Another study demonstrates how racemic nicotine (mixture of S and R-enantiomers 1 in scheme 3) can be deracemized in a one-pot procedure involving a monoamine oxidase isolated from Aspergillus niger which is able to oxidize only the amine S-enantiomer to the imine 2 and involving an ammonia–borane reducing couple which can reduce the imine 2 back to the amine 1.
The substances are prepared via a Knoevenagel condensation of a thiohydantoin–phenylalanine imine with different aldehydes, which yields a mixture of E and Z isomers.
The overall pathway of glucosepane formation starts with lysine attacking the reducing sugar D-glucose to form the unstable imine known as a Schiff base, which then rearranges to form the more stable aminoketose Amadori product.