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Synthesis and biology of bis-xylosylated dihydroxynaphthalenes.

Johnsson, Richard LU ; Mani, Katrin LU and Ellervik, Ulf LU (2007) In Bioorganic & Medicinal Chemistry 15(8). p.2868-2877
Abstract
The 10 analogous bis-xylosylated dihydroxynaphthalenes have been synthesized and their chemical and biological properties investigated. The yield of the xylosylation reactions can be correlated to the electrostatic potential, and thus to the nucleophilicity, for the oxygen atoms of the dihydroxynaphthalenes. The bis-xylosylated compounds were more stable compared to the mono-xylosylated ones. They initiate priming of glycosaminoglycan chains to less extent but the priming proceeds in two directions. Contrary to the mono-xylosylated analogs, the tested compounds did not show any antiproliferative properties.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Dihydroxynaphthalene, Glycosylation, Carbohydrates, Xylose
in
Bioorganic & Medicinal Chemistry
volume
15
issue
8
pages
2868 - 2877
publisher
Elsevier
external identifiers
  • wos:000245637200008
  • scopus:33947124596
ISSN
0968-0896
DOI
10.1016/j.bmc.2007.02.020
language
English
LU publication?
yes
id
05565fff-0e08-4ba7-af2d-9107b83860c6 (old id 165440)
alternative location
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=17321140&dopt=Abstract
date added to LUP
2007-07-16 10:00:33
date last changed
2017-01-01 04:55:02
@article{05565fff-0e08-4ba7-af2d-9107b83860c6,
  abstract     = {The 10 analogous bis-xylosylated dihydroxynaphthalenes have been synthesized and their chemical and biological properties investigated. The yield of the xylosylation reactions can be correlated to the electrostatic potential, and thus to the nucleophilicity, for the oxygen atoms of the dihydroxynaphthalenes. The bis-xylosylated compounds were more stable compared to the mono-xylosylated ones. They initiate priming of glycosaminoglycan chains to less extent but the priming proceeds in two directions. Contrary to the mono-xylosylated analogs, the tested compounds did not show any antiproliferative properties.},
  author       = {Johnsson, Richard and Mani, Katrin and Ellervik, Ulf},
  issn         = {0968-0896},
  keyword      = {Dihydroxynaphthalene,Glycosylation,Carbohydrates,Xylose},
  language     = {eng},
  number       = {8},
  pages        = {2868--2877},
  publisher    = {Elsevier},
  series       = {Bioorganic & Medicinal Chemistry},
  title        = {Synthesis and biology of bis-xylosylated dihydroxynaphthalenes.},
  url          = {http://dx.doi.org/10.1016/j.bmc.2007.02.020},
  volume       = {15},
  year         = {2007},
}