Rule bt0243
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N-substituted Amide -> Amide + Aldehyde or Ketone
N, N-disubstituted Amide -> N-substituted Amide + Aldehyde or Ketone
N-substituted Urea derivative -> Urea derivative + Aldehyde or Ketone
N,N-disubstituted Urea derivative -> N-substituted Urea derivative + Aldehyde or Ketone
| Aerobic Likelihood: | | Neutral |
EAWAG-BBD Reaction(s):
Alachlor -----> Formaldehyde + 2-Chloro-2',6'-diethylacetanilide (reacID# r1677)
Caffeine -----> Paraxanthine (reacID# r1251)
Caffeine -----> Theobromine (reacID# r1247)
Diazepam -----> 7-Chloro-5-phenyl-3H-1,4-benzodiazepin-2-one (reacID# r1760)
N,N-Diethyl-m-toluamide -----> m-Toluamide (reacID# r1837)
2-Hydroxy-2',6'-diethyl-N-acetanilide -----> Formaldehyde + N-(2,6-Diethylphenyl)-2-hydroxyacetamide (reacID# r1694)
Hydroxymonodemethylisoproturon -----> Formaldehyde + 4'-(2-Hydroxyisopropyl)phenylurea (reacID# r0894)
N-Isopropylacetanilide -----> Acetanilide + Acetone (reacID# r0914)
Isoproturon -----> Formaldehyde + Monodemethylisoproturon (reacID# r0892)
1-Methylxanthine -----> Xanthine (reacID# r1331)
3-Methylxanthine -----> Xanthine (reacID# r1329)
Monodemethylisoproturon -----> Formaldehyde + Didemethylisoproturon (reacID# r0897)
Paraxanthine -----> 7-Methylxanthine (reacID# r1257)
Theobromine -----> 7-Methylxanthine (reacID# r1248)
Theophylline -----> 1-Methylxanthine (reacID# r1327)
Theophylline -----> 3-Methylxanthine (reacID# r1325)
Comments:
Oxidative removal of an aliphatic R group from a secondary or tertiary urea or amide nitrogen. An aldehyde is produced if the leaving R group is attached through a primary carbon. A ketone is produced if the leaving R group is attached through a secondary carbon. Oxidative cleavage of the C-N bond in amides and ureas are covered by a single rule, since there is no chemical reason to divide them. Cleavage of urea derivatives occurs between the N and the C with the most positive partial charge. Rule will produce cis products in rings with double bonds.
Similarities:
bt0067: secondary Amide --> Carboxylate + primary Amine
bt0068: N-substituted Urea derivative --> Carbamate + primary Amine
bt0430: tertiary Amide --> Carboxylate + secondary Amine
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Page Author(s):
Bo Kyeng Hou, Rachael Long, Michael Turnbull and Jiun-guo Yu
March 15, 2011
This is the EAWAG-BBD biotransformation rule, ruleID# bt0243.
It was generated on April 24, 2024 7:51:41 AM CDT.
© 2024, EAWAG.
