Reaction #502066

Reaction equation

phenyllactic acid

phenylglycine

2-chloromandelic acid

→

(S)-phenyllactic Acid

Conditions

Workup

1. 1
   ConcentrationHowever, in this case, adjustment of the solvent concentration in the nonchiral HPLC method
2. 2
   OtherRepresentative nonchiral chromatograms of the product (1.9 min) and cyanohydrin substrate (3.7 min)
3. 3
   Otherat 6 min.

Procedure

The analysis of phenyllactic acid was initially plagued with the same problems discussed for phenylglycine and 2-chloromandelic acid. However, in this case, adjustment of the solvent concentration in the nonchiral HPLC method led to a shift in the retention time of the acid, so that it no longer coeluted with the cell lysate peak. Following this, no problems were encountered with either the nonchiral or chiral methods. Representative nonchiral chromatograms of the product (1.9 min) and cyanohydrin substrate (3.7 min) are shown in FIG. 8A, while the chiral analysis of the acid is shown in FIG. 8B, with the L-enantiomer eluting at 2 min and the opposite enantiomer at 6 min.

Source