Didecyl squarate — A practical amino-reactive cross-linking reagent for neoglycoconjugate synthesis

Anders Bergh, Bengt-Göran Magnusson, Jörgen Ohlsson, Ulf Wellmar, Ulf Nilsson

Research output: Contribution to journalArticlepeer-review

33 Citations (SciVal)

Abstract

The present paper describes the synthesis and use of the hydrophobic squaric decyl ester glycosides in neoglycoconjugate chemistry. The 2-aminoethyl glycosides of agr-D-mannopyranose, lactose, globotriose, globotetraose, GM3, and sialyl Lewisx, as well as the 2-(2-aminoethylthio)ethyl glycoside of agr-D-mannopyranose, beta-D-glucopyranose, and galabiose were reacted with squaric acid didecyl ester to afford the hydrophobic squaric decyl ester glycosides. These glycosides were efficient reagents for the conjugation to amino-functional microtiter plates, BSA and aminated Sepharose EAH 4B. The decyl ester moiety of the squaric decyl ester glycosides constitutes a traceless hydrophobic tag, which has the major advantage, as compared to the corresponding ethyl esters, that it enables easy purification of the glycosides with silica chromatography and that unreacted excesses glycosides from conjugation reaction mixtures can easily be recovered by means of C18 solid phase extraction.
Original languageEnglish
Pages (from-to)615-621
JournalGlycoconjugate Journal
Volume18
Issue number8
DOIs
Publication statusPublished - 2001

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

  • Organic Chemistry

Keywords

  • squaric decyl ester glycosides
  • neoglycoconjugates
  • didecyl squarate
  • C18 solid phase extraction

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