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Carbamate Linker Strategy in Solid‐Phase Synthesis of Amino‐Functionalized Glycoconjugates for Attachment to Solid Surfaces and Investigation of Protein‐Carbohydrate Interactions
Author(s) -
Spjut Sara,
Pudelko Maciej,
Hartmann Mirja,
Elofsson Mikael
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800670
Subject(s) - chemistry , glycoconjugate , solid phase synthesis , linker , trifluoroacetic acid , organic chemistry , combinatorial chemistry , amino acid , amine gas treating , polymer chemistry , stereochemistry , biochemistry , peptide , computer science , operating system
Amino‐functionalized serine‐based galactose and glucose neoglycolipids were prepared by solid‐phase synthesis using a carbamate strategy for anchoring amino functionalities to a (2‐fluoro‐4‐hydroxymethylphenoxy)acetic acid linker resin. Key synthetic steps were monitored with gel‐phase 19 F NMR spectroscopy. Cleavage from the solid support was performed with trifluoroacetic acid. The terminal amine of the neoglycolipids was conjugated with didecyl squarate and then immobilized in amino‐functionalized microtiter plates and the glycoconjugates were successfully probed with a galactose‐binding lectin.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)