Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/388322
- author
- Ågren, Jenny LU ; Billing, Johan LU ; Grundberg, Hans LU and Nilsson, Ulf LU
- organization
- publishing date
- 2006
- 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
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- 8db77836-5f60-470c-8ebd-4f7d8956f642 (old id 388322)
- date added to LUP
- 2016-04-01 16:49:51
- date last changed
- 2022-02-13 00:55:04
@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}}, keywords = {{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}}, doi = {{10.1055/s-2006-942503}}, year = {{2006}}, }