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Proline organocatalysis is the use of proline as an organocatalyst in organic chemistry. This theme is often considered the starting point for the area of organocatalysis, even though early discoveries went unappreciated. [1] Modifications, such as MacMillan’s catalyst and Jorgensen's catalysts, proceed with excellent stereocontrol. [2]: 5574 [3]
Proline and its derivatives are often used as asymmetric catalysts in proline organocatalysis reactions. The CBS reduction and proline catalysed aldol condensation are prominent examples. In brewing, proteins rich in proline combine with polyphenols to produce haze (turbidity).
The CBS catalyst or Corey–Bakshi–Shibata catalyst is an asymmetric catalyst derived from proline. It finds many uses in organic reactions such as the CBS reduction, Diels-Alder reactions and (3+2) cycloadditions. Proline, a naturally occurring chiral compound, is readily and cheaply available.
The original Hajos-Parrish procedure begins with an achiral triketone in dimethylformamide and 3% (molar) catalytic (S)‑(−)‑proline. The product is a chiral ketol with 93% enantiomeric excess: In the Eder-Sauer-Wiechert modification, the product shown above loses water to give the conjugated alkene.
The stereoisomer (S)-1-pyrroline-5-carboxylate (also referred to as L-P5C) is an intermediate metabolite in the biosynthesis and degradation of proline and arginine. [ 4 ] [ 5 ] [ 6 ] In prokaryotic proline biosynthesis, GSA is synthesized from γ-glutamyl phosphate by the enzyme γ-glutamyl phosphate reductase .
The 3 substrates of this enzyme are L-proline, 2-oxoglutarate, and O 2, whereas its 3 products are cis-3-hydroxy-L-proline, succinate, and CO 2. This enzyme belongs to the family of oxidoreductases , specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen.
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The biochemical mechanism of proline racemase was first put forward in the late sixties by Cardinale and Abeles [6] using the Clostridium sticklandii enzyme, CsPRAC. The catalytic mechanism of proline racemase was late revisited by Buschiazzo, Goytia and collaborators that, in 2006, resolved the structure of the parasite TcPRAC co-crystallyzed with its known competitive inhibitor - pyrrole ...
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