This intermediate rearranges to form a Schiff base attached to putrescine, which is attacked by lysine to release putrescine product and reform PLP-bound ODC.
32.
The product formed is an imidazolin-4-one which can be either isolated as a diastereomers or be used to give a Schiff base via ring opening.
33.
In the early work, the cyclization was accomplished by heating the Schiff base without a solvent and the yields were very moderate ( below 30 % ).
34.
Lysine Residue 133 serves as the nucleophile and attacks the carbonyl group of 2-Keto-3-deoxy-6-phosphogluconate to form a protonated carbinolamine intermediate, also known as a Schiff base intermediate.
35.
The newly formed oxide is then twice protonated to form the Schiff base, which then undergoes keto-enol tautomerization before an 4-hydroxyquinoline, the final product of the Conrad Limpach synthesis.
36.
After Schiff base formation, the fourth hydroxyl group on the fructose backbone is then deprotonated by an aspartate residue ( aspartate 33 ), which results in an aldol cleavage.
37.
The changes provide rationales for how relaxation of the distorted retinal causes movements of water and protein atoms that result in vectorial proton transfers to and from the Schiff base.
38.
If the pK a were not perturbed downward, the lysine residue would remain protonated as an ammonium cation, making it unreactive for the nucleophilic addition necessary to form the Schiff base.
39.
Further research led to the isolation of an active site peptide sequence and identification of the active site lysine, Lys115, that is involved in the formation of the Schiff base intermediate.
40.
His research group has synthesized a number of Schiff base polymers and have developed new stationary phase for Gas Chromatography and sensitive Liquid Chromatography procedures for the determination of pesticide malathion.
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