Synthesis of bromo-conduritol-B and bromo-conduritol-C as glycosidase inhibitors

Date

2009-03-10

Author

Cantekin, Seda
Baran, Arif
Caliskan, Rasit
Balcı, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

187
views

0
downloads

For the synthesis of bromo-conduritol-B skeleton, bromo-1,4-benzoquinone was subjected to bromination followed by the reduction of the carbonyl groups with NaBH4. Substitution of bromides bonded to sp(3)-hybridized carbon atoms with AgOAc gave the bromo-concluritol-B tetraacetate in high yield. For the construction of bromo-conduritol-C skeleton, 2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole was used as the starting material. Photooxygenation of the diene unit gave an unsaturated bicyclic endoperoxide. Bromine was incorporated into the molecule by the addition of bromine to the double bond. Opening of the peroxide linkage followed by HBr elimination and reduction of the carbonyl group provided the conduritol-C structure in good yield. Bromo-conduritol-B exhibited strong enzyme-specific inhibition against alpha-glycosidase.

Subject Keywords

Quinones, Endoperoxides, Conduritol-B, Conduritol-C, Haloconduritol, Enzyme inhibition

URI

https://hdl.handle.net/11511/51685

Journal

CARBOHYDRATE RESEARCH

DOI

https://doi.org/10.1016/j.carres.2008.12.005

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis and electrochemical studies of fluorene and benzimidazole containing conjugated polymers Namal, İmge; Toppare, Levent Kamil; Arslan Udum, Yasemin; Department of Chemistry (2013) The synthesis and characterization of two donor acceptor type conjugated polymers were investigated. The electrochemical properties were examined using cyclic voltammetry, spectroelectrochemistry and kinetic studies. The increase in the alkyl chain length attached to the fluorene unit was investigated by the corresponding electrochemical characteristics. The synthesis was carried out via Stille coupling of 4,7- dibromo-4'-(tert-butyl)spiro[benzo[d]imidazole-2,1' cyclohexane] and 2,5- bis(tributylstannyl)thi...
Synthesis of Ferrocenyl Substituted Aziridines Zeytinci, Serhat; Doğan, Özdemir; Department of Chemistry (2006) Immobilization of tyrosinase enzyme was performed in the matrices obtained via copolymerization of terephthalic acid bis-(2-thiophen-3-yl ethyl) ester (TATE) with pyrrole. During electrochemical polymerization of pyrrole, enzyme molecules were entrapped in the copolymer matrice. Activity measurements were performed by using Besthorn̕s Hydrazone method which includes spectrophotometric analysis of quinones produced by the enzyme. Enzyme electrodes were characterized in terms of maximum reaction rate (Vmax) a...
Benzoylformate decarboxylase from Pseudomonas putida as stable catalyst for the synthesis of chiral 2-hydroxy ketones Iding, H; Dunnwald, T; Greiner, L; Liese, A; Muller, M; Siegert, P; Grotzinger, J; Demir, Ayhan Sıtkı; Pohl, M (2000-04-14) The thiamin diphosphate- and Mg2+-dependent enzyme benzoylformate decarboxylase (BFD) from Pseudomonas putida was characterized with respect to its suitability to catalyze the formation of chiral 2-hydroxy ketones in a benzoin-condensation type reaction. Carboligation constitutes a side reaction of BFD, whereas the predominant physiological task of the enzyme is the non-oxidative decarboxylation of benzoylformate. For this purpose the enzyme was obtained in sufficient purity from Pseudomonas putida cells in...
Synthesis and characterization of hyperbranched and air drying fatty acid based resins Bat, Erhan; Kisakurek, D; Akhmedov, IM (Elsevier BV, 2006-04-01) In this research four hyperbranched resins having fatty acid residues were synthesized. Dipentaerythritol, which was used as the core molecule of the resins, was twice esterified with dimethylol propionic acid. This resin was then esterified with the castor oil fatty acids. The hydroxyl group present in the ricinoleic acid which constitutes almost 87% of the castor oil fatty acids was then reacted with linseed oil fatty acids and benzoic acid. The linseed fatty acids were incorporated into the structure to ...
Synthesis of ferrocenyl quinolines Zora, Metin (Elsevier BV, 2008-06-01) A convenient one-pot synthesis of ferrocenyl-substituted quinolines via a molecular iodine-catalyzed reaction of ferrocenylimines with enolizable aldehydes is reported. First, nucleophilic addition of the in situ generated enol to ferrocenylimine produces beta-anilinopropionaldehyde, which then undergoes intramolecular Friedel-Crafts reaction to give dihydroquinoline derivative. Finally, subsequent dehydration and aerobic oxidation affords ferrocenyl quinolines.

Citation Formats

S. Cantekin, A. Baran, R. Caliskan, and M. Balcı, “Synthesis of bromo-conduritol-B and bromo-conduritol-C as glycosidase inhibitors,” CARBOHYDRATE RESEARCH, pp. 426–431, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51685.