title: Synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide catalyzed with (R)-oxynitrilase from loquat seed meal.
abstract: The synthesis of optically active (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide by asymmetric trans-cyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system was achieved using (R)-oxynitrilase from loquat seed meal. Diisopropyl ether was the most suitable organic phase among the organic solvents examined. The optimal concentration of acetyltrimethylsilane, concentration of crude enzyme, volume ratio of the aqueous to the organic phase, temperature and the buffer pH value were 14 mM: , 61.4 U ml-1, 13% (v/v), 30 degrees C and 4, respectively. The substrate conversion and the product enantiomeric excess were 95% and 98% under the optimized conditions. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon counterpart.
authors.affiliation: Department of Biotechnology, South China University of Technology, Guangzhou, 510640, P.R. China.
authors.forename: Shun-Rong
authors.initials: SR
authors.lastname: Huang
authors.forename: Sen-Lin
authors.initials: SL
authors.lastname: Liu
authors.forename: Min-Hua
authors.initials: MH
authors.lastname: Zong
authors.forename: Ruo
authors.initials: R
authors.lastname: Xu
mesh_terms: D000446:Aldehyde-Lyases / Q000737:chemistry / Q000378:metabolism*; D001671:Biochemistry / Q000379:methods; D001709:Biotechnology / Q000379:methods*; D002021:Buffers; D002384:Catalysis; D031983:Eriobotrya / Q000201:enzymology*; D006863:Hydrogen-Ion Concentration; D009570:Nitriles / Q000138:chemical synthesis / Q000378:metabolism*; D012639:Seeds / Q000201:enzymology; D012997:Solvents / Q000737:chemistry; D013379:Substrate Specificity; D013696:Temperature; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000378:metabolism*
chemical_list: C477045:2-trimethylsilyl-2-hydroxyethylcyanide; D002021:Buffers; D009570:Nitriles; D012997:Solvents; D014297:Trimethylsilyl Compounds; C010833:acetone cyanohydrin; D000446:Aldehyde-Lyases; C021541:mandelonitrile lyase