Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides.

Research output: Contribution to journalArticle

Abstract

Three series of sulfur-containing analogs to the selectively antiproliferative 2-(6-hydroxynaphthyl) β-d-xylopyranoside were synthesized and their biological properties investigated. A short, general route to hydroxynaphthyl disulfides from dihydroxynaphthalenes was developed to utilize the disulfide bond as a sulfur-selective protecting group to enable the orthogonal protection of hydroxyls and thiols. The results indicate that hydrophobic, uncharged oxygen–sulfur substituted naphthoxylosides are taken up by cells and initiate priming of GAG chains to a greater extent compared to the oxygen analogs. No correlation between priming ability and antiproliferative activity was observed.

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Authors
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Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Medicinal Chemistry

Keywords

  • Disulfides, Xylose, Glycosaminoglycan, Thio-β-d-xylopyranoside, Thioether
Original languageEnglish
Pages (from-to)5283-5299
JournalBioorganic & Medicinal Chemistry
Volume15
Issue number15
Publication statusPublished - 2007
Publication categoryResearch
Peer-reviewedYes

Bibliographic note

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)