141891-22-7Relevant academic research and scientific papers
Imino-oxy acetic acid dealkylation as evidence for an inner-sphere alcohol intermediate in the reaction catalyzed by peptidylglycine α-hydroxylating monooxygenase
McIntyre, Neil R.,Lowe Jr., Edward W.,Merkler, David J.
, p. 10308 - 10319 (2009)
Peptidylglycine α-hydroxylating monooxygenase (PHM, EC 1.14.17.3) catalyzes the stereospecific hydroxylation of a glycyl α-carbon in a reaction that requires O2 and ascorbate. Subsequent dealkylation of the α-hydroxyglycine by another enzyme, peptidylamidoglycolate lyase (PAL. EC 4.3.2.5), yields a bioactive amide and glyoxylate. PHM is a noncoupled, type II dicopper monooxygenase which activates O2 at only a single copper atom, CuM. In this study, the PHM mechanism was probed using a non-natural substrate, benzaldehyde imino-oxy acetic acid (BIAA). PHM catalyzes the O-oxidative dealkylation of BIAA to benzaldoxime and glyoxylate with no involvement of PAL. The minimal kinetic mechanism for BIAA was shown to be steady-state ordered using primary deuterium kinetic isotope effects. The D(V/K)APPARENT, BIAA decreased from 14.7 ± 1.0 as [O2] → 0 to 1.0 ± 0.2 as [O2] → ∞ suggesting the dissociation rate constant from the PHM·BIAA complex decreases as [O2] increases; thereby, reducing the steady-state concentration of [PHM]free. BIAA was further used to differentiate between potential oxidative Cu/O species using a QM/MM reaction coordinate simulation to determine which species could yield product O-dealkylation that matched our experimental data. The results of this study provided compelling evidence for the presence of a covalently linked CuII-alkoxide intermediate with a quartet spin state responsible BIAA oxidation.
The synthesis of novel oxime ethers and their effects on the senescence of cut carnation flowers
Zeng, Zhen,Jiang, Hong,Zhang, Haoyong,Jiang, Zhenhua
scheme or table, p. 463 - 470 (2012/05/20)
The high levels of ethylene in plants are involved in a range of harmful effects, such as the senescence of plants and the rotting of fruits. A series of novel oxime ethers were synthesized to counteract the ethylene effects. Their structures were characterized by IR, MS, and 1H NMR, and their effects on the senescence of cut carnation flowers were investigated. The results show that all of the target compounds extended the vase life of cut carnation, especially for compound 3i, which prolonged the vase life of cut carnation flowers to about 11 days, nearly 75% longer vase life compared to the control groups. Most of them were more effective than AgNO3 and aminooxyacetic acid. Springer Science+Business Media B.V. 2011.
(E)-(Arylmethyleneaminoxy)acetamides as analogues of neuroleptic benzamides: Synthesis and D2-dopaminergic binding affinity
Macchia,Manera,Martinelli,Orlandini,Romagnoli,Rossello,Chellini
, p. 719 - 724 (2007/10/03)
Some type B (E)-(arylmethyleneaminoxy)acetamides were synthesised as analogues of type A neuroleptic and antipsychotic benzamides, in which the aromatic group is substituted by a (methyleneaminoxy)methyl moiety (C = NOCH2, MAOMM). Theoretical studies were performed in order to verify whether conformational analogies could exist between type A and type B compounds. Type B compounds were tested for their D2-dopaminergic binding affinity which represents a valid indication of their potential neuroleptic and antipsychotic properties. Biological results indicate that the MAOMM is not able to substitute the aromatic group effectively in the field of neuroleptic benzamides. The results are discussed in the light of the structural analogies and the differences between the MAOMM and the aryl.
Synthesis and Biological Activity of Benzaldehyde O-Alkyloximes as Abscisic Acid Mimics (Part 1)
Yoshikawa, Hiromichi,Fujimoto, Eri,Doi, Keiko
, p. 256 - 260 (2007/10/02)
Twenty-four benzaldehyde O-alkyloximes having a carboxylic moiety at the α-position of the oxime-oxygen were prepared as abscisic acid (ABA) mimics.Their effects on some physiological and biochemical processes of selected plant species were investigated in comparison to those of ABA.The mimics exhibited ABA-like activity by inhibiting germination and α-amylase induction.They also induced stomatal closure coupled with a reduction in transpiration.
