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EP0106522A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

A method for producing oligosaccharides by selectively cleaving glycosidic bonds with anhydrous hydrogen

Assignee: CHARLES F KETTERING FOUNDATION
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Filing: 1983-09-12
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Granted: —
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Expires: 2003-09-12
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Abstract

Abstract Anhydrous HF at low temperatures solvolyzes the different glycosidic linkages in a polysaccharide at widely varying rates such that oligosaccharides can be obtained from polysaccharides in higher yields than normal. The reaction is conveniently terminated and recovery of the oligosaccharide product is greaty facilitated by neutralizing excess HF with ether.

Inventors

  • 👤 Andrew James Mort

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-05 17:42
CPC Classifications
C; C07; C07H; C07H3/00; C07H3/06; C13; C13K; C13K13/00

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 106 words
A method for producing oligosaccharides which comprises; (a) reacting a polysaccharide with anhydrous, liquid HF at a reaction temperature less than 0°C at which temperature the glycosidic bonds forming said polysaccharide exhibit different rates of solvolysis in HF, (b) maintaining said liquid HF in contact with said polysaccharide at said reaction temperature for a time sufficient to selectively solvolyze said polysaccharide and produce oligosaccharides, (c) terminating said solvolysis without substantial solvolysis of the oligosaccharides produced in step (b) by quenching said reaction by the addition of an organic solvent and/or by neutralizing said HF with a neutralizing agent, and (d) separating oligosaccharides from the reaction products.
Claim 2
Independent Claim 106 words
A method for producing oligosaccharides which comprises; (a) reacting a polysaccharide with anhydrous, liquid HF at a reaction temperature less than 0°C at which temperature the glycosidic bonds forming said polysaccharide exhibit different rates of solvolysis in HF, (b) maintaining said liquid HF in contact with said polysaccharide at said reaction temperature for a time sufficient to selectively solvolyze said polysaccharide and produce oligosaccharides, (c) terminating said solvolysis without substantial solvolysis of the oligosaccharides produced in step (b) by quenching said reaction by the addition of an organic solvent and/or by neutralizing said HF with a neutralizing agent, and (d) separating oligosaccharides from the reaction products.
Claim 3
Independent Claim 12 words
The method of claim l,wherein said reaction temperature is less than -20°C.
Claim 4
Dependent Claim 31 words
The method of claim 2 wherein said solvolysis is terminated by quenching the products of said reaction with an organic solvent which neutralizes said H F and from which oligosaccharides precipitate.
Claim 5
Dependent Claim 16 words
The method of claim 3,wherein said solvolysis is terminated by contacting the reaction products with ether.
Claim 6
Dependent Claim 19 words
The method of claim 3,wherein said solvent is the same temperature as said reaction temperature or a lower temperature.
Claim 7
Dependent Claim 12 words
The method of claim 1,wherein said reaction temperature is less than -40°C.
Claim 8
Dependent Claim 24 words
The method of claim 1,wherein said organic solvent and/or said neutralizing agent is added to said reaction as a slurry with dry ice. ,
Claim 9
Independent Claim 11 words
The method of claim l,wherein said organic solvent is ethyl ether.
Claim 10
Dependent Claim 12 words
The method of claim 8 wherein said neutralizing agent is calcium carbonate.
Claim 11
Independent Claim 115 words
A method for selectively cleaving the polysaccharide produced by R.Japonicum 31 lb138 which comprises: (a) reacting the polysaccharide produced by R.Japonicum 31 lb138 with anhyarous, liquid HF at a reaction temperature less than 0°C, at which temperature the glycosidic bonds forming said polysaccharide exhibit different rates of solvolysis in HF, (b) maintaining said liquid HF in contact with said polysaccharide at said reaction temperature for a time sufficient to selectively solvolyze said polysaccharide and produce oligosaccharides, (c) terminating said reaction without substantial solvolysis of the oligosaccharides produced in step (b) by quenching said reaction with the addition of an organic solvent and/or by neutralizing said HF, and (d) separating said oligosaccharides from the reaction products.
Claim 12
Independent Claim 115 words
A method for selectively cleaving the polysaccharide produced by R.Japonicum 31 lb138 which comprises: (a) reacting the polysaccharide produced by R.Japonicum 31 lb138 with anhyarous, liquid HF at a reaction temperature less than 0°C, at which temperature the glycosidic bonds forming said polysaccharide exhibit different rates of solvolysis in HF, (b) maintaining said liquid HF in contact with said polysaccharide at said reaction temperature for a time sufficient to selectively solvolyze said polysaccharide and produce oligosaccharides, (c) terminating said reaction without substantial solvolysis of the oligosaccharides produced in step (b) by quenching said reaction with the addition of an organic solvent and/or by neutralizing said HF, and (d) separating said oligosaccharides from the reaction products.
Claim 13
Dependent Claim 13 words
ll. The method of claim 10,wherein said reaction temperature is less than -20°C.
Claim 14
Dependent Claim 26 words
The method of claim 11,wherein said solvolysis reaction is terminated by quenching with an organic solvent which neutralizes said HF and from which said oligosaccharides precipitate.
Claim 15
Dependent Claim 17 words
The method of claim 12,wherein said solvolysis is terminated by contacting the reaction products with ethyl ether.
Claim 16
Dependent Claim 24 words
The method of claim 10,wherein said organic solvent and/or said neutralizing agent is added to said reaction products as a slurry in dry ice.
Claim 17
Dependent Claim 12 words
The method of claim 10,wherein said reaction temperature is less than -40°C.

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