GLYCOSYLATION OF PHENOLS - PREPARATION OF 1,2-CIS AND 1,2-TRANS GLYCOSYLATED TYROSINE DERIVATIVES TO BE USED IN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS

Authors
JENSEN KJ MELDAL M BOCK K
Citation
Kj. Jensen et al., GLYCOSYLATION OF PHENOLS - PREPARATION OF 1,2-CIS AND 1,2-TRANS GLYCOSYLATED TYROSINE DERIVATIVES TO BE USED IN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS, Journal of the Chemical Society. Perkin transactions. I, (17), 1993, pp. 2119-2129
Citations number
64
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
17
Year of publication
1993
Pages
2119 - 2129
Database
ISI
SICI code
0300-922X(1993):17<2119:GOP-PO>2.0.ZU;2-P
Abstract
The synthesis of four building blocks, N(alpha)-Fmoc-Tyr(Ac4-beta-D-Gl c)-OPfp 6, N(alpha)-Fmoc-Tyr(Bz4-alpha-D-Glc)-OPfp 16, c-Tyr[Ac4-alpha -D-Glc-(1-->4)-Ac3-beta-D-Glc]-OPfp 9 and -Tyr[Bz4-alpha-D-Glc-(1-->4) -Bz3-alpha-D-Glc]-OPfp 19, suitable for solid-phase glycopeptide synth esis is described. Several different glycosylation procedures were eva luated for this purpose. A remarkable solvent effect on the alpha:beta ratio was observed on going from dichloromethane to the nucleophilic solvent acetonitrile for the glycosylation reactions promoted by silve r triflate with participating protecting groups in the 2-position of t he glycosyl donor.