10021-63-3Relevant articles and documents
Difficult substrates in the R-hydroxynitrile lyase catalyzed hydrocyanation reaction: Application of the mass transfer limitation principle in a two-phase system
Gerrits, Pieter J.,Marcus, Jan,Birikaki, Lemonia,Van der Gen, Arne
, p. 971 - 974 (2001)
The application of a number of new and/or difficult substrates in the catalyzed hydrocyanation reaction by R-hydroxynitrile lyase from almonds is described. By using an aqueous-organic two-phase system and increasing the rate of the enzymatic reaction relative to the mass transfer rate, the enantiomeric purity was improved. By fine tuning the reaction parameters (temperature, pH, and the amount of enzyme) the hydrocyanation reaction was optimized for all substrates. The general principles described here can also be applied to optimize the reaction conditions for other substrates.
Enzymatic Resolution of Optically Active Aliphatic Cyanohydrins
Kanerva, Liisa T.,Kiljunen, Eero,Huuhtanen, Tuomas T.
, p. 2355 - 2362 (1993)
Enantioselective acylation of cyanohydrins 1a-9a by PPL catalysis and deacylation of propionates 1b-9b by CCL catalysis in toluene from good (E 15-20) to excellent (E >30) enantioselectivity.A solvent has a clear effect on enzymatic enantioselectivity.
A simple separation method for (S)-hydroxynitrile lyase from cassava and its application in asymmetric cyanohydrination
Zheng, Zubiao,Zi, Yan,Li, Zhongzhou,Zou, Xinzhuo
, p. 434 - 439 (2013/06/27)
Using an acetone precipitation method, crude (S)-hydroxynitrile lyase [(S)-MeHNL] was separated from Munihot esculenta (cassava) leaves, and used directly as biocatalyst to catalyze asymmetric cyanohydrination and produce cyanohydrins with enantiomeric purities (≥90% ee) significantly greater than those previously reported. The use of a water/i-Pr2O system with an enzyme, NaCN, and appropriate amounts of acetic acid is crucial in improving the stereoselectivity of cyanohydrin formation by minimizing the non-enzymatic reaction and the racemization of the chiral products. The proposed isolation method for crude (S)-MeHNL has a high value because of its simplicity, and low cost as well as the high activity of the crude (S)-MeHNL.
Stereoselective synthesis of β-amino-γ-butyrolactones
Roos, Juergen,Effenberger, Franz
, p. 1855 - 1862 (2007/10/03)
A novel synthesis of optically active β-amino-γ-butyrolactones is described. O-Silylated (R)-cyanohydrins (R)-3 (derived from aldehydes 1 by (R)-hydroxynitrile lyase ((R)-PaHNL)-catalyzed addition of HCN) were reacted with allyl Grignard to give amino alc