Is it possible to change the chirality of the amino acids? I understand such a process is called "stereoinversion".

Take a levorotatory amino acid and turn it into it's dextrorotatory counterpart (enantiomer, optical isomer).

Anyone tried to do that? Can a high temperature change the chirality of an amino acid for example?

Racemization is good enough for me. Changing the chirality of just a small amount of the total amino acids in the sample is good enough.

  • 1
    $\begingroup$ I think the answer to this question depends heavily on whether you looking for a stereospecific mechanism or just racemization. $\endgroup$
    – Zhe
    Mar 10 '17 at 22:03
  • $\begingroup$ A cursory search of chemexper reveals that enantiomers of at least some of the 20 main amino acids are commercially available. $\endgroup$
    – TAR86
    Mar 11 '17 at 9:28

Temperature is likely not going to work. To racemise something that has a chiral center, you need to break a bond: if you want to supply that much energy by heating, you are going to fry your molecule.

The easiest things to do are usually extraction of an acidic proton with a strong base, formation of a double bond involving the formerly chiral carbon, and then you go back to the initial form, but obtaining a racemate because the attack on the two sides of the double bond is equally likely.

  • $\begingroup$ If the base racemization methodology exists, it's probably documented in the literature. $\endgroup$
    – Zhe
    Mar 10 '17 at 23:54
  • $\begingroup$ I'm pretty sure it does. $\endgroup$
    – Anon
    Mar 11 '17 at 10:46

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