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"Clickable" affinity ligands for effective separation of glycoproteins.

Suksrichavalit, Thummaruk LU ; Yoshimatsu, Keiichi LU ; Prachayasittikul, Virapong; Bülow, Leif LU and Ye, Lei LU (2010) In Journal of chromatography. A 1217. p.3635-3641
Abstract
In this paper, we present a new modular approach to immobilize boronic acid ligands that can offer effective separation of glycoproteins. A new "clickable" boronic acid ligand was synthesized by introducing a terminal acetylene group into commercially available 3-aminophenyl boronic acid. The clickable ligand, 3-(prop-2-ynyloxycarbonylamino)phenylboronic acid (2) could be easily coupled to azide-functionalized hydrophilic Sepharose using Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction under mild condition. Compared to other boronic acid affinity gels, the new affinity gel displayed superior effectiveness in separating model glycoproteins (ovalbumin and RNase B) from closely related bovine serum albumin and RNase A in the presence of... (More)
In this paper, we present a new modular approach to immobilize boronic acid ligands that can offer effective separation of glycoproteins. A new "clickable" boronic acid ligand was synthesized by introducing a terminal acetylene group into commercially available 3-aminophenyl boronic acid. The clickable ligand, 3-(prop-2-ynyloxycarbonylamino)phenylboronic acid (2) could be easily coupled to azide-functionalized hydrophilic Sepharose using Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction under mild condition. Compared to other boronic acid affinity gels, the new affinity gel displayed superior effectiveness in separating model glycoproteins (ovalbumin and RNase B) from closely related bovine serum albumin and RNase A in the presence of crude Escherichia coli proteins. Because of the simplicity of the immobilization through "click chemistry", the new ligand 2 is expected to not only offer improved glycoprotein separation in other formats, but also act as a useful building block to develop new chemical sensors for analysis of other glycan compounds. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of chromatography. A
volume
1217
pages
3635 - 3641
publisher
Elsevier
external identifiers
  • wos:000278158600001
  • pmid:20403604
  • scopus:77952668993
ISSN
1873-3778
DOI
10.1016/j.chroma.2010.03.050
language
English
LU publication?
yes
id
18e91592-f00e-402a-b61f-045260ecc9e0 (old id 1595081)
date added to LUP
2010-05-06 14:27:16
date last changed
2018-06-17 04:05:00
@article{18e91592-f00e-402a-b61f-045260ecc9e0,
  abstract     = {In this paper, we present a new modular approach to immobilize boronic acid ligands that can offer effective separation of glycoproteins. A new "clickable" boronic acid ligand was synthesized by introducing a terminal acetylene group into commercially available 3-aminophenyl boronic acid. The clickable ligand, 3-(prop-2-ynyloxycarbonylamino)phenylboronic acid (2) could be easily coupled to azide-functionalized hydrophilic Sepharose using Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction under mild condition. Compared to other boronic acid affinity gels, the new affinity gel displayed superior effectiveness in separating model glycoproteins (ovalbumin and RNase B) from closely related bovine serum albumin and RNase A in the presence of crude Escherichia coli proteins. Because of the simplicity of the immobilization through "click chemistry", the new ligand 2 is expected to not only offer improved glycoprotein separation in other formats, but also act as a useful building block to develop new chemical sensors for analysis of other glycan compounds.},
  author       = {Suksrichavalit, Thummaruk and Yoshimatsu, Keiichi and Prachayasittikul, Virapong and Bülow, Leif and Ye, Lei},
  issn         = {1873-3778},
  language     = {eng},
  pages        = {3635--3641},
  publisher    = {Elsevier},
  series       = {Journal of chromatography. A},
  title        = {"Clickable" affinity ligands for effective separation of glycoproteins.},
  url          = {http://dx.doi.org/10.1016/j.chroma.2010.03.050},
  volume       = {1217},
  year         = {2010},
}