Sciencemadness Discussion Board

hydrolysis of theanine to produce ethylamine

SunriseSunset - 5-9-2015 at 02:27

So I've found that:

Thaenine and Glutamine both are hydrolyzed to Glutamic acid and produce ethylamine and ammonia by certain enzymes within the body.

Anybody have any ideas which catalysts may be used in place of an enzyme for lab practicality?

Glutamine + H2O + enzyme -> Glutamic acid + NH3

Theanine + H2O + enzyme -> Glutamic acid + Ethylamine

Thanks

[Edited on 5-9-2015 by SunriseSunset]

kecskesajt - 5-9-2015 at 03:24

After a short googleing, I found out that theanine has a low stablility in alkaline conditions.

UC235 - 5-9-2015 at 06:53

Given the cost of theanine online and it's considerable molar mass compared to ethylamine, you're probably much better off using a Hofmann rearrangement on propanamide. Calcium propionate is very cheap and used as a food additive.

If you insist on using theanine, heating with ~2 1/2 equivalents of KOH or NaOH and as little water as possible would probably be the way to go. The ethylamine will be expelled as a wet gas and should be collected by absorption into ice water with a suckback trap.

[Edited on 5-9-2015 by UC235]