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Peptide-like compounds containing an arginine have been shown to bind and stabilize the central helix of the Alzheimer's disease related amyloid-β peptide (Aβ) in an α-helical conformation, thereby delaying its aggregation into cytotoxic species. Here we study a novel Aβ targeting ligand AEDabDab containing the triamino acid,(More)
Novel, efficient and selective biocatalytic acylation / deacylation strategies have been used for the greener synthesis of precursors of different bicyclonucleosides. Biocatalytic methodology has also been developed for the separation of pyrano- and furanonucleosides, which is otherwise almost impossible to achieve by usual chemical approach.
An efficient and facile strategy has been developed for bromination of nucleosides using sodium monobromoisocyanurate (SMBI). Our methodology demonstrates bromination at the C-5 position of pyrimidine nucleosides and the C-8 position of purine nucleosides. Unprotected and also several protected nucleosides were brominated in moderate to high yields(More)
Use of benzoyl cyanide (BzCN) for benzoylation of nucleosides has been studied, both in pyridine and in ionic liquid BzCN in 1-methoxyethyl-3-methylimidazolium methanesulfonate as ionic liquid has been found to be a "green "alternative compared to the pyridine-BzCN system. An efficient and selective benzoylation of nucleosides of both, the 2'-deoxy- and the(More)
To obtain different amino acids with varying lipophilicity and that can carry up to three positive charges we have developed a number of new triamino acid building blocks. One set of building blocks was achieved by aminoethyl extension, via reductive amination, of the side chain of ortnithine, diaminopropanoic and diaminobutanoic acid. A second set of(More)
Candida antarctica lipase-B (CAL-B) immobilized on lewatite selectively acylated the primary hydroxyl group of the furanosyl nucleoside in a mixture of 1-(alpha-D-arabinofuranosyl)thymine and 1-(alpha-D-arabinopyranosyl)thymine. This selective biocatalytic acylation of furanosyl nucleoside has enabled us an easy separation of arabinofuranosyl thymine from(More)
Our aim was to study the impact of two proline chimeras, containing a glutamic acid side chain in cis- or trans-configuration, on secondary structure formation. We further investigated to what extent the configuration of the side chain contributes to the overall peptide conformation. We used a 10 residue peptide (IYSNPDGTWT) that forms a β-hairpin in water.(More)
The synthesis of novel C-4'-spiro-oxetano-α-L-ribonucleosides T and U in 39 and 45% overall yields have been achieved from 2',3',5'-tri-O-acetyl-4'-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosylthymine and 2',3',5'-tri-O-acetyl-4'-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosyluracil, respectively. Both the tosylated nucleoside precursors have been(More)
Synthesis of alpha-L-arabino- and alpha-D-arabino-configured pentofuranosyl nucleosides of four of the natural bases [thymine (ara-T), adenine (ara-A), cytosine (ara-C) and guanine (ara-G)] is reported together with hybridization properties of oligonucleotides containing alpha-L-ara-T and -A, alpha-D-ara-T and -A, and 2'-amino-alpha-L-ara-T monomers.(More)