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Pregled bibliografske jedinice broj: 1151685

Synthesis and kinetic resolution of propargylic epoxides


Kolman, Robert Junior; Mehić, Emina; Majerić Elenkov, Maja; Dokli, Irena
Synthesis and kinetic resolution of propargylic epoxides // BioTrans 2021 - Book of abstracts
Graz | Austria | Europe | Worldwide online, 2021. str. xx-xx (poster, međunarodna recenzija, sažetak, znanstveni)


CROSBI ID: 1151685 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Synthesis and kinetic resolution of propargylic epoxides

Autori
Kolman, Robert Junior ; Mehić, Emina ; Majerić Elenkov, Maja ; Dokli, Irena

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
BioTrans 2021 - Book of abstracts / - , 2021, Xx-xx

Skup
15th International Symposium on Biocatalysis and Biotransformations (Biotrans 2021)

Mjesto i datum
Graz | Austria | Europe | Worldwide online, 19-22.07.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
halohydrin dehalogenase ; propargylic epoxide ; biocatalysis ; kinetic resolution

Sažetak
Halohydrin dehalogenases (HHDHs) are versatile biocatalysts that facilitate the conversion between halohydrins and epoxides in both directions. Their ability to catalyze enantioselective epoxide ring-opening reactions with different nucleophiles (azide, cyanide, cyanate, thiocyanate etc.) can be used in synthesis of optically active epoxides, β- substituted alcohols and heterocyclic compounds. Further transformation (hydrolysis, reduction, intermolecular click reactions) gives rise to valuable building blocks (e. g. amino alcohols, aziridines, triazoles, oxazolidinones) in synthesis of pharmaceutical and natural compounds. [1] Propargylic epoxides and alcohols, owing to the presence of a triple bond, undergo various intermolecular and intramolecular reactions.[2, 3] Unfortunately, there are few described methods for enantioselective synthesis of these compounds, and those available require expensive or custom-made catalysts. Using propargylic epoxides as substrates of HHDHs, enantiomerically pure starting compounds for triple bond and/or nucleophile transformations, such as intramolecular click reactions, can be obtained. Therefore, the synthesis of substituted propargylic epoxides and subsequent enantioselective ring opening by halohydrin dehalogenases (HheA-N178A and HheC) was described (Figure 1). Phenyl-, tert-butyl- and cyclopentyl- substituted epoxides were synthesized from the corresponding terminal acetylenes by introduction and epoxidation of a double bond. Also, p- and m- tolyl derivatives were synthesized in a similar reaction sequence, starting from the corresponding iodotoluene and trimethylsilylacetylene. Kinetic resolution reactions in the presence of sodium azide were catalyzed by two HHDHs with opposite stereopreference. With both enzymes reactions yielded enantiomerically pure secondary azido alcohols (e.e. > 99%, E > 200). While HheA- N178A gave mostly (S)-β-azido alcohol (β : α ratio between 90:10 and 54:46), HheC yielded almost exclusively (R)-β-azido alcohol (up to to 99:1).

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove:
Institut "Ruđer Bošković", Zagreb


Citiraj ovu publikaciju:

Kolman, Robert Junior; Mehić, Emina; Majerić Elenkov, Maja; Dokli, Irena
Synthesis and kinetic resolution of propargylic epoxides // BioTrans 2021 - Book of abstracts
Graz | Austria | Europe | Worldwide online, 2021. str. xx-xx (poster, međunarodna recenzija, sažetak, znanstveni)
Kolman, R., Mehić, E., Majerić Elenkov, M. & Dokli, I. (2021) Synthesis and kinetic resolution of propargylic epoxides. U: BioTrans 2021 - Book of abstracts.
@article{article, year = {2021}, pages = {xx-xx}, keywords = {halohydrin dehalogenase, propargylic epoxide, biocatalysis, kinetic resolution}, title = {Synthesis and kinetic resolution of propargylic epoxides}, keyword = {halohydrin dehalogenase, propargylic epoxide, biocatalysis, kinetic resolution}, publisherplace = {Graz | Austria | Europe | Worldwide online} }
@article{article, year = {2021}, pages = {xx-xx}, keywords = {halohydrin dehalogenase, propargylic epoxide, biocatalysis, kinetic resolution}, title = {Synthesis and kinetic resolution of propargylic epoxides}, keyword = {halohydrin dehalogenase, propargylic epoxide, biocatalysis, kinetic resolution}, publisherplace = {Graz | Austria | Europe | Worldwide online} }




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