Self-disproportionation of N-acetyl-dl-phenylalanine

[Maniek]

HI!
I need information on the self-disproportionation of N-acetyl-dl-phenylalanine on achiral - phase chromatography columns . I am looking for publications in which is described the change of optical purity e.e?

 

[TeethWhitener]

I can't find anything with a cursory glance over the literature specifically for N-acetylphenylalanine. There may be a few reasons for this. It's my understanding that 1) you have to have some enantiomeric excess to begin with, and 2) the effect depends strongly on how different functional groups affect aggregation of the molecules in solution. So if you just start with pure N-acetyl-DL-phenylalanine (a racemic mixture), you presumably won't get any effect. But it might also be the case that even for a non-racemic mixture of N-acetylphenylalanine, the individual molecules simply don't aggregate properly to see a strong effect. Here's a review article:

http://pubs.rsc.org/en/Content/ArticleLanding/2012/CS/C2CS35006H#!divAbstract