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Synthesis of aromatic C-xylosides by position inversion of glucose

Malmberg, Jesper LU ; Mani, Katrin LU ; Säwén, Elin LU ; Wiren, Anders and Ellervik, Ulf LU (2006) In Bioorganic & Medicinal Chemistry 14(19). p.6659-6665
Abstract
Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.
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author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
structure-activity relationships, C-glycosides, carbohydrates, xylose
in
Bioorganic & Medicinal Chemistry
volume
14
issue
19
pages
6659 - 6665
publisher
Elsevier
external identifiers
  • wos:000240650500021
  • pmid:16782347
  • scopus:33747391997
ISSN
0968-0896
DOI
10.1016/j.bmc.2006.05.068
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
91c61442-20f5-4f49-9053-b8deb5778094 (old id 393271)
date added to LUP
2016-04-01 11:41:35
date last changed
2021-02-17 07:26:25
@article{91c61442-20f5-4f49-9053-b8deb5778094,
  abstract     = {Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.},
  author       = {Malmberg, Jesper and Mani, Katrin and Säwén, Elin and Wiren, Anders and Ellervik, Ulf},
  issn         = {0968-0896},
  language     = {eng},
  number       = {19},
  pages        = {6659--6665},
  publisher    = {Elsevier},
  series       = {Bioorganic & Medicinal Chemistry},
  title        = {Synthesis of aromatic C-xylosides by position inversion of glucose},
  url          = {http://dx.doi.org/10.1016/j.bmc.2006.05.068},
  doi          = {10.1016/j.bmc.2006.05.068},
  volume       = {14},
  year         = {2006},
}