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AQA A Level Chemistry Amino acids

How do you know that 2,6-diaminohexanoic acid has a basic side chain please? And do any other amino acids have it
Original post by anon25x
How do you know that 2,6-diaminohexanoic acid has a basic side chain please? And do any other amino acids have it

Amino acids have the general formula NH2CHRCOOH, where R is the side chain.

In this case, R is CH2CH2CH2CH2NH2.

The nitrogen in the NH2 on the side group has a lone pair, so it can accept H^+ ions- that implies the side chain is basic.

Of course there are other amino acids with basic side chains, but you’ll have to try to spot functional groups like -NH2 to work out whether they have basic side chains or not.
Well it’s got an amine on its side chain with a lone pair, which at physiological pH is going to be protonated. And yes - Arginine and Histidine also have basic side chains.
Reply 3
Original post by TypicalNerd
Amino acids have the general formula NH2CHRCOOH, where R is the side chain.

In this case, R is CH2CH2CH2CH2NH2.

The nitrogen in the NH2 on the side group has a lone pair, so it can accept H^+ ions- that implies the side chain is basic.

Of course there are other amino acids with basic side chains, but you’ll have to try to spot functional groups like -NH2 to work out whether they have basic side chains or not.


Original post by Max1357913
Well it’s got an amine on its side chain with a lone pair, which at physiological pH is going to be protonated. And yes - Arginine and Histidine also have basic side chains.

I think I get it now so if an amino acid has a COOH group where the R group usually is then its sidechain is acidic if it has an NH2 in place of the R group the side chain is basic?Also thank you both for replying so quickly !
Original post by anon25x
I think I get it now so if an amino acid has a COOH group where the R group usually is then its sidechain is acidic if it has an NH2 in place of the R group the side chain is basic?Also thank you both for replying so quickly !

Correct.

Well, I wouldn’t say ‘in the place of’, I’d say ‘on’ the side chain.
(edited 1 year ago)
Original post by anon25x
I think I get it now so if an amino acid has a COOH group where the R group usually is then its sidechain is acidic if it has an NH2 in place of the R group the side chain is basic?Also thank you both for replying so quickly !


Essentially, but it’s not ‘in place of’ the R group, it IS the R group - ‘R’ is just generic to say ‘this is not the end of the structure - a thing goes here’. It’s also worth pointing out that one unusual amino acid is cysteine, which has a thiol (SH) as it’s R group, which is slightly acidic.
(edited 1 year ago)

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