Jump to content

Enzymatic synthesis of Beta-aminoisobutyric acid


Recommended Posts

Hello all, so for a project I need to think of a pathway to produce (R)-beta-3-aminoisobutyric acid (BAIBA), starting from either proteinogemic amino acids or glycolysis intermediates. So far I have settled on either using pyruvate or L-valine. From L-valine it is quite well known how to get the S isomer of BAIBA , but not how to get to the R enantiomer from this.

So for now my sights are set on pyruvate. I can't find too much literature where enzymes are used for this, but are there any enzymes that could help attach an ethyl amine to the carbonyl center and then let the remaining hydroxyl leave as a water? Then a kinetic resolution could be used to obtain pure R-isomer.

Or maybe I am going on this in a way to round about way and you know have a way better idea. So what are your ideas on this? I could really use another perspective for some inspiration.

afbeelding.png.894b12b6244b8087227a8019153d32b4.png

Link to post
Share on other sites

On your reactant side there are a total of five carbons, and on your product side, there are four carbons.  Also when an amine adds into a ketone or aldehyde, one obtains an imine.  There would have to be a reduction to obtain an amine.  I have no idea what the ideal solution is, but I might be tempted to look for amino acids or common metabolic intermediates that have the same number of carbon atoms.  With respect to the route I suggested or with respect to valine, I would also look into various kinds of known racemase, epimerase, or mutase reactions.

Link to post
Share on other sites

Create an account or sign in to comment

You need to be a member in order to leave a comment

Create an account

Sign up for a new account in our community. It's easy!

Register a new account

Sign in

Already have an account? Sign in here.

Sign In Now
×
×
  • Create New...

Important Information

We have placed cookies on your device to help make this website better. You can adjust your cookie settings, otherwise we'll assume you're okay to continue.