A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
Solid-phase synthesis of cyclic C-glycoside/amino acid hybrids by carbamate coupling chemistry and on-support cyclization
Tekijät: Katajisto J, Lonnberg H
Kustantaja: WILEY-V C H VERLAG GMBH
Julkaisuvuosi: 2005
Lehti:: European Journal of Organic Chemistry
Tietokannassa oleva lehden nimi: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Lehden akronyymi: EUR J ORG CHEM
Vuosikerta: 2005
Numero: 16
Aloitussivu: 3518
Lopetussivu: 3525
Sivujen määrä: 8
ISSN: 1434-193X
DOI: https://doi.org/10.1002/ejoc.200500273
Tiivistelmä
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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