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Biological chemistry CH10088 > lecture 1 > Flashcards

lecture 1 Flashcards

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1
Q

Definition of a curly arrow

A

Movement of a pair of electrons

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2
Q

Reduced structure

A
  • carbons omitted
  • hydrogen attached to carbons omitted
  • hydrogens attached to heteroatom stay
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3
Q

What is the definition of resonance

A

Movement of electrons

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4
Q

What is the definition of tautomerism

A

Movement of one or more double bonds and a small atom ( usually H)

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5
Q

what is the definition of conjugation?

A

alternating single and double bonds

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6
Q

What is conformation?

A

bond rotation , no bond breaking

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7
Q

What energy state is more stable, staggered or eclipsed?

A

staggered

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8
Q

What is the Phi angle rotation about?

A

Rotation about the N - C alpha bond

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9
Q

What is the Psi angle rotation about?

A

Rotation about the C alpha - CO bond

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10
Q

What is configuration?

A

Different configurations are obtained by bond breakage

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11
Q

What is the definition of chirality?

A

Chiral objects do not have an internal plane of symmetry

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12
Q

What form (R or S) are amino acids?

A

s

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13
Q

What are enantiomers?

A

non - superimposable , mirro images

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14
Q

What is a prochiral species?

A

has the potential to become chiral

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15
Q

What is an diastereomer?

A

Non superimposable, non mirror image

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16
Q

What is a meso compound?

A
  • Meso object is one that contains chiral parts but overall chiral (as it contains a plane of internal symmetry)
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17
Q

How do you work out the number of stereoisomers in a compound?

A

2^N , where N is the number of chiral centres

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18
Q

where is the cyanohydrin seen in nature?

A
  • millipedes

- reverse the reaction to get poison

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19
Q

What to remember for base catalysed semi-acetal formation?

A

you have to form the nucleophile first

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20
Q

What type of interaction is hydride transfer?

A

Soft - Soft interaction

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21
Q

How can you solve most of the problems with peptide synthesis?

A

Using DCC

22
Q

Advantages of solid phase synthesis

A

you can purify as you go

23
Q

Disadvantages of solid phase synthesis

A

You have to limit polypeptide length

24
Q

What happens to the water in the DCC reaction?

A

DCC locks up water in the peptide bond formation, driving equilibrium to RHS

25
Q

What molecules do you need for cyanohydrin formation?

A

NaCN and H30 plus

26
Q

What type of catalysis does acetal formation need? base or acid?

A

Acid only

27
Q

What are mine formation and acetal formations an example of?

A

Nucleophilic substitution with loss of carbonyl group’s oxygen

28
Q

Why is water a good leaving group?

A

Because its conjugate acid (H3O) has a low pKa

29
Q

What do you have to do to get from a hemiacetal to an acetal?

A

Kick the OH out and replace with an RO

30
Q

What is an example of an imine in nature?

A

In DNA , cytosine

31
Q

Which is more stable =, the enol or the ketone?

A

The ketone, enols are generally unstable

32
Q

What is an example of a stable enol?

A

phenol

33
Q

Which catalysis does enol formation have?

A

both - acid and base

34
Q

What is formed in the aldol reaction?

A

C-C bond formed

35
Q

What type of catalysis is the aldol reaction?

A

acid - catalysed

36
Q

What two components are needed in the aldol reaction?

A

An enol and an aldehyde

37
Q

What are esters reluctant to form?

A

enrols , but thiol esters are not

38
Q

What is an example of an aldol reaction in nature?

A

In the citric acid cycle.Converting Acetal CoA and oxaloacetate into citrate

39
Q

What role doe the oxaloacetate play in the aldol reaction?

A

The aldehyde

40
Q

What role does the acetyl - CoA play in the aldol reaction?

A

The enol

41
Q

What is The role of aspartic acid In citrate synthase ?

A

Take an H , is a base

42
Q

What is the role of Histidine in citrate synthase?

A

Acid and base

43
Q

how do you draw tautomerism?

A

The double bond arrow allows go the dashed line

44
Q

Where do bulky side group sit in a chair conformation?

A

On the equatorial bonds

45
Q

Why can something have a lower pka?

A

more conjugate bases, more stability

46
Q

Why are aldehydes more reactive than ketones?

A
  • Ketones have 2 stabilising effects where as aldehydes only have one which makes them more stable
47
Q

When determine the ionisation state, do you draw the arrow from the pKA or the pH?

A

Draw it from the pKA

48
Q

What must you remember when drawing chair conformers?

A

There are two conformers

49
Q

What makes a strong nucleophile?

A
  • Has a negative charge, weakly electronegative and large (polarisability)
50
Q

What do you have to remember with the 90 degree Psi rotations?

A

You can then see the double bond O

Biological chemistry CH10088 (18 decks)

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