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Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins
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SYSNO ASEP 0467449 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins Author(s) Sidoryk, K. (PL)
Rárová, L. (CZ)
Oklešťková, Jana (UEB-Q) RID, ORCID, SAI
Pakulski, Z. (PL)
Strnad, Miroslav (UEB-Q) RID, ORCID
Cmoch, P. (PL)
Luboradzki, R. (PL)Number of authors 7 Source Title Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520
Roč. 14, č. 43 (2016), s. 10238-10248Number of pages 11 s. Language eng - English Country GB - United Kingdom Keywords organoselenium compounds ; everninomicin 13,384-1 ; coupling-constants ; stereocontrolled synthesis ; glycosidase inhibitors ; cytotoxic agents ; in-vitro ; selenium ; derivatives ; thioglycosides Subject RIV CE - Biochemistry R&D Projects LO1204 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) GA14-19590S GA ČR - Czech Science Foundation (CSF) Institutional support UEB-Q - RVO:61389030 UT WOS 000387902900017 DOI 10.1039/c6ob01938b Annotation A practical synthesis of 28a-homo-28a-selenolupane triterpenes and the corresponding selenosaponins containing D-mannose, L-arabinose, L-rhamnose, and D-idose moieties is described. Selenium containing triterpenes were obtained from the readily available 3-O-allyl-homobetulin mesylate by nucleophilic substitution with the selenocyanate ion which upon reduction of theSeCN group afforded the free selenol. Glycosylation using classical Schmidt donors gave 1,2-trans selenosaponins as the main product as well as minute amounts of 1,2-cis isomers. This is one of the very few examples of the synthesis of selenoglycosides by direct glycosylation of free selenols. The studied selenol showed high resistance to air oxidation resulting in good stability during the synthesis of selenolupane derivatives. Cytotoxic activities of new homoselenolupane derivatives were also evaluated in vitro and revealed that some triterpenes exhibited an interesting profile against human cancer cell lines. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2017
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