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Synthesis of migrastatin analogues as inhibitors of tumour cell migration: exploring structural change in and on the macrocyclic ring
(Wiley, 2015-11-04)
Migrastatin and isomigrastatin analogues have been synthesised in order to contribute to structure-activity studies on tumour cell migration inhibitors. These include macrocycles varying in ring size, functionality and ...
Multivalent carbohydrate-lectin interactions: the way synthetic chemistry enables insights into nanometric recognition
(MDPI Open Access, 2016-05-13)
Glycan recognition by sugar receptors (lectins) is intimately involved in many aspects of cell physiology. However, the factors explaining the exquisite selectivity of their functional pairing are not yet fully understood. ...
Glycoclusters as lectin inhibitors: comparative analysis on two plant agglutinins with different folding as a step towards rules for selectivity
(Elsevier, 2015-09-23)
The emerging physiological significance of carbohydrate (glycan) protein (lectin) recognition engenders the interest to design synthetic inhibitors with a high level of selectivity among natural sugar receptors. Plant ...
SnCl4- and TiCl4-catalyzed anomerization of acylated O- and S-Glycosides: analysis of factors that lead to higher alpha:beta anomer ratios and reaction rates
(American Chemical Society, 2010-09-13)
The quantification of factors that influence both rates and stereoselectivity of anomerization reactions catalyzed by SnCl4 and TiCl4 and how this has informed the synthesis of alpha-O- and alpha-S-glycolipids is discussed ...
Lectins: getting familiar with translators of the sugar code
(MDPI, 2015-01-22)
The view on the significance of the presence of glycans in glycoconjugates is undergoing a paradigmatic change. Initially mostly considered to be rather inert and passive, the concept of the sugar code identifies glycans ...
Combining glycocluster synthesis with protein engineering: an approach to probe into the significance of linker length in a tandem-repeat-type lectin (galectin-4)
(Elsevier, 2014-05-07)
Complementarity in lectin-glycan interactions in situ is assumed to involve spatial features in both the lectin and the glycan, giving a functional meaning to structural aspects of the lectin beyond its carbohydrate-binding ...
Decorated macrocycles via ring-closing double-reductive amination. Identification of an apoptosis inducer of leukemic cells that at least partially antagonizes a 5-HT2 receptor
(American Chemical Society, 2015-03-16)
A build-couple-pair strategy, including double-reductive amination macrocyclization, has been used to generate decorated macrocycles (eannaphanes) with an embedded triazole and monosaccharide. Biological screening led to ...
Synthesis of iminosugar derivatives presenting naphthyl and alkyl amine interacting groups and binding to somatostatin receptors
(Royal Society of Chemistry, 2014-03-20)
The synthesis of 1-deoxynojirimycin (DNJ) derivatives presenting a 2-naphthylmethyl and an alkyl amino side chain from L-sorbose is described. The synthetic derivatives were tested for their ability to inhibit the binding ...
Synthesis of migrastatin and its macroketone analogue and in vivo FRAP analysis of the macroketone on E-Cadherin dynamics
(Wiley-VCH Verlag, 2014-06-11)
An efficient and scalable synthesis of a key acyclic intermediate used for the preparation of migrastatin and its macroketone analogue is described; Brown alkoxyallylation is the key step for this synthesis. The macroketone ...
Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon
(Elsevier, 2014-03-16)
The synthesis of 1,2,3-triazole containing analogues of a-GalCer and galacturonic acid containing Sphingomonous cell wall antigens is described. Anomerisation was used to provide the required cc-glycosyl azide precursor. ...