Biocatalytic deuterium- and hydrogen-transfer using over-expressed ADH-'A': enhanced stereoselectivity and 2H-labeled chiral alcohols.
Employing the over-expressed highly organic solvent tolerant alcohol dehydrogenase ADH-'A' from Rhodococcus ruber DSM 44541, versatile building blocks, which were not accessible by the wild type catalyst, were obtained in > 99% e.e.; furthermore, employing d8-2-propanol as deuterium source, stereoselective biocatalytic deuterium transfer was made feasible to furnish enantiopure deuterium labeled sec-alcohols on a preparative scale employing a single enzyme.
Edegger
Klaus
K
Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz, Austria.
Gruber
Christian C
CC
Poessl
Tina M
TM
Wallner
Sabine R
SR
Lavandera
Iván
I
Faber
Kurt
K
Niehaus
Frank
F
Eck
Juergen
J
Oehrlein
Reinhold
R
Hafner
Andreas
A
Kroutil
Wolfgang
W
D000426:Alcohol Dehydrogenase / Q000096:biosynthesis / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003903:Deuterium / Q000737:chemistry*; D004926:Escherichia coli; D005240:Feasibility Studies; D006859:Hydrogen / Q000737:chemistry*; D007553:Isotope Labeling / Q000379:methods; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012240:Rhodococcus / Q000201:enzymology; D013237:Stereoisomerism
D000438:Alcohols; D007659:Ketones; D006859:Hydrogen; D003903:Deuterium; D000426:Alcohol Dehydrogenase