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Medicinal Chemistry > Chirality 1 & 2 > Flashcards

Chirality 1 & 2 Flashcards

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1
Q

What are stereoisomers?

A

Isomers with same molecular formula + same connectivity of atoms BUT different spatial arrangement

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2
Q

Describe constitutional isomerism

A

Molecules with same formula but different connectivity

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3
Q

What can constitutional isomers not do?

A

Interconvert

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4
Q

What are examples of constitutional isomers?

A

Aspirin
Caffeic acid
4-hydroxyphenyl-pyruvic acid

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5
Q

What is geometric isomerism?

A

Cis + trans

Same formula, same connectivity of C skeleton but different spatial arrangement of substituents around alkane

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6
Q

What is cis?

A

Same face

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7
Q

What is trans?

A

Opposite faces

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8
Q

When is there no interconversion between cis + trans?

A

At ambient or body temp

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9
Q

What temp is required for cis + trans interconversion?

A

180 degrees

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10
Q

What is the cis form of C4H4O4?

A

Maleic acid

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11
Q

What is the trans form of C4H4O4?

A

Fumaric acid

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12
Q

What is the Cahn-Ingold-Prelog naming system?

A

Prioritise 2 substituents according to their atomic number of atom directly attached to C

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13
Q

What is it if priority groups 1 are on same face?

A

Z

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14
Q

What is it if priority groups 1 are on opposite faces?

A

E

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15
Q

What does stereoisomers normally have?

A

Chiral C

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16
Q

What is a chiral carbon?

A

Stereocentere = stereogenic C

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17
Q

What is optically inactive?

A

Achiral

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18
Q

What is a racemic mixture?

A

1:1 mix of enantiomers

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19
Q

What happens if it is a mirror image?

A

Non-superimposable

20
Q

What is hybridisation state of chiral C?

A

sp3

21
Q

If it is superimposable what it is?

A

Achiral

22
Q

if it is non-superimposable what it is?

A

Chiral

23
Q

What is the non-superimposable mirror image called?

A

Enantiomers

24
Q

What can a carbohydrate be?

A

D or L

25
Q

If the OH in a carbohydrate is to the left, what is it?

A

L

26
Q

If the OH in a carbohydrate is to the right, what is it?

A

D

27
Q

Can amino acids be D or L?

A

YES

28
Q

What are most amino acids in proteins?

A

L

29
Q

How do you determine of an amino acid is L or D?

A

Position of amine group

30
Q

How do you use Cahn-Ingold-Prelog naming system for chiral C?

A

Prioritise groups around C with lowest priority going away from you

31
Q

If Cahn-Ingold-Prelog naming system for chiral is clockwise order what do you name it?

A

R

32
Q

If Cahn-Ingold-Prelog naming system for chiral is anti-clockwise order what do you name it?

A

S

33
Q

What is the dashed line mean in drawing out chiral C?

A

Group is behind C

34
Q

What happens if priority 4 is at the front instead?

A

Viewing molecule from opposite side
= reverse answer
= clockwise really anti-clockwise

35
Q

What must we do if priority 4 is not at the back?

A

Must rotate molecule

36
Q

What do R + S isomers of a molecule have?

A

Identical physical + chemical properties

37
Q

How is plane polarised light produced?

A

By passing light through polarising filter

38
Q

What does each optically active compound have?

A

Character specific rotation

39
Q

What is a racemic mixture than contains equal amount of 2 enantiomers?

A

Optically inactive

40
Q

What is enantiomer excess (ee)?

A

Amount of enantiomer in excess of racemic mixture

41
Q

What happens if ee is 50%?

A

Then the observed rotation will only be 50% of the rotation of the pure enantiomer

42
Q

How can ee be calculated?

A

Observed specific rotation
—————————————————- X100
specific rotation of pure enantiomer

43
Q

What do R enantiomers do?

A

Bind correctly = trigger response

44
Q

What do S enantiomers do?

A

Cannot bind correctly = do not trigger response

45
Q

Describe Vigabatrin

A

S-enantiomer active as anti-convulsant
Inhibits inactivation of GABA by GABA transaminase
Increases levels of GABA = reduces seizures

46
Q

How do you name when more than 1 stereogenic centre?

A

Number the S + R centre

47
Q

What happens if the molecule has an internal plane of symmetry?

A

Meso compound

Medicinal Chemistry (19 decks)

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