H. Lickefett et al., ENANTIOSEPARATION OF 5-MONOSUBSTITUTED HYDANTOINS BY CAPILLARY GAS-CHROMATOGRAPHY - INVESTIGATION OF CHEMICAL AND ENZYMATIC RACEMIZATION, Tetrahedron : asymmetry, 4(6), 1993, pp. 1129-1135
The chemical as well as the enzymatic racemization of R- and S-5-monos
ubstituted hydantoin derivatives play an important role in the chemoen
zymatic synthesis of optically pure D- or L-amino acids. To study thes
e reactions, specifically with 5-alkylhydantoins enantiomer-separation
by capillary gas chromatography, kis(2,6-di-O-methyl-3-O-pentyl)-gamm
a-cyclodextrin as a chiral stationary phase was used. It will be shown
that this method allows the sensitive and reproducible detection of a
wide range of substrates in a short time. Examples are given for the
chemical racemization of different 5-alkylhydantoins as well as for th
eir enzymatic racemization by a hydantoin racemase of Arthrobacter sp.
DSM 3745.