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Copper-free huisgen 1,3-dipolar cycloaddition to 3-benzotriazolo-3-deoxy-β-D-galactopyranoside : Cyclization of a galactopyranoside azide and benzyne

Öberg, Christopher T. LU ; Leffler, Hakon LU and Nilsson, Ulf J. LU (2010) In Trends in Carbohydrate Research 2(2). p.1-4
Abstract
Methyl 2-O-acetyl-3-benzotriazolo-4,6-O-benzylidene-3-deoxy- β -D-galactopyranoside was assembled by reacting benzyne, from 2-trimethylsilyl-trifluoromethansulfonylbenzene, and a secondary galactopyranoside azide in a copper-free Huisgen 1,3-dipolar cycloaddition. Following deprotection, the resulting benzotriazoles were evaluated as galectin inhibitors resulting in a 2-4 fold increase in affinity against galectin-1, -2 and -4 N-terminus compared to the parent methyl galactoside.
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author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Azide, Benzotriazole, Benzyne, Galactoside, Galectin, Huisgen
in
Trends in Carbohydrate Research
volume
2
issue
2
pages
4 pages
publisher
Association of Carbohydrate Chemists and Technologists
external identifiers
  • scopus:84861436010
ISSN
0975-0304
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: Division of Microbiology, Immunology and Glycobiology - MIG (013025200), Organic chemistry (S/LTH) (011001240)
id
19b7ab7a-ec2a-4b83-80c5-b9a6e53ceb8f (old id 1698123)
alternative location
http://www.trendscarbo.com/view_paper_all.php?id=829877055
date added to LUP
2016-04-04 09:45:45
date last changed
2025-10-14 10:08:04
@article{19b7ab7a-ec2a-4b83-80c5-b9a6e53ceb8f,
  abstract     = {{Methyl 2-O-acetyl-3-benzotriazolo-4,6-O-benzylidene-3-deoxy- β -D-galactopyranoside was assembled by reacting benzyne, from 2-trimethylsilyl-trifluoromethansulfonylbenzene, and a secondary galactopyranoside azide in a copper-free Huisgen 1,3-dipolar cycloaddition. Following deprotection, the resulting benzotriazoles were evaluated as galectin inhibitors resulting in a 2-4 fold increase in affinity against galectin-1, -2 and -4 N-terminus compared to the parent methyl galactoside.}},
  author       = {{Öberg, Christopher T. and Leffler, Hakon and Nilsson, Ulf J.}},
  issn         = {{0975-0304}},
  keywords     = {{Azide; Benzotriazole; Benzyne; Galactoside; Galectin; Huisgen}},
  language     = {{eng}},
  number       = {{2}},
  pages        = {{1--4}},
  publisher    = {{Association of Carbohydrate Chemists and Technologists}},
  series       = {{Trends in Carbohydrate Research}},
  title        = {{Copper-free huisgen 1,3-dipolar cycloaddition to 3-benzotriazolo-3-deoxy-β-D-galactopyranoside : Cyclization of a galactopyranoside azide and benzyne}},
  url          = {{http://www.trendscarbo.com/view_paper_all.php?id=829877055}},
  volume       = {{2}},
  year         = {{2010}},
}