(R)-oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins.
Optically active 2-trimethylsilyl-2-hydroxyl-ethylcyanide was prepared by enzymatic enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system at 35 degrees C and pH 5. (R)-Oxynitrilase from apple seed meal was the best among all the enzymes explored and diisopropyl ether was the most suitable organic phase. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon analogue. The substrate conversion and product enantiomeric excess of 2-trimethylsilyl-2-hydroxyl-ethylcyanide were >99% and >99%, respectively.
Li
Ning
N
Biotechnology Department, South China University of Technology, Guangzhou 510640, PR China.
Zong
Min-Hua
MH
Liu
Chen
C
Peng
Hua-Song
HS
Wu
Hua-Chang
HC
D000446:Aldehyde-Lyases / Q000737:chemistry*; D002384:Catalysis; D006863:Hydrogen-Ion Concentration; D007659:Ketones / Q000737:chemistry; D027845:Malus / Q000737:chemistry / Q000201:enzymology; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry / Q000201:enzymology; D012825:Silicon / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
C477045:2-trimethylsilyl-2-hydroxyethylcyanide; D007659:Ketones; D009570:Nitriles; D014297:Trimethylsilyl Compounds; C477044:acetyltrimethylsilane; C430593:cyanohydrin; C010833:acetone cyanohydrin; D000446:Aldehyde-Lyases; C021541:mandelonitrile lyase; D012825:Silicon