[Babcock_Hall]

A reviewer would like to know whether our novel amino acid salts RCH=CHCH₂CH(NH₂HCl)CO₂H] racemized during the synthesis.  They are soluble in water/acetonitrile during LC-MS experiments and generally soluble in DMSO.  Only one is UV-active, which might make detection in LC more difficult.  I doubt that they would be soluble in a chiral NMR solvent, but I don't know.  What sorts of methods should we be thinking about?
EDT
One person suggested making Mosher amides.

[rolnor]

Yes, Mosher amide would be a good idea, chiral solvents are not reliable, you might not get any separation of the peaks on NMR, a chiral column and LC would require that you have the two isomers and develop a method with a chiral column I guess.

[Babcock_Hall]

My concern with Mosher chemistry is that we have a free carboxylic acid in the molecule, which might react with the Mosher acyl chloride.

HPLC with a polysaccharide based stationary phase or with a chiral ion-pair reagent might work, but both of those are speculation on my part.  I am starting to search for examples.