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[ CAS No. 769-78-8 ] {[proInfo.proName]}

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Chemical Structure| 769-78-8
Chemical Structure| 769-78-8
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Siriboe, Mary G ; Vargas, David A ; Fasan, Rudi DOI: PubMed ID:

Abstract: Chiral cyclopropanols are highly desirable building blocks for medicinal chemistry, but the stereoselective synthesis of these molecules remains challenging. Here, a novel strategy is reported for the diastereo- and enantioselective synthesis of cyclopropanol derivatives via the biocatalytic asymmetric cyclopropanation of vinyl esters with ethyl diazoacetate (EDA). A dehaloperoxidase enzyme from Amphitrite ornata was repurposed to catalyze this challenging cyclopropanation reaction, and its activity and stereoselectivity were optimized via protein engineering. Using this system, a broad range of electron-deficient vinyl esters were efficiently converted to the desired cyclopropanation products with up to 99.5:0.5 diastereomeric and enantiomeric ratios. In addition, the engineered dehaloperoxidase-based biocatalyst is able to catalyze a variety of other abiological carbene transfer reactions, including N?H/S?H carbene insertion with EDA as well as cyclopropanation with diazoacetonitrile, thus adding to the multifunctionality of this enzyme and defining it as a valuable new scaffold for the development of novel carbene transferases.

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Product Details of [ 769-78-8 ]

CAS No. :769-78-8 MDL No. :MFCD00048141
Formula : C9H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KOZCZZVUFDCZGG-UHFFFAOYSA-N
M.W : 148.16 Pubchem ID :13037
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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