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48 results on '"Nicotra, F"'

46. Synthesis of the Dimethyl Ester of 1-Deoxy-L-idonojirimycin-1-methylenephosphonate: A New Approach to Iminosugar Phosphonates

Author

Piergiuliano Bugada, Barbara La Ferla, Francesco Nicotra, LA FERLA, B, Bugada, P, and Nicotra, F

Subjects
chemistry.chemical_classification, Chemistry, Stereochemistry, iminosugar, Organic Chemistry, Iminosugar, General Medicine, Biochemistry, Aldehyde, Dimethyl ester, chemistry.chemical_compound, carbohydrate analog, inhibitors, CHIM/06 - CHIMICA ORGANICA, phosphonate, Stereoselectivity, Azide
Abstract

1-Methylenphosphonate-1-deoxy-L-idonojirimycin (1) has been synthesized starting from commercially available tetrabenzyl glucose, the key steps being substitution of the hydroxyl group at C-5 of compound 7 with an azido group, stereoselective reaction of the aldehyde at C-1 of compound 10 with dimethyl methylenephosphonate anion, conversion of the azide into an amino group, and finally cyclization of the aminoalcohol 12. [GRAPHICS]

Published
2006

47. Carbohydrate Scaffolds for the Production of Bioactive Compounds

Author

Francesco Nicotra, B. La Ferla, Francesco Peri, Laura Cipolla, C. Redaelli, Cipolla, L, Peri, F, LA FERLA, B, Redaelli, C, and Nicotra, F

Subjects
Bicyclic compound, Carbohydrate, Sugar amino acid, Chemistry, Libraries of compound, Organic Chemistry, General Medicine, Biochemistry, Combinatorial chemistry, Solid phase, CHIM/06 - CHIMICA ORGANICA, Organic chemistry, Food science
Abstract

Recent efforts in the use of carbohydrates as scaffolds for the production of bioactive compounds are reported. Orthogonally protected and solid phase supported monosaccharides for the production of libraries, exploiting the combinatorial approach by derivatisation of each hydroxyl group with different pharmacophores, are described. Example of peptidomimetics synthesised on a carbohydrate skeleton orienting proper amino acid residues, are also reported. In order to increase the conformational rigidity of the sugar templates, a variety of original bicyclic or policyclic polyfunctionalised structures have been synthesised from carbohydrates. Same of them have spiro or condensed bicyclic structures, others include one or more sugars in a macrocyclic framework or in cyclopeptides in order to induce bioactive peptide loops

Published
2006

48. Glycoconjugate and Oligosaccharide Mimetics by Chemoselective Ligation

Author

Barbara La Ferla, Francesco Peri, Francesco Nicotra, Laura Cipolla, Peri, F, Cipolla, L, LA FERLA, B, and Nicotra, F

Subjects
chemistry.chemical_classification, Anomer, Glycoconjugate, Stereochemistry, General Chemical Engineering, Chemoselective ligation, Carbohydrate mimetic, General Chemistry, Neoglycoconjugate, General Medicine, Oligosaccharide, Combinatorial chemistry, Epitope, Synthetic vaccines, chemistry, Nucleophile, In vivo, CHIM/06 - CHIMICA ORGANICA, Electrophile, Chemoselectivity
Abstract

Different approaches for the synthesis of neoglycoconjugates, exploiting chemoselective ligation procedures, are reported. Based on the reaction of the carbonyl group of ketones or aldehydes (including the anomeric centre of the sugar) with strong nucleophiles such as hydroxylamino- or hydrazino-derivatives, or on the addition of sulfidryl groups to a variety of electrophiles, these procedures afford bioactive neo-glycoconjugates avoiding protection–deprotection and activation steps. Conjugation of two copies of the C-saccharide analogue of the T n epitope with the immunogenic peptide OVA (327–339) by way of chemoselective ligation, afforded a neo-glycopeptide capable of inducing in vivo B- and T-cell response to tumours exposing T n epitope. To cite this article: F. Peri et al., C. R. Chimie 6 (2003).

Published
2004

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