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

Bergh, Anders; Magnusson, Bengt-Göran; Ohlsson, Jörgen LU ; Wellmar, Ulf and Nilsson, Ulf LU (2001) In Glycoconjugate Journal 18(8). p.615-621
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
squaric decyl ester glycosides, neoglycoconjugates, didecyl squarate, C18 solid phase extraction
in
Glycoconjugate Journal
volume
18
issue
8
pages
615 - 621
publisher
Springer
external identifiers
  • scopus:0036702993
ISSN
1573-4986
DOI
10.1023/A:1020639603070
language
English
LU publication?
yes
id
d2185991-693f-430b-8bcd-29b91c23d3c4 (old id 1698032)
date added to LUP
2010-10-21 07:25:37
date last changed
2018-05-29 09:38:17
@article{d2185991-693f-430b-8bcd-29b91c23d3c4,
  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.},
  author       = {Bergh, Anders and Magnusson, Bengt-Göran and Ohlsson, Jörgen and Wellmar, Ulf and Nilsson, Ulf},
  issn         = {1573-4986},
  keyword      = {squaric decyl ester glycosides,neoglycoconjugates,didecyl squarate,C18 solid phase extraction},
  language     = {eng},
  number       = {8},
  pages        = {615--621},
  publisher    = {Springer},
  series       = {Glycoconjugate Journal},
  title        = {Didecyl squarate — A practical amino-reactive cross-linking reagent for neoglycoconjugate synthesis},
  url          = {http://dx.doi.org/10.1023/A:1020639603070},
  volume       = {18},
  year         = {2001},
}