Naslov
Enzimski katalizirano otvaranje epoksida
(Enzyme catalysed ring-opening of epoxides)

Autori
Majerić-Elenkov, Maja ; Tang, Lixia ; Hauer, Bernhard ; Janssen, B. Dick

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

Izvornik
Knjiga sažetaka / Đ. Vasić Rački - Zagreb, 2007

ISBN
978-953-6894-29-1

Skup
XX. hrvatski skup kemičara i kemijskih inženjera

Mjesto i datum
Zagreb, Hrvatska, 26.02.2007. - 01.03.2007

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
kinetička rezolucija; epoksidi; cijanidi; azidi
(kinetic resolution; epoxides; cyanides; azides)

Sažetak
Halohydrin dehalogenase catalyses the ring-closure of halohydrins, as well as the ring-opening of epoxides with both halide and non-natural ionic nucleophiles, such as cyanide, azide and nitrite. What makes this enzyme attractive for synthetic purposes is the fact that ring opening reactions are irreversible and highly b-regioselective. Moreover, reactions can proceed with high enantioselectivity with a wide variety of synthetic substrates. In our screening among wild-type halohydrin dehalogenases, we have identified enzyme from Agrobacterium radiobacter as the most enantioselective in the cyanide-mediated ring opening reaction of epoxides. The enantioselectivity toward monosubstituted epoxides varies from moderate to high (E = 2-106), while resolution of 2, 2-disubstituted epoxides proceeds with excellent enantioselectivity (E ~ 200). This allows preparation of optically pure tertiary alcohols under mild conditions (room temperature and aqueous medium).

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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