Stereoselective Olefin Cyclopropanation under Aerobic Conditions with an Artificial Enzyme Incorporating an Iron-Chlorin e6 Cofactor
نویسندگان
چکیده
منابع مشابه
Stereoselective olefin cyclopropanation under aerobic conditions with an artificial enzyme incorporating an iron-chlorin e6 cofactor.
Myoglobin has recently emerged as a promising biocatalyst for catalyzing carbene-mediated cyclopropanation, a synthetically valuable transformation not found in nature. Having naturally evolved for binding dioxygen, the carbene transferase activity of this metalloprotein is severely inhibited by it, imposing the need for strictly anaerobic conditions to conduct these reactions. In this report, ...
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A triphenylphosphinegold(I)-catalyzed cyclopropanation of olefins using propargyl esters as gold(I)-carbene precursors is reported. This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective (up to 94% ee) preparation of vinyl cyclopropanes with high cis-selectivity.
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Artificial metalloenzymes (ArMs) formed by incorporating synthetic metal catalysts into protein scaffolds have the potential to impart to chemical reactions selectivity that would be difficult to achieve using metal catalysts alone. In this work, we covalently link an alkyne-substituted dirhodium catalyst to a prolyl oligopeptidase containing a genetically encoded L-4-azidophenylalanine residue...
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Organic chemists have always been fascinated by the cyclopropane subunit.1 The smallest cycloalkane is found as a basic structural element in a wide range of naturally occurring compounds.2 Moreover, many cyclopropane-containing unnatural products have been prepared to test the bonding features of this class of highly strained cycloalkanes3 and to study enzyme mechanism or inhibition.4 Cyclopro...
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The green heme protein sulfmyoglobin (SMb) has been suggested to contain a sulfur-modified iron chlorin prosthetic group. To evaluate this hypothesis, we have obtained high-frequency (71000 cm”) resonance Raman spectra of both oxidized and reduced SMb with 457.9-, 488.0-, 5 1 4 5 , 568.2-, and 647.1nm excitation. The SMb spectra are compared to those of native metand deoxymyoglobin (Mb). Vib...
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ژورنال
عنوان ژورنال: ACS Catalysis
سال: 2017
ISSN: 2155-5435,2155-5435
DOI: 10.1021/acscatal.7b02583