Parallel solution synthesis of a 'carbohybrid' library designed to inhibit galactose-binding proteins
(1999) In Combinatorial Chemistry and High Throughput Screening 2(6). p.335-352- Abstract
Parallel solution S-alkylations of a 1-thio-β-D-galactopyranoside derivative with Michael acceptors and α-chloroketones, followed by ketone reductions, reductive aminations, and acylations were developed to yield a library of 1-thio-β-D-galactopyranosides carrying small and diverse polar- neutral, hydrophobic, aromatic, cationic, or anionic non-carbohydrate aglycon structures. Screening of the library against a panel of galactose recognizing plant lectins revealed μM inhibitors of toxin A of A. precatorius superior to the reference ligands lactose and N-acetyl lactosamine. Such small, monosaccharide based inhibitors are attractive lead-molecules for therapeutic development, since they are low-molecular, hydrolytically stable and more... (More)
Parallel solution S-alkylations of a 1-thio-β-D-galactopyranoside derivative with Michael acceptors and α-chloroketones, followed by ketone reductions, reductive aminations, and acylations were developed to yield a library of 1-thio-β-D-galactopyranosides carrying small and diverse polar- neutral, hydrophobic, aromatic, cationic, or anionic non-carbohydrate aglycon structures. Screening of the library against a panel of galactose recognizing plant lectins revealed μM inhibitors of toxin A of A. precatorius superior to the reference ligands lactose and N-acetyl lactosamine. Such small, monosaccharide based inhibitors are attractive lead-molecules for therapeutic development, since they are low-molecular, hydrolytically stable and more hydrophobic than natural oligosaccharides.
(Less)
- author
- Nilsson, U. J. LU ; Fournier, E. J.-L. ; Fryz, E. J. and Hindsgaul, O.
- publishing date
- 1999-12
- type
- Contribution to journal
- publication status
- published
- in
- Combinatorial Chemistry and High Throughput Screening
- volume
- 2
- issue
- 6
- pages
- 18 pages
- publisher
- Bentham Science Publishers
- external identifiers
-
- pmid:10644859
- scopus:0033394141
- ISSN
- 1386-2073
- language
- English
- LU publication?
- no
- id
- 1b6fe224-78d4-4bf5-b59a-09e22307e681
- date added to LUP
- 2023-02-07 08:57:55
- date last changed
- 2024-01-03 22:03:37
@article{1b6fe224-78d4-4bf5-b59a-09e22307e681,
abstract = {{<p>Parallel solution S-alkylations of a 1-thio-β-D-galactopyranoside derivative with Michael acceptors and α-chloroketones, followed by ketone reductions, reductive aminations, and acylations were developed to yield a library of 1-thio-β-D-galactopyranosides carrying small and diverse polar- neutral, hydrophobic, aromatic, cationic, or anionic non-carbohydrate aglycon structures. Screening of the library against a panel of galactose recognizing plant lectins revealed μM inhibitors of toxin A of A. precatorius superior to the reference ligands lactose and N-acetyl lactosamine. Such small, monosaccharide based inhibitors are attractive lead-molecules for therapeutic development, since they are low-molecular, hydrolytically stable and more hydrophobic than natural oligosaccharides.</p>}},
author = {{Nilsson, U. J. and Fournier, E. J.-L. and Fryz, E. J. and Hindsgaul, O.}},
issn = {{1386-2073}},
language = {{eng}},
number = {{6}},
pages = {{335--352}},
publisher = {{Bentham Science Publishers}},
series = {{Combinatorial Chemistry and High Throughput Screening}},
title = {{Parallel solution synthesis of a 'carbohybrid' library designed to inhibit galactose-binding proteins}},
volume = {{2}},
year = {{1999}},
}