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
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