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Influence of intramolecular hydrogen bonds on regioselectivity of glycosylation. Synthesis of lupane-type saponins bearing the OSW-1 saponin disaccharide unit and its isomers

SYSNO ASEP	0459173
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Influence of intramolecular hydrogen bonds on regioselectivity of glycosylation. Synthesis of lupane-type saponins bearing the OSW-1 saponin disaccharide unit and its isomers
Author(s)	Kuczynska, K. (PL) Cmoch, P. (PL) Rárová, L. (CZ) Oklešťková, Jana (UEB-Q)_{RID, ORCID, SAI} Korda, A. (PL) Pakulski, Z. (PL) Strnad, Miroslav (UEB-Q)_{RID, ORCID}
Source Title	Carbohydrate Research. - : Elsevier - ISSN 0008-6215 Roč. 423, MAR 24 (2016), s. 49-69
Number of pages	21 s.
Language	eng - English
Country	NL - Netherlands
Keywords	OSW-1 disaccharide ; Glycosylation ; Lupane saponins
Subject RIV	EB - Genetics ; Molecular Biology
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	000370809200003
DOI	10.1016/j.carres.2016.01.010
Annotation	A series of lupane-type saponins bearing OSW-1 disaccharide unit as well as its regio- and stereoisomers were prepared and used for the structure-activity relationships (SAR) study. Unexpected preference for 1 -> 4-linked regioisomers and an unusual inversion of the conformation of the sugar rings were noted. Cytotoxic activity of new lupane compounds was evaluated in vitro and revealed that some saponins exhibited an interesting bioactivity profile against human cancer cell lines. Influence of the protecting groups on the cytotoxicity was investigated. These results open the way to the synthesis of various lupane-type triterpene and saponin derivatives as potential anticancer compounds.
Workplace	Institute of Experimental Botany
Contact	David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469
Year of Publishing	2017

Number of the records: 1