It's been a while since I've thought a ton about synthetic organic chemistry, so please for give my naivete.
For example, say I wanted to add an R group to the amine group on glycine. I believe that I could use a halogenated alkane, but I also think that the alkane would then add to the carboxylic acid.
I might be able to reason through a protection of the carboxylic acid.
But I wonder if modification of amines in a related way is more common than it seems from a perusing of the literature and thus if there is a well laid-out strategy (using halogenated precursors or other methods).
Thanks.
Hi
Reductive animation is the way to go for alkylating an amine.
The problem alkylation using a base and halogenated alkane is the increased likelihood of double alkylation which depending on your objective may or may not be what you want. You are right that the carboxylic acid most likely needs a protecting group but again depends on the alkyl group you want to put on. Many amino acids can be purchased as the esters and "saves" you the additional esterification step.
Bryan Spiegelberg
Hope you are doing well.
This question is really comprehensive owing to sensitive conditions of amino acids. Firstly and most importantly, as structures of these compounds act as both an acid and a base, the pH of the situation plays a crucial role in which amino acids can be converted into anionic and cationic forms. Secondly, reactions of amines depend on the type of amine group (primary or secondary) that, for alkylation, polymerization should be taken into account. Amine acylation through acylating reagents can be done but the nucleophilicity of nitrogen and carboxylate anions can compete in the reaction.
Best regards
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