Amino acids, peptides and proteins Flashcards

1
Q

Amino acid

A

A class of organic compound with at least one amino group and one carboxyl group

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2
Q

Peptide

A

An organic compound formed from the linking of <= 50 amino acids

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3
Q

Peptides are written from their…

A

…N to C terminus.

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4
Q

Protein

A

Macromolecules consisting of one of more polypeptide chains linked via non-covalent or dithiane interactions

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5
Q

Functions of proteins

A

Enzymes
Transporters
Regulatory proteins

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6
Q

Conjugated proteins

A

Have additional groups that may or may not be covalently bound
e.g. glycoproteins, lipoproteins, nucleoproteins, metalloproteins

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7
Q

Secondary structure

A

Interactions between amino acids in the same polypeptide chain

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8
Q

Alpha-helix

A

H bond interactions between the carbonyl of one amino acid (i) and the amine of another amino acid (i+4)

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9
Q

Which amino acids disfavour alpha-helix formation?

A

Amino acids with bulky R groups e.g. V T I
Charged amino acids e.g. S D N
Glycine (flexible)
** Alpha-helices are broken by proline due to its locked structure **

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10
Q

Beta-sheet

A

H bonding of amino acids through space

Can be parallel or anti-parallel depending on the N–>C direction of the chains

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11
Q

Beta-turn

A

A number of short turns that cause beta-sheets to form through folding of peptide chains back on themselves
Usually involve 3 amino acids (i) and (i+3)

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12
Q

Tertiary structure

A

How all the polypeptide chains fold together to form the protein

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13
Q

Examples of tertiary structures

A

Coordination of metals
Disulfide bridges
Ionic interactions
Hydrophobic interactions e.g. Leucine zipper

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14
Q

Leucine zipper

A

= coiled-coil

The vdW interaction between a pair of amphipathic alpha-helices through their hydrophobic faces

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15
Q

Amphipathic

A

Having both hydrophilic and hydrophobic parts

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16
Q

Quaternary structure

A

Bringing together multiple subunits

Not held together by covalent bonds

17
Q

Why are acid chlorides not often used in peptide synthesis?

A

Due to potential racemisation via ketene formation

18
Q

DCC

A

Poorly soluble

Removed from reactions by filtration

19
Q

DIC

A

DCM-soluble
Removed by DCM-washes
Used in solid-phase chemistry

20
Q

EDC / ECI / WSC.HCl

A

Water-soluble

Removed by water washes

21
Q

Problems associated with solution-phase synthesis

A

Increasing the concentration of the reaction can increase the probability of side reactions
Adding excess reagent can lead to a mixture of products

22
Q

SPPS works…

A

…C–>N.

23
Q

Advantages of SPPS

A

The polymer is so large that it is less likely to self-react

Can be purified by filtration

24
Q

Main problem associated with SPPS

A

Cleavage of the peptide from the polymer

25
Q

Types of resin support

A

Polystyrene
Polyacrylamide
PEG-polystyrene

26
Q

Disadvantage of polystyrene

A

Hydrophobic - so is incompatible with polar solvents

27
Q

Example of a drug made by SPPS.

A

Enfuvitide (anti-HIV drug)

36 amino acids long