A1 Refereed original research article in a scientific journal
Solid-phase synthesis of cyclic C-glycoside/amino acid hybrids by carbamate coupling chemistry and on-support cyclization
Authors: Katajisto J, Lonnberg H
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2005
Journal:: European Journal of Organic Chemistry
Journal name in source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Journal acronym: EUR J ORG CHEM
Volume: 2005
Issue: 16
First page : 3518
Last page: 3525
Number of pages: 8
ISSN: 1434-193X
DOI: https://doi.org/10.1002/ejoc.200500273
Abstract
A solid-supported synthesis of cyclic C-glycoside/amino acid conjugates is described. For this purpose, N-(tert-butoxycarbonyl)-[6-O-(p-nitrophenoxycarbonyl)-2,3,4-tri-O-(p-toluoyl)- beta-D-glycopyranosyl]methylamines derived from galactose and glucose were prepared and used as activated monomers together with appropriately protected amino acids. The solid phase assembly of the linear precursor was conducted by alternating peptide and carbamate coupling, using glutamate immobilized through its gamma-carboxy function to a SCAL linker as a handle. On-support cyclization followed by cleavage from the support gave the desired conjugates. Removal of the p-toluoyl protections was carried out in solution phase by methoxide ion-catalyzed transesterification in methanol.
A solid-supported synthesis of cyclic C-glycoside/amino acid conjugates is described. For this purpose, N-(tert-butoxycarbonyl)-[6-O-(p-nitrophenoxycarbonyl)-2,3,4-tri-O-(p-toluoyl)- beta-D-glycopyranosyl]methylamines derived from galactose and glucose were prepared and used as activated monomers together with appropriately protected amino acids. The solid phase assembly of the linear precursor was conducted by alternating peptide and carbamate coupling, using glutamate immobilized through its gamma-carboxy function to a SCAL linker as a handle. On-support cyclization followed by cleavage from the support gave the desired conjugates. Removal of the p-toluoyl protections was carried out in solution phase by methoxide ion-catalyzed transesterification in methanol.
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