106942-16-9Relevant academic research and scientific papers
Asymmetric acyloin condensation catalysed by phenylpyruvate decarboxylase. Part 2: Substrate specificity and purification of the enzyme
Guo, Zhiwei,Goswami, Animesh,Nanduri, Venkata B.,Patel, Ramesh N.
, p. 571 - 577 (2001)
Phenylpyruvate decarboxylase from Achromobacter eurydice was used to catalyse the asymmetric acyloin condensation of phenylpyruvate 1 with various aldehydes 2 to produce optically active acyloins PhCH2COCH(OH)R 3. The specific activity of the phenylpyruvate decarboxylase enzyme was increased by a factor of 332 after its purification. The molecular weight of the purified enzyme was shown to be 150 kDa by gel filtration chromatography, while SDS gel electrophoresis showed two sub-units with molecular weights of 90 and 40 kDa. The acyloin condensation yield decreased with increasing chain length for straight chain aliphatic aldehydes from 76% for acetaldehyde to 24% for valeraldehyde. The e.e.s of the acyloin products were 87-98%. Low yields of acyloin products were obtained with chloroacetaldehyde (13%) and glycoaldehyde (16%). Indole-3-pyruvate was a substrate of the enzyme and provided acyloin condensation product 3-hydroxy-1-(3-indolyl)-2-butanone 5 with acetaldehyde in 19% yield, while benzoylformate was not a substrate for the enzyme.
Microwave-assisted synthesis of α-hydroxy ketone and α-diketone and pyrazine derivatives from α-halo and α,α′-dibromo ketone
Utsukihara, Takamitsu,Nakamura, Hiroaki,Watanabe, Masashige,Akira Horiuchi
, p. 9359 - 9364 (2008/01/27)
A novel reaction of α-halo ketone (α-bromo and α-chloro ketone) with irradiation under microwave gave the corresponding α-hydroxyketone and pyrazine derivative in good yields. In the case of α,α′-dibromo ketone, α-diketone was obtained. This reaction affords a new, clean and convenient synthetic method for α-hydroxyketone, α-diketone, α-chloro ketone and pyrazine derivative.
ADDITION OF ORGANOMAGNESIUM REAGENTS TO CYANOHYDRIN-O-SILYL ETHERS: AN EFFICIENT AND FLEXIBLE SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED ACYLOINS
Gill, Melvyn,Kiefel, Milton J.,Lally, Deborah A.
, p. 1933 - 1934 (2007/10/02)
Acyloins are prepared in high yields via reaction between Grignard reagents and O-trimethylsilyl ethers of aldehyde cyanohydrins: the method is particularly useful for the preparation of discrete acyloins in which the substituens are unsymmetrically dispo
