Regioselective reductive openings of acetals; Mechanistic details and synthesis of fluorescently labeled compounds
(2006) In Journal of Organic Chemistry 71(9). p.3444-3451- Abstract
- Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3 center dot NMe3 center dot AlCl3, was investigated, and a mechanism where the outcome is directed by the electrostatic potential of the two oxygen atoms is presented. The regioselective acetal opening was used in the synthesis of a fluorescently labeled analogue to antiproliferative xylosides. The fluorescently labeled xyloside was tested for uptake, anti proliferative activity, and glycosaminoglycan priming in different cell lines. The xyloside was taken up by all cell lines but did not initiate glycosaminoglycan biosynthesis.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/410698
- author
- Johnsson, Richard LU ; Mani, Katrin LU ; Cheng, Fang LU and Ellervik, Ulf LU
- organization
- publishing date
- 2006
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of Organic Chemistry
- volume
- 71
- issue
- 9
- pages
- 3444 - 3451
- publisher
- The American Chemical Society (ACS)
- external identifiers
-
- wos:000237027000015
- scopus:33646261669
- ISSN
- 1520-6904
- DOI
- 10.1021/jo0526284
- 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), Glycobiology (013212006)
- id
- 815c7b30-5f13-442c-84e3-0dc8df96a35a (old id 410698)
- date added to LUP
- 2016-04-01 11:35:28
- date last changed
- 2024-06-03 12:55:04
@article{815c7b30-5f13-442c-84e3-0dc8df96a35a, abstract = {{Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3 center dot NMe3 center dot AlCl3, was investigated, and a mechanism where the outcome is directed by the electrostatic potential of the two oxygen atoms is presented. The regioselective acetal opening was used in the synthesis of a fluorescently labeled analogue to antiproliferative xylosides. The fluorescently labeled xyloside was tested for uptake, anti proliferative activity, and glycosaminoglycan priming in different cell lines. The xyloside was taken up by all cell lines but did not initiate glycosaminoglycan biosynthesis.}}, author = {{Johnsson, Richard and Mani, Katrin and Cheng, Fang and Ellervik, Ulf}}, issn = {{1520-6904}}, language = {{eng}}, number = {{9}}, pages = {{3444--3451}}, publisher = {{The American Chemical Society (ACS)}}, series = {{Journal of Organic Chemistry}}, title = {{Regioselective reductive openings of acetals; Mechanistic details and synthesis of fluorescently labeled compounds}}, url = {{http://dx.doi.org/10.1021/jo0526284}}, doi = {{10.1021/jo0526284}}, volume = {{71}}, year = {{2006}}, }