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Synthesis of Galβ1-3GlcNAc and Galβ1-3GlcNAcβ-SEt by an enzymatic method comprising the sequential use of β-galactosidases from bovine testes and Escherichia coli

Hedbys, Lars ; Johansson, Elisabet ; Mosbach, Klaus LU ; Larsson, Per-Olof LU ; Gunnarsson, Alf ; Svensson, Sigfrid and Lönn, Hans (1989) In Glycoconjugate Journal 6. p.161-168
Abstract
Galβ1-3GlcNAc (1) and Galβ1-3GlcNAcβ-SEt (2) were synthesized on a 100 mg scale by the transgalactosylation reaction of bovine testes β-galactosidase with lactose as donor andN-acetylglucosamine and GlcNAcβ-SEt as acceptors. In both cases the product mixtures contained unwanted isomers and were treated with β-galactosidase from Escherichia coli which has a different specificity, under conditions favouring hydrolysis, yielding besides the desired products, monosaccharides and traces of trisaccharides. The products were purified to >95% by gel filtration, with a final yield of 12% of 1 and 17% of 2, based on added acceptor. In a separate experiment Galβ1-6GlcNAcβ-SEt (3) was synthesized by the transglycosylation reaction using... (More)
Galβ1-3GlcNAc (1) and Galβ1-3GlcNAcβ-SEt (2) were synthesized on a 100 mg scale by the transgalactosylation reaction of bovine testes β-galactosidase with lactose as donor andN-acetylglucosamine and GlcNAcβ-SEt as acceptors. In both cases the product mixtures contained unwanted isomers and were treated with β-galactosidase from Escherichia coli which has a different specificity, under conditions favouring hydrolysis, yielding besides the desired products, monosaccharides and traces of trisaccharides. The products were purified to >95% by gel filtration, with a final yield of 12% of 1 and 17% of 2, based on added acceptor. In a separate experiment Galβ1-6GlcNAcβ-SEt (3) was synthesized by the transglycosylation reaction using β-galactosidase from Escherichia coli. No other isomers were detected. Compound 3 was purified by HPLC. (Less)
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organization
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Contribution to journal
publication status
published
subject
in
Glycoconjugate Journal
volume
6
pages
8 pages
publisher
Springer
ISSN
1573-4986
DOI
10.1007/BF01050645
language
English
LU publication?
yes
id
b21a0adb-ef14-4630-9eaa-bfe3f1e6a974
date added to LUP
2024-06-17 15:07:26
date last changed
2024-09-02 15:20:50
@article{b21a0adb-ef14-4630-9eaa-bfe3f1e6a974,
  abstract     = {{Galβ1-3GlcNAc (1) and Galβ1-3GlcNAcβ-SEt (2) were synthesized on a 100 mg scale by the transgalactosylation reaction of bovine testes β-galactosidase with lactose as donor andN-acetylglucosamine and GlcNAcβ-SEt as acceptors. In both cases the product mixtures contained unwanted isomers and were treated with β-galactosidase from Escherichia coli which has a different specificity, under conditions favouring hydrolysis, yielding besides the desired products, monosaccharides and traces of trisaccharides. The products were purified to >95% by gel filtration, with a final yield of 12% of 1 and 17% of 2, based on added acceptor. In a separate experiment Galβ1-6GlcNAcβ-SEt (3) was synthesized by the transglycosylation reaction using β-galactosidase from Escherichia coli. No other isomers were detected. Compound 3 was purified by HPLC.}},
  author       = {{Hedbys, Lars and Johansson, Elisabet and Mosbach, Klaus and Larsson, Per-Olof and Gunnarsson, Alf and Svensson, Sigfrid and Lönn, Hans}},
  issn         = {{1573-4986}},
  language     = {{eng}},
  pages        = {{161--168}},
  publisher    = {{Springer}},
  series       = {{Glycoconjugate Journal}},
  title        = {{Synthesis of Galβ1-3GlcNAc and Galβ1-3GlcNAcβ-SEt by an enzymatic method comprising the sequential use of β-galactosidases from bovine testes and <i>Escherichia coli</i>}},
  url          = {{http://dx.doi.org/10.1007/BF01050645}},
  doi          = {{10.1007/BF01050645}},
  volume       = {{6}},
  year         = {{1989}},
}