Chemoenzymatic route to optically active dihydroxy cyclopenta [b]naphthalenones; precursors for decalin-based bioactive natural products

Basit Öğe Kaydı
dc.authorid0000-0002-8828-0507
dc.contributor.authorÖzdemirhan, Devrim
dc.contributor.authorSarıçelik, Özlem
dc.date.accessioned2021-06-23T19:49:00Z
dc.date.available2021-06-23T19:49:00Z
dc.date.issued2017
dc.departmentBAİBÜ, Fen Edebiyat Fakültesi, Kimya Bölümüen_US
dc.description.abstractThe development of an efficient chemoenzymatic route for the synthesis of optically active dihydroxy cyclopenta[b]naphthalenones; (+)-1,4a-dihydroxy-4a,5,6,7,8,8a,9,9a-octahydro-1H-cyclopenta[b]naphthalen-2(4H)-one (+)-10 and (+)-1,8a-dihydroxy-4a,5,6,7,8,8a,9,9a-octahydro-1H-cydopenta[b]naphthalen-2(4H)-one (+)-11 is described. Different lipases and esterases were tested in the enzymatic hydrolysis of the corresponding acetates (+/-)-4a-hydroxy-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-cyclopenta[b]naphthalen-1-yl acetate (+/-)-8, (+/-)-8a-hydroxy-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-cyclopenta[b]naphthalen-1-yl acetate (+/-)-9, CRL (Candida Rugosa Lipase) and PLE (Pig Liver Esterase) were found to be the most effectual enzymes; for (-)-8 by 47% ee with the corresponding dihydroxy; (+)-10 by 98% ee in the presence of CRL; whereas, ()-8 was obtained with 40% ee with the corresponding dihydroxy, (+)-10 with 58% ee in the PLE hydrolysis. It was concluded that CRL was the best biocatalyst for the substrate (+/-)-8. Moreover, enzymatic resolution in the presence of CRL yields, (-)-9 with 46% ee with the corresponding dihydroxy derivative; (+)-11 with 98% ee; however, in the presence of PLE, yields (-)-9 with 36% ee as well as the related dihydroxy derivative; (+)-11 with 49% ee respectively. The study concluded that CRL is the best biocatalyst for compounds (+/-)-8 and (+/-)-9. (C) 2016 Elsevier Ltd. All rights reserved.en_US
dc.identifier.doi10.1016/j.tetasy.2016.11.010
dc.identifier.endpage124en_US
dc.identifier.issn0957-4166
dc.identifier.issue1en_US
dc.identifier.scopus2-s2.0-85007039383en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.startpage118en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2016.11.010
dc.identifier.urihttps://hdl.handle.net/20.500.12491/9312
dc.identifier.volume28en_US
dc.identifier.wosWOS:000392771200014en_US
dc.identifier.wosqualityN/Aen_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.institutionauthorÖzdemirhan, Devrim
dc.institutionauthorSarıçelik, Özlem
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron-Asymmetryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectActive Dihydroxy Cyclopenta [b]Naphthalenonesen_US
dc.subjectChemoenzymatic Route
dc.subjectDecalin-Based Bioactive Natural Products
dc.titleChemoenzymatic route to optically active dihydroxy cyclopenta [b]naphthalenones; precursors for decalin-based bioactive natural productsen_US
dc.typeArticleen_US

Dosyalar

Orijinal paket
Listeleniyor 1 - 1 / 1
Küçük Resim Yok
İsim:
devrim-ozdemirhan.pdf
Boyut:
647.66 KB
Biçim:
Adobe Portable Document Format
Açıklama:
Tam Metin/Full Text
İndir

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Fen Bilimleri Enstitüsü/Diğer Yayınlar Koleksiyonu
Kimya Bölümü Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu