Synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide catalyzed with (R)-oxynitrilase from loquat seed meal.
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.
Huang
Shun-Rong
SR
Department of Biotechnology, South China University of Technology, Guangzhou, 510640, P.R. China.
Liu
Sen-Lin
SL
Zong
Min-Hua
MH
Xu
Ruo
R
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*
C477045:2-trimethylsilyl-2-hydroxyethylcyanide; D002021:Buffers; D009570:Nitriles; D012997:Solvents; D014297:Trimethylsilyl Compounds; C010833:acetone cyanohydrin; D000446:Aldehyde-Lyases; C021541:mandelonitrile lyase