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CHEM191 > Module 4 > Flashcards

Module 4 Flashcards

1
Q

Alcohols

A

Undergo nucleophilic substitution
Can be oxidised
Form esters with carboxylic acids
Primary oxidised to aldehydes then carboxylic acid
Secondary oxidised to ketone
Tertiary not readily oxidised

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2
Q

Ethers and esters

A

Ethers may be cleaved but are generally unreactive
Esters are more easily cleaved by reaction with nucleophiles

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3
Q

Amides

A

Not basic or nucleophilic
Acid derivates, can react with nucleophiles such as water but not very reaction

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4
Q

Addition reaction of aldehyde and ketone with strong nucleophile

A

Nucleophile attacks in first step (rate determining)
Electrophile attacks in second step (fast)

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5
Q

Aldehydes vs Ketones

A

Aldehydes are more reactive than ketones
C of ketone is less attractive to nucleophiles
Aldehydes are less stericly hindered

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6
Q

Hemiacetal

A

R-OH
R-OR
Carbohydrates
Reducing sugar

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7
Q

Acetal

A

R-OR
R-OR
Complex carbohydrates
Non-reducing sugar

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8
Q

Addition of amino compounds

A

R-NH2 stronger nucleophile than ROH, as the lone pair of electrons on nitrogen are much loosely held and easily shared
Strong nucleophile

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9
Q

Fischer projection

A

Highest oxidised carbon at the top (i.e. CHO)
The longest carbon chain is the vertical bonds
Bonds up and down are into the page - -
Bonds to the side are out of the page —

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10
Q

Fischer projection D orientation

A

If the non-hydrogen atom (usually OH or NH2) is pointing to the right = D

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11
Q

Fischer projection L orientation

A

If the non-hydrogen atom (usually OH or NH2) is pointing to the left = L

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12
Q

Aldoses - size

A

Varying number of carbons
As no. of carbons increase, no. of chiral carbons and no. of stereoisomers increases
2^n (e.g. 2^4 = 16)

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13
Q

Cyclic hemiacetal

A

Molecule contains C=O and OH

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14
Q

Anomeric carbon

A

C atom bonded to two O atoms

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15
Q

Furanose

A

4 x C
1 x O
5 member ring

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16
Q

Pyranose

A

5 x C
1 x O
6 member ring

17
Q

Glucose

A

One of the most abundant monosaccharides
Found in alpha-D-glucopyranose and beta-D-glucopyranose

18
Q

B-D-glucopyranose

A

The D has a CH2OH group pointing up at C5 and an OH group pointing down at C1 (anomeric carbon)
Beta = same side

19
Q

a-D-glucopyranose

A

CH2OH pointing up at C1 (anomeric carbon), OH pointing down
One side up one side down = alpha

20
Q

Sucrose

A

D-glucose is in pyronose form
D-fructose is in furanose form

21
Q

Most reactive to least reactive

A

Acid chloride —> acid anhydride —> ester —> carboxylic acid —> tertiary amide —> secondary amide —> primary amide

22
Q

Why are amides least reactive?

A

C-N bond has partial double bond character (shorter than single bond, harder to break)

23
Q

How to calculate pI

A

Half way between pKa molecules closest in value
Find average (add together, divide by 2)

24
Q

Nucleosides

A

Combination of a sugar unit with a purine or pyrimidine base
Base attached to sugar at C-1 in the B-orientation

25
Q

Nucleotides

A

Phosphate derivatives
Connected to 5’ position of sugar
Heterocyclic base is attached to the C-1 sugar unit in the B position

26
Q

RNA vs DNA hydrolysis

A

RNA hydrolyses much faster than DNA due to the alcohol group electrons bonding to phosphate causing phosphate to have too many bonds, hence phosphate will break the bond causing chain of nucleotides to separate = RNA less stable

27
Q

NAD+ in molecules

A

Derived from ribose
Aromatic
Contains an amide functional group
No phosphate monoester

28
Q

Imine formation

A

Imine formation is reversible and water is produced as a by product

29
Q

In carboxypeptidase when zinc hydrolyses the amide bond what happens?

A

The side chain of the C-terminal amino acid sits in a hydrophobic binding pocket which presents the peptide bond to the active site
The zinc in the active side makes C=O bond of the peptide more susceptible to hydrolysis
The zinc activates a water molecule at the active site to assist in hydrolysis

30
Q

What is the source of energy behind the ATP molecule

A

The energy is released when a phosphoanhydride bond of ATP is broken
ATP is negatively charged at physiological pH and repels nucleophiles

31
Q

What metal ions complexes with cellular ATP in order that nucleopilic substitution reactions proceed rapidly

A

Magnesium

32
Q

Ala-Gly groups protected

A

On ala : amino group
On Gly : carboxylic acid group

CHEM191 (4 decks)

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