Stereochemistry of hydrogen removal from the 'unactivated' C-3 position of 4-hydroxybutyryl-CoA catalysed by 4-hydroxybutyryl-CoA dehydratase.
(R)- and (S)-gamma-[3-(2)H(1)]butyrolactones have been synthesised from (R)- and (S)-glycidol, respectively, and used to demonstrate that it is the pro-(S) hydrogen atom that is stereospecifically abstracted from C-3 of 4-hydroxybutyryl-CoA by 4-hydroxybutyryl-CoA dehydratase, and that this atom is not returned to C-4.
Scott
Richard
R
School of Natural Sciences - Chemistry, University of Newcastle upon Tyne, Bedson Building, Newcastle upon Tyne, UK.
Näser
Ulrike
U
Friedrich
Peter
P
Selmer
Thorsten
T
Buckel
Wolfgang
W
Golding
Bernard T
BT
D002384:Catalysis; D006836:Hydro-Lyases / Q000032:analysis / Q000737:chemistry*; D006859:Hydrogen / Q000032:analysis / Q000737:chemistry*; D008968:Molecular Conformation
D006859:Hydrogen; C066370:4-hydroxybutyryl-CoA dehydratase; D006836:Hydro-Lyases