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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]
The pathways linking arginine, glutamate, and proline are bidirectional. Thus, the net utilization or production of these amino acids is highly dependent on cell type and developmental stage. Altered proline metabolism has been linked to metastasis formation in breast cancer. [1]
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 Hajos–Parrish–Eder–Sauer–Wiechert and Barbas-List [1] reactions in organic chemistry are a family of proline-catalysed asymmetric aldol reactions.. In the 1970s, two research groups discovered (and published) almost simultaneously their discoveries of two related intramolecular reactions: Zoltan Hajos and David Parrish at Hoffmann-La Roche [2] [3] and Rudolf Wiechert et al at ...
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 systematic name of this enzyme class is L-proline:NAD(P)+ 5-oxidoreductase. Other names in common use include proline oxidase, L-proline oxidase, 1-pyrroline-5-carboxylate reductase, NADPH-L-Delta1-pyrroline carboxylic acid reductase, and L-proline-NAD(P)+ 5-oxidoreductase. This enzyme participates in arginine and proline metabolism.
In this reaction, naturally occurring chiral proline is the chiral catalyst in an aldol reaction. The starting material is an achiral triketone and it requires just 3% of proline to obtain the reaction product, a ketol in 93% enantiomeric excess. This is the first example of an amino acid-catalyzed asymmetric aldol reaction. [16] [17]
Proline-rich protein PRCC is a protein that, in humans, is encoded by the PRCC gene. [ 5 ] [ 6 ] In a subset of papillary renal cell carcinomas , a t(X;1)(p11;q21) chromosome translocation has been repeatedly reported and is thought to be the cause of the cancer.
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