N(OMe)-linked disaccharide analogues, isosteric to the corresponding natural disaccharides, have been synthesized by chemoselective assembly of unprotected natural monosaccharides with methyl 6-deoxy-6-methoxyamino-alpha-D-glucopyranoside in an aqueous environment. The coupling reactions were found to be chemo- and stereoselective affording beta-(1-->6) disaccharide mimics when using Glc and GlcNAc; in the case of Gal, the beta-anomer was prevalent (beta:alpha=7:1). An iterative method for the synthesis of linear N(OMe) oligosaccharide analogues was demonstrated, based on the use of an unprotected monosaccharide building block in which an oxime functionality at C-6 is converted during the synthesis into the corresponding methoxyamino group. The conformational analysis of these compounds was carried out by using NMR spectroscopy, ab initio, molecular mechanics, and molecular dynamics methods. Optimized geometries and energies of fourteen conformers for each compound have been calculated at the B3LYP/6-31G* level. Predicted conformational equilibria were compared with the results based on NMR experiments and good agreement was found. It appears that N(OMe)-linked disaccharide analogues exhibit a slightly different conformational behavior to their parent natural disaccharides.

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The European eel (Anguilla anguilla) is a critically endangered species. The impact of environmental contamination on this species has been highlighted as contributing to the decline in recruitment. The Mar Menor hypersaline coastal lagoon (SE Spain) is one of the most productive fisheries of European eel in Europe, making it a critical habitat for species conservation. The present study aimed to provide an initial overview of the impact of organic chemical contaminants on the European eel and the potential sublethal effects of chemical pollution on pre-migrating eels in this hypersaline habitat. We investigated muscle bioaccumulation of main persistent and hazardous organic contaminants (including some current-use pesticides) and genotoxicity, neurotoxicity, and xenobiotic detoxification system responses. The findings show that lagoon eels were exposed to high levels of legacy organochlorine contaminants, recently banned pesticides (chlorpyrifos), and some emerging chemicals. Some individuals surpassed the maximum levels of CBs authorized by the European Commission for human consumption. In this species, residuals of chlorpyrifos, pendimethalin, and chlorthal dimethyl have been reported for the first time. This field study provides relevant data to stock management and human health consumption and provides the first biomarker responses in European eel under permanent hypersaline conditions. Furthermore, the high frequency of micronuclei in peripheral erythrocytes of lagoon eels indicates sublethal genotoxic effects on the organism. Overall, the European eels growing and maturing in the Mar Menor lagoon are exposed to toxic and carcinogenic chemicals. The lack of seafood safety regulations for human consumption for some legacy chemicals that were measured in high concentrations in our study requires special action. Further biomonitoring and research are recommended to protect the animal, public, and environmental health.