Cytochrome P450-Catalyzed Insertion of Carbenoids into N-H Bonds.
Expanding nature's catalytic repertoire to include reactions important in synthetic chemistry will open new opportunities for 'green' chemistry and biosynthesis. We demonstrate enzyme-catalyzed insertion of carbenoids into N-H bonds. This type of bond disconnection, which has no counterpart in nature, can be mediated by variants of the cytochrome P450 fromBacillus megaterium. The N-H insertion reaction takes place in water, provides the desired products in 26-83% yield, forms the single addition product exclusively, and does not require slow addition of the diazo component.
Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd. MC-210-41 Pasadena, CA 91125.
Z Jane
ZJ
Wang
Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd. MC-210-41 Pasadena, CA 91125.
Nicole E
NE
Peck
Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd. MC-210-41 Pasadena, CA 91125.
Hans
H
Renata
Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd. MC-210-41 Pasadena, CA 91125.
Frances H
FH
Arnold