Reaction #1795522

ord-5a3315f753544f339ffb135924df35b0

Reaction equation

OO
hydrogen peroxide
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
C=CC=C
1,3 butadiene
C=CC=C
1,3-butadiene
→
C=CC1CO1
butadiene monoxide
C/C=C/C=O
crotonaldehyde

Reactants

OO
hydrogen peroxide
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
C=CC=C
1,3 butadiene
C=CC=C
1,3-butadiene

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Elfarra et al. (1991 Arch. Bioch. Biophy. 286, 244-251) has demonstrated the NADPH-dependent oxidation of 1,3-butadiene by mouse liver microsomes and the hydrogen peroxide-dependent oxidation of 1,3 butadiene by chloroperoxidase. Both oxidations yielded butadiene monoxide and crotonaldehyde.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05358860uspto-grants-1994_10