Solvolytic depolymerization of chondroitin and dermatan sulfates

Toshihiko Toida, Kenji Sato, Noriko Sakamoto, Shinobu Sakai, Saori Hosoyama, Robert J. Linhardt

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

It is essential to establish a library of glycosaminoglycan oligosaccharides from the chondroitin and dermatan sulfates to investigate their biological functions and structure-activity relationships (SARs). There are several approaches to obtain oligosaccharides using chemical and enzymatic degradation procedures; however, purification of each resulting oligosaccharide is complicated because of the diversity of sulfonation patterns present in these oligosaccharides. We have developed a new method for the solvolytic degradation for chondroitin and dermatan sulfates to obtain an oligosaccharide mixture that can be easily purified into chondro/dermato oligosaccharides for characterization by both 1H NMR and MALDI-TOFMS. These oligosaccharides have a methyl-esterified uronate residue and a methyl 2-acetamido-2-deoxy-d-galactofuranoside at the nonreducing and reducing ends, respectively. All other internal repeating disaccharide units were desulfonated, but maintained their core carbohydrate structures.

Original languageEnglish
Pages (from-to)888-893
Number of pages6
JournalCarbohydrate Research
Volume344
Issue number7
DOIs
StatePublished - 12 May 2009
Externally publishedYes

Keywords

  • Chondroitin sulfate
  • Dermatan sulfate
  • Oligosaccharide depolymerization
  • Solvolysis
  • Sulfonation

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