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Synthesis of aromatic C-xylosides by position inversion of glucose

Malmberg, Jesper LU ; Mani, Katrin LU orcid ; Säwén, Elin LU ; Wiren, Anders and Ellervik, Ulf LU orcid (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
2024-01-07 16:54:54
@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}},
  keywords     = {{structure-activity relationships; C-glycosides; carbohydrates; xylose}},
  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}},
}