Analysis of sulfate esters by solvolysis or hydrolysis

Area of Science:

• Biochemistry
• Carbohydrate Chemistry

Background:

• Sulfate esters are common modifications on N- and O-linked glycans and glycosaminoglycans (GAGs).
• Enzymatic removal of sulfate esters is limited by the availability of specific sulfatases.
• Chemical methods are often harsh and unsuitable for direct use on protein-bound carbohydrates.

Purpose of the Study:

• To describe chemical methods for releasing sulfate esters from carbohydrate chains.
• To present techniques for monitoring the efficiency of sulfate ester release.
• To provide scalable procedures for preparative release of sulfate esters.

Main Methods:

• Release of sulfate esters via solvolysis.
• Monitoring solvolysis reaction efficiency.
• Acid and basic hydrolysis techniques for sulfate ester release.
• Scale-up procedures for solvolysis.

Main Results:

• Solvolysis effectively releases sulfate esters from carbohydrate chains.
• Methods for monitoring solvolysis efficiency are established.
• Acid and basic hydrolysis offer alternative routes for sulfate ester removal.
• Scalable solvolysis protocols are developed for larger material quantities.

Conclusions:

• Chemical methods, particularly solvolysis and hydrolysis, are essential for releasing sulfate esters when enzymes are unavailable.
• These methods enable the preparative analysis of sulfate ester modifications on carbohydrates, including protein-bound ones after release.
• The described techniques provide valuable tools for carbohydrate chemists and biochemists studying sulfated glycans.