Didecyl squarate — A practical amino-reactive cross-linking reagent for neoglycoconjugate synthesis
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/1698032
- author
- Bergh, Anders ; Magnusson, Bengt-Göran ; Ohlsson, Jörgen LU ; Wellmar, Ulf and Nilsson, Ulf LU
- organization
- publishing date
- 2001
- 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
- additional info
- 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)
- id
- d2185991-693f-430b-8bcd-29b91c23d3c4 (old id 1698032)
- date added to LUP
- 2016-04-01 15:41:18
- date last changed
- 2022-01-28 06:33:05
@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}}, keywords = {{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}}, doi = {{10.1023/A:1020639603070}}, volume = {{18}}, year = {{2001}}, }