SLIDE 1
A biochemical way to oxidize alcohols: Alcohol dehydrogenase H H H - - PowerPoint PPT Presentation
A biochemical way to oxidize alcohols: Alcohol dehydrogenase H H H - - PowerPoint PPT Presentation
A biochemical way to oxidize alcohols: Alcohol dehydrogenase H H H + ENZ :B ENZ H NAD + NAD + + + + H B H 3 C O H 3 C O H R + N H 2 N O H H H 3 C O H : B Enzyme The enzyme, :BENZ, has a basic functional group in
SLIDE 2
SLIDE 3
There also is a binding site for NAD+
N
+
R N H2 O B Enzyme :
SLIDE 4
When the alcohol binds in the acitve site of the enzyme, an elimination reaction can proceed
N
+
R N H2 O C H3 O H H H B Enzyme :
SLIDE 5
Deprtonation by the base
N
+
R N H2 O C H3 O H H H B Enzyme :
SLIDE 6
allows for C=O double bond formation
N
+
R N H2 O C H3 O H H H B Enzyme :
SLIDE 7
the formal leaving group is H-, a hydride, which can be added to NAD+
N
+
R N H2 O C H3 O H H H B Enzyme :
SLIDE 8
with allylic rearrangement of the pi electon system
N
+
R N H2 O C H3 O H H H B Enzyme :
SLIDE 9
to quench the formal positive change of nitrogen . . .It’s an E2-type elimination reaction!
N
+
R N H2 O C H3 O H H H B Enzyme :
SLIDE 10