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Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition

Ågren, Jenny LU ; Billing, Johan LU ; Grundberg, Hans LU and Nilsson, Ulf LU (2006) In Synthesis p.3141-3145
Abstract
An efficient and modular synthesis of a chiral, amphiphilic, and fluorescent macrocycle is described. A bis-acetylene was prepared by coupling the amino group of a sugar delta-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar delta-amino acid carboxy group with a glutamic acid propiolyl amide. The bis-acetylene was reacted with 9,10-bis(azidomethyl)anthracene under Cu(I) catalysis to afford the target fluorescent macrocycle.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
carbohydrates, macrocycles, cycloadditions, azides, amino acids
in
Synthesis
issue
18
pages
3141 - 3145
publisher
Oxford Polytechnic, Oxford
external identifiers
  • wos:000241108700026
  • scopus:33749532306
ISSN
0039-7881
DOI
10.1055/s-2006-942503
language
English
LU publication?
yes
id
8db77836-5f60-470c-8ebd-4f7d8956f642 (old id 388322)
date added to LUP
2007-08-08 15:18:49
date last changed
2019-03-27 03:02:45
@article{8db77836-5f60-470c-8ebd-4f7d8956f642,
  abstract     = {An efficient and modular synthesis of a chiral, amphiphilic, and fluorescent macrocycle is described. A bis-acetylene was prepared by coupling the amino group of a sugar delta-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar delta-amino acid carboxy group with a glutamic acid propiolyl amide. The bis-acetylene was reacted with 9,10-bis(azidomethyl)anthracene under Cu(I) catalysis to afford the target fluorescent macrocycle.},
  author       = {Ågren, Jenny and Billing, Johan and Grundberg, Hans and Nilsson, Ulf},
  issn         = {0039-7881},
  keyword      = {carbohydrates,macrocycles,cycloadditions,azides,amino acids},
  language     = {eng},
  number       = {18},
  pages        = {3141--3145},
  publisher    = {Oxford Polytechnic, Oxford},
  series       = {Synthesis},
  title        = {Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition},
  url          = {http://dx.doi.org/10.1055/s-2006-942503},
  year         = {2006},
}