10017-07-9Relevant articles and documents
Synthesis of (R)-cyanohydrins by crude (R)-oxynitrilase-catalyzed reactions in micro-aqueous medium
Han, Shiqing,Lin, Guoqiang,Li, Zuyi
, p. 1835 - 1838 (1998)
In diisopropyl ether or ethyl acetate under micro-aqueous conditions, the enantioselective synthesis of (R)-cyanohydrins from aldehydes and methyl ketones was studied using crude (R)-oxynitrilase prepared from almonds. This reaction system performed well
Immobilized hydroxynitrile lyases for enantioselective synthesis of cyanohydrins: Sol-gels and cross-linked enzyme aggregates
Cabirol, Fabien L.,Hanefeld, Ulf,Sheldon, Roger A.
, p. 1645 - 1654 (2006)
The hydroxynitrile lyases (HNLs) from Prunus amygdalus (paHNL), Manihot esculenta (MeHNL), and Hevea brasiliensis (HbHNL) were successfully immobilized in sol-gels. The cross-linked enzyme aggregate (CLEA) of HbHNL was also prepared. These immobilized enzymes and the commercial PaHNL- and MeHNL-CLEAs were employed for the enantioselective synthesis of cyanohydrins. The sol-gels were highly efficient at low catalyst loading and particularly stable towards the organic solvent (diisopropyl ether) and substrate/product deactivation. The stabilization effect was inconsistent for CLEAs of different HNLs and significant deactivation of PaHNL- and HbHNL-CLEAs in diisopropyl ether was observed. In contrast commercial MeHNL-CLEA proved to be a remarkably robust and efficient biocatalyst in diisopropyl ether.
Evaluation of guanabana (Annona muricata) seed meal as a source of (S)-oxynitrilase
Solis, Aida,Luna, Hector,Perez, Herminia I.,Manjarrez, Norberto
, p. 2351 - 2353 (2003)
Guanabana seed meal is a source of (S)-oxynitrilase which biocatalyzes the enantioselective addition of HCN to aromatic, heteroaromatic and α,β-unsaturated aldehydes to produce cyanohydrins.
Chemoenzymatic synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids and their application in the synthesis of an α-hydroxylated β-hexapeptide
Tromp, Reynier A.,Van der Hoeven, Michael,Amore, Alessia,Brussee, Johannes,Overhand, Mark,Van der Marel, Gijs A.,Van der Gen, Arne
, p. 1109 - 1112 (2001)
A chemoenzymatic and stereoselective synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids from 2-furaldehyde is described as well as their application, without prior hydroxyl protection, in the solid-phase synthesis of a novel completely α-hydroxylated β-hexapeptide.
A study of asymmetric hydrocyanation of heteroaryl carboxaldehydes catalyzed by (R)-oxynitrilase under micro-aqueous conditions
Chen, Peiran,Han, Shiqing,Lin, Guoqiang,Huang, Hao,Li, Zuyi
, p. 3273 - 3279 (2001)
A number of new optically active heteroaryl cyanohydrins have been prepared by hydrocyanation under micro-aqueous conditions catalyzed by almond meal (containing (R)-oxynitrilase). Substituent effects on the reaction are discussed. This micro-aqueous meth
A High-Throughput Screening Method for the Directed Evolution of Hydroxynitrile Lyase towards Cyanohydrin Synthesis
Zheng, Yu-Cong,Ding, Liang-Yi,Jia, Qiao,Lin, Zuming,Hong, Ran,Yu, Hui-Lei,Xu, Jian-He
, p. 996 - 1000 (2021/01/15)
Chiral cyanohydrins are useful intermediates in the pharmaceutical and agricultural industries. In nature, hydroxynitrile lyases (HNLs) are a kind of elegant tool for enantioselective hydrocyanation of carbonyl compounds. However, currently available methods for demonstrating hydrocyanation are still stalled at precise, but low-throughput, GC or HPLC analyses. Herein, we report a chromogenic high-throughput screening (HTS) method that is feasible for the cyanohydrin synthesis reaction. This method was highly anti-interference and sensitive, and could be used to directly profile the substrate scope of HNLs either in cell-free extract or fermentation clear broth. This HTS method was also validated by generating new variants of PcHNL5 that presented higher catalytic efficiency and stronger acidic tolerance in variant libraries.
Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications
Zheng, Yu-Cong,Xu, Jian-He,Wang, Hui,Lin, Guo-Qiang,Hong, Ran,Yu, Hui-Lei
supporting information, p. 1185 - 1193 (2017/04/13)
Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products. (Figure presented.).
