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

Författare

Summary, in English

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.

Publiceringsår

2007

Språk

Engelska

Sidor

5283-5299

Publikation/Tidskrift/Serie

Bioorganic & Medicinal Chemistry

Volym

15

Issue

15

Dokumenttyp

Artikel i tidskrift

Förlag

Elsevier

Ämne

  • Medicinal Chemistry

Nyckelord

  • Disulfides
  • Xylose
  • Glycosaminoglycan
  • Thio-β-d-xylopyranoside
  • Thioether

Status

Published

Forskningsgrupp

  • Glycobiology

ISBN/ISSN/Övrigt

  • ISSN: 0968-0896