SYNTHESIS OF GLYCOSYLTYROSINE BUILDING-BLOCKS FOR SOLID-PHASE GLYCOPEPTIDE ASSEMBLY - USE OF ARYL TERT-BUTYL ETHERS AS GLYCOSYL ACCEPTERS IN AROMATIC GLYCOSYLATIONS

Authors
VARGASBERENGUEL A MELDAL M PAULSEN H JENSEN KJ BOCK K
Citation
A. Vargasberenguel et al., SYNTHESIS OF GLYCOSYLTYROSINE BUILDING-BLOCKS FOR SOLID-PHASE GLYCOPEPTIDE ASSEMBLY - USE OF ARYL TERT-BUTYL ETHERS AS GLYCOSYL ACCEPTERS IN AROMATIC GLYCOSYLATIONS, Journal of the Chemical Society. Perkin transactions. I, (22), 1994, pp. 3287-3294
Citations number
43
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
22
Year of publication
1994
Pages
3287 - 3294
Database
ISI
SICI code
0300-922X(1994):22<3287:SOGBFS>2.0.ZU;2-9
Abstract
The synthesis of the suitably protected building blocks for solid-phas e glycopeptide synthesis. N-alpha-Fmoc-Tyr(Bz(4)-beta-D-Gal)-OPfp 3, N -alpha-Fmoc-Tyr(Bz(4)-alpha-D-Gal)-OPfp 4, N-alpha-Fmoc-Tyr(Bz(3)-alph a-L-Rha)-OPfp 6. N-alpha-Fmoc-Tyr[Bz(3)-alpha-L- Rha(1-->3)-Bz(3)-beta -D-Gal]-OPfp 18, and >4)-Bz(3)-alpha-DGlc(1-->4)-Bz(3)-beta-D-Glc]-OPf p 20, are described. The synthesis involves the coupling of the corres ponding glycosyl bromides with the aryl tert-butyl ether N-alpha-Fmoc- Tyr(Bu(t))O Pfp 1, using silver trifluoromethanesulfonate as promoter.