90633-88-8Relevant articles and documents
Synthesis of asymmetrically substituted scyllo-inositol
Rodriguez, Jacob,Walczak, Maciej A.
, p. 3281 - 3283 (2016)
scyllo-Inositol, a rare member of the inositol family, is present in axinelloside A, a marine metabolite with interesting inhibitory activity against human telomerase. Here, we present a concise synthesis of asymmetrically substituted scyllo-inositol star
Synthesis and mass spectrometric analysis of disaccharides from methanolysis of heparan sulfate
He, Qi Qi,Trim, Paul J.,Snel, Marten F.,Hopwood, John J.,Ferro, Vito
, p. 8791 - 8803 (2018/11/30)
The quantification of heparan sulfate (HS) in biological matrices, e.g., urine, cerebrospinal fluid, tissue samples etc., is of great importance for the diagnosis and prognosis of several of the mucopolysaccharidosis (MPS) disorders, which are lysosomal storage diseases of impaired glycosaminoglycan metabolism. The development of suitable assays for this purpose is challenging due to the high molecular weight and complexity of HS. Recent efforts towards this goal include the acid catalysed methanolysis of HS, which desulfates the polymer and results in the formation of disaccharide cleavage products which can be detected and quantified by LC-MS/MS. We have synthesized a library of 12 HS-derived disaccharides as methanolysis standards via the stereoselective 1,2-cis glycosylation of suitably protected GlcA and IdoA acceptors with a 2-deoxy-2-azido thioglucoside donor. This facilitated identification of the major peaks in the LC-MS/MS chromatograms, and potentially will allow the monitoring of specific metabolites as surrogate markers for genotype. This work also paves the way towards a fully quantitative LC-MS/MS assay for HS via the preparation of a suitably labelled derivative.
Synthesis of glyco-fused bicyclic compounds; Conformationally constrained scaffolds and useful polyfunctional building blocks
Cardona, Francisco,D'Orazio, Giuseppe,Silva, Artur M. S.,Nicotra, Francesco,La Ferla, Barbara
supporting information, p. 2549 - 2556 (2014/05/06)
We synthesized fused bicyclic polyfunctional compounds containing a highly hydroxylated pyran ring starting from commercially available methyl glucopyranoside and adopting a RCM annulation approach. The versatile α,β-unsaturated ketone group was introduced on the newly formed ring and, as an example of the potential of these polyfunctionalized building blocks, a tetracyclic compound was synthesized through a Diels-Alder cycloaddition reaction. Bicyclic polyfunctional glycol-fused compounds have been synthesized from commercially available methyl gluco-pyranoside. These molecules, with their high chirality content, presence of an α,β-unsaturated ketone and multiple hydroxyl groups represent useful building blocks for the preparation of complex, optically pure compounds. Copyright