| Yazarlar |
Nurhan. Horasan Kishali
|
|
Şengül Dilem Doğan
Erciyes Üniversitesi, Türkiye |
|
Ertan Şahin
Atatürk Üniversitesi, Türkiye |
Prof. Dr. Aslıhan GÜNEL
Ahi Evran Üniversitesi, Türkiye |
|
Yunus Kara
Atatürk Üniversitesi, Türkiye |
|
Metin Balcı
İstanbul Aydın Üniversitesi, Türkiye |
| Özet |
| Two new deoxycarbaheptopyranoses, 5a-carba-6-deoxy-α-dl-galacto- heptopyranose and 5a-carba-6-deoxy-α-dl-gulo-heptopyranose were prepared starting from cyclohexa-1,4-diene. The addition of dichloroketene to cyclohexa-1,4-diene followed by the subsequent reductive elimination and Baeyer-Villiger oxidation in turn led to the formation of a bicyclic lactone. Reduction of the lactone moiety followed by acetylation gave a diacetate with cis-configuration. The introduction of additional acetate functionality into the molecule was achieved by singlet oxygen ene-reaction. The formed hydroperoxide was reduced and then acetylated. The triacetate was further functionalized either by direct cis-hydroxylation using OsO4 or by epoxidation followed by a ring-opening reaction to give the title heptopyranose derivatives. One of the synthesized molecules, galacto-heptopyranose exhibited enzyme specific inhibition against α-glycosidase. On the other hand, they did not show any inhibition for α-amylase. However, both compounds, gulo-heptopyranose and galacto-heptopyranose increased the activity of α-amylase. © 2010 Elsevier Ltd. All rights reserved. |
| Anahtar Kelimeler |
| Carbapyranose | Carbasugar | Cyclitol | Deoxycarbasugar | Heptopyranose | Inositol |
| Makale Türü | Özgün Makale |
| Makale Alt Türü | SSCI, AHCI, SCI, SCI-Exp dergilerinde yayımlanan tam makale |
| Dergi Adı | TETRAHEDRON |
| Dergi ISSN | 0040-4020 |
| Dergi Tarandığı Indeksler | SCI-Expanded |
| Makale Dili | İngilizce |
| Basım Tarihi | 01-2011 |
