The synthesis, NMR structure determination, and molecular modelling of the conformationally restricted diastereomeric sugar azido acids 1 and 2 are presented. The bicyclic structures of these compounds are obtained through a iodocyclization reaction on the C-allyl glycoside of the D-arabinofuranose. Cyclic tetrapeptide 11 containing the amino acid derived from 1 linked to the RGD sequence has been synthesized; this compound was found to be a selective antagonist of αvβ3 integrins expressed on GM 7373 cells

Peri, F., Bassetti, R., Caneva, E., DE GIOIA, L., LA FERLA, B., Presta, M., et al. (2002). Arabinose-derived Bicyclic Amino Acids: Synthesis, Conformational Analysis and Construction of an avb3-selective RGD Peptide. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1, 2002(5), 368-644 [10.1039/b110453e].

Arabinose-derived Bicyclic Amino Acids: Synthesis, Conformational Analysis and Construction of an avb3-selective RGD Peptide

PERI, FRANCESCO;DE GIOIA, LUCA;LA FERLA, BARBARA;NICOTRA, FRANCESCO
2002

Abstract

The synthesis, NMR structure determination, and molecular modelling of the conformationally restricted diastereomeric sugar azido acids 1 and 2 are presented. The bicyclic structures of these compounds are obtained through a iodocyclization reaction on the C-allyl glycoside of the D-arabinofuranose. Cyclic tetrapeptide 11 containing the amino acid derived from 1 linked to the RGD sequence has been synthesized; this compound was found to be a selective antagonist of αvβ3 integrins expressed on GM 7373 cells
Articolo in rivista - Articolo scientifico
glycomimetic, sugar aminoacid
English
2002
2002
5
368
644
none
Peri, F., Bassetti, R., Caneva, E., DE GIOIA, L., LA FERLA, B., Presta, M., et al. (2002). Arabinose-derived Bicyclic Amino Acids: Synthesis, Conformational Analysis and Construction of an avb3-selective RGD Peptide. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1, 2002(5), 368-644 [10.1039/b110453e].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/17041
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