and amino sugars

37
Q

What are sugar alcohols formed by and where does this occur?

A

formed by reduction of the carbonyl group

occurs in the polyol pathway

38
Q

Sorbitol

A
  • effective osmole

- used for storage in celll and can be metabolized forward to fructose or back to glucose

39
Q

Inositol

A
  • utilized in signaling, myelin attachment, and nerve function
  • cyclicAMP, PIP2
40
Q

What type of relationship is between sorbitol and inositol

A

inverse relationship

- as one increases, the other decreases

41
Q

inositol is an isomer of…

A

sorbitol

42
Q

what happens when you get an increase in sorbitol?

A

the cell brings in water and osmotic pressure increases, you have to regulate it because you do not want too much

43
Q

Two ways glucose is transported into the cell

A
  • insulin independent proteins

- insulin dependent proteins

44
Q

insulin-independent transporter proteins maintain…

A

the basal level of glucose required for cell survival

45
Q

What happens to excess glucose

A

it enters the polyol pathway

46
Q

What has a high percentage of insulin-independent transporters?

A

kidney, retinal, nerve tissue

47
Q

Which proteins can be upregulated insulin-dependent proteins or insulin-independent proteins?

A

insulin-dependent proteins

48
Q

When you raise the amount of glucose in the blood you get lots of _________ in the liver

A

insulin-dependent transport proteins

49
Q

Which transport proteins can not be upregulated

A

insulin-independent transport proteins

50
Q

How can you get an increase in insulin-independent transport proteins?

A

you are pulling in sugar at the basal level, but when you increase BP cells pull in more sugar than they can handle
- the excess sugar goes to the polyol pathway

51
Q

How are acidic sugars formed?

A

the oxidation of the 6’ OH group or the 1’ carbonyl group to a carboxyl group

52
Q

Where does the modification to acidic sugars occur?

A

many tissues, but highest in the liver, kidneys, RBCs

53
Q

Example of an acidic sugar

A

glucuronic acid

54
Q

Glucuronic acid

A

detoxifying agent

- conjugates with molecules to increase solubility and transport or excretion

55
Q

What is a byproduct of RBC and what does it do?

A

bilirubin

  • it is broken down by hemoglobin and the liver will conjugate it
  • conjugation increases solubility
56
Q

How are amino sugars formed?

A

the replacement of an OH group with an NH2

57
Q

2 examples of amino sugars

A

glucosamine and galactosamine

58
Q

What do glucosamine and galactosamine create?

A

the matrix in the connective tissue

59
Q

What increases the structural nature in amino sugars?

A

beta bonds between alternating sugars

60
Q

2 more examples of amino sugars

A

hyaluronic acid and chondroitin sulfate

61
Q

hyaluronic acid - amino sugar

A

least crosslinked, weakest, more fluid

- connective tissue in the skin

62
Q

chondroitin sulfate

A

more cross linked

63
Q

glucosamine and chondroitin sulfate are used for?

A

supplements in joints
- CARTILAGE in joints
cartilage is imbedded with calcium phosphate to get bone but the fibers made from amino sugars are more alkaline

64
Q

Purpose of the glycosylation of proteins (6)

A
  • modify/regulate protein function
  • stabilize proteins in the serum
    Fc fragment in antibodies - makes live longer
  • initial protein folding
  • cell recognition and binding to membrane proteins (blood types, inositol as second messenger)
  • increased hydration of molecule (mucous)
  • involved in stabilizing structure (connective tissue)
65
Q

Glycoprotein vs proteoglycan

A

proteoglycans are more protein than sugar, glycoproteins are more sugar than protein

66
Q

Proteoglycans

A

subset of glycoproteins

  • mainly found in connective tissue (chondroitin)
  • higher in protein content (85% vs 50% in glycoproteins)
67
Q

How can the glycosylation be categorized (2 ways)

A

N-linked or O-linked

68
Q

N-linked glycosylation

A

carbohydrate attaches to asparagine group

- deals with recognition, binding, stability (antibodies)

69
Q

O-linked glycosylation

A

attachment to a serine or threonine

- has diverse functions (mucins)