Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles

Ling, Ke-Qing; Sayre, Lawrence M.

doi:10.1016/j.bmc.2005.02.013

Cited by 18 publications

(17 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the presence of either Mn(II) or Mn(III), the enzyme was not active with O 2 at atmospheric concentration or H 2 O 2 as sole oxidant in place of tert ‐butyl hydroperoxide (data not shown). The absence of activity with H 2 O 2 was surprising since many alkene cleavage reactions on highly similar substrates catalysed by peroxidases use this broadly accepted oxidant 6b,18. Interestingly, an artificial metallo‐peroxidase obtained via binding of cupric ions to a latent non‐metallated metal binding site in a 6‐phosphogluconolactonase showed significantly higher activity using tert ‐butyl hydroperoxide instead of H 2 O 2 19.…”

Section: Resultsmentioning

confidence: 99%

Oxidative Alkene Cleavage Catalysed by Manganese‐Dependent Cupin TM1459 from Thermotoga maritima

et al. 2015

View full text Add to dashboard Cite

An ovel biocatalytic oxidative alkene cleavagea ctivity was identifiedi np rotein TM1459 from Thermotoga maritima,aso far uncharacterised metalloprotein with ac upinf old, which preferentially binds manganese (over iron and zinc). Va rious styrene derivatives were converted with high chemoselectivity to the corresponding carbonylc ompounds by the manganese-containing protein,u sing organic hydroperoxide and molecular oxygen as oxidant. 4-Chloroacetophenone could be obtainedi n4 0% conversion from 4-chloro-a-methylstyrene (50 mM) in ab iphasic systemu sing ethyl acetate as organic cosolvent (5% v/v), while 76% conversion was obtained at al ower substrate concentration (10 mM). This novel biocatalyst can be easily over-expressed in Escherichia coli in exceptionally high yield andp urified, andt hus mayo ffer av aluablea nd safer alternative in oxidative C=Cb ond cleavage reactions for synthetic applications.

show abstract

Section: Resultsmentioning

confidence: 99%

Oxidative Alkene Cleavage Catalysed by Manganese‐Dependent Cupin TM1459 from Thermotoga maritima

et al. 2015

View full text Add to dashboard Cite

show abstract

“…A plausible reaction mechanism is proposed for condensation between indoles and anthranilic acids (Scheme , path A). With the assistance of anthranilic acid ( 1a ), similar to peroxidase-mediated oxidation of 3-alkylindoles, indole ( 1a ) was oxidized to indole-2, 3-epoxide ( 5 ). Intermolecular “N”-centered nucleophilic attack of the epoxide by 2a promoted by TMG to form ring-opening intermediate 6 .…”

mentioning

confidence: 99%

Synthesis of Tryptanthrins by Organocatalytic and Substrate Co-catalyzed Photochemical Condensation of Indoles and Anthranilic Acids with Visible Light and O₂

Huang

et al. 2016

Org. Lett.

View full text Add to dashboard Cite

A metal-free catalytic approach to tryptanthrins has been achieved for the first time. The unique process is realized by an organocatalytic and indole and anthranilic acid substrate co-catalyzed photochemical oxidative condensation with visible light and O. The truly environmentally friendly reaction conditions enable various reactants to participate in the process to deliver structurally diverse tryptanthrins.

show abstract

“…In the chloroperoxidase (CPO)‐catalysed oxidation of conjugated dienoic esters, alkene cleavage was observed as a side reaction (13%) with tert ‐butyl hydrogen peroxide under aerobic conditions (Scheme A) 51. Cleavage of 3‐methylindole and 3‐ethylindole was observed employing horseradish peroxidase (HRP) to yield the corresponding ring‐opened ortho ‐acyl formanilides and oxindoles on a 50‐mg scale with H 2 O 2 under aerobic conditions (Scheme B) 52. The radical oxidation was initiated by the addition of a catalytic amount of H 2 O 2 , whereby its concentration was maintained low (30 μM) to avoid enzyme deactivation.…”

Section: Alkene Cleavage By Enzymesmentioning

confidence: 99%

Oxidative Alkene Cleavage by Chemical and Enzymatic Methods

2013

View full text Add to dashboard Cite

The cleavage of alkenes to the corresponding carbonyl products is a widely employed method in organic synthesis, especially to introduce oxygen functionalities into molecules, remove protecting groups and tailor large molecules. Chemical methods available for alkene cleavage include, for instance, ozonolysis, several metal-based variants (KMnO 4 , OsO 4 , RuO 4 , etc.), electrochemical alternatives, singlet oxygen, hypervalent iodine and organic molecules in combination with oxygen. Furthermore, several enzymatic methods for alkene cleavage have been described to establish safe, mild and selective oxidation methods. Various heme and non-heme iron-dependent enzymes catalyse the alkene cleavage at ambient temperature and atmospheric pressure in an aqueous buffer, showing good chemo-and regioselectivities in selected cases. Quite recently some Cu-, Mn-and Ni-dependent enzymes have been identified for this reaction. This review gives an overview of the different chemical and enzymatic methods available for the cleavage of alkenes.

show abstract

Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles

Cited by 18 publications

References 41 publications

Oxidative Alkene Cleavage Catalysed by Manganese‐Dependent Cupin TM1459 from Thermotoga maritima

Oxidative Alkene Cleavage Catalysed by Manganese‐Dependent Cupin TM1459 from Thermotoga maritima

Synthesis of Tryptanthrins by Organocatalytic and Substrate Co-catalyzed Photochemical Condensation of Indoles and Anthranilic Acids with Visible Light and O₂

Oxidative Alkene Cleavage by Chemical and Enzymatic Methods

Contact Info

Product

Resources

About

Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles

Cited by 18 publications

References 41 publications

Oxidative Alkene Cleavage Catalysed by Manganese‐Dependent Cupin TM1459 from Thermotoga maritima

Oxidative Alkene Cleavage Catalysed by Manganese‐Dependent Cupin TM1459 from Thermotoga maritima

Synthesis of Tryptanthrins by Organocatalytic and Substrate Co-catalyzed Photochemical Condensation of Indoles and Anthranilic Acids with Visible Light and O2

Oxidative Alkene Cleavage by Chemical and Enzymatic Methods

Contact Info

Product

Resources

About

Synthesis of Tryptanthrins by Organocatalytic and Substrate Co-catalyzed Photochemical Condensation of Indoles and Anthranilic Acids with Visible Light and O₂