Ionic liquid supported synthesis

Patent metadata

Field	Value
Publication number	US-10059736-B2
Application number	US-90848706-A
Country	US
Kind code	B2
Filing date	Mar 15, 2006
Priority date	Mar 15, 2005
Publication date	Aug 28, 2018
Grant date	Aug 28, 2018

Abstract

The present invention relates to ionic liquids for use in chemical applications and capable of serving the dual function of solvent and liquid support. The ionic liquid lends itself to a method of synthesizing oligomers selected from the group consisting of oligopeptides, oligosaccharides and oligonucleotides, comprising contacting a first monomer unit with an ionic liquid at reaction conditions to provide an ionic liquid bound monomer unit; and contacting the ionic liquid bound monomer unit with at least one further monomer unit at reaction conditions to provide an ionic liquid bound oligomer comprising from 2 to 30 monomer units. The method lends itself to large scale manufacture of oligopeptides, oligosaccharides and oligonucleotides.

First claim

What is claimed is:

1. A method of synthesizing an oligomer comprising:
a) contacting a monomer unit of an amino acid, a saccharide, or a nucleotide or nucleoside with an ionic liquid-support compound, to form an ionic liquid-supported monomer, wherein the ionic liquid-supported monomer comprises the ionic liquid-support compound covalently bonded to the monomer unit, wherein the ionic liquid-support compound is an organic salt comprising a heterocyclic or substituted heterocyclic quaternary nitrogen-containing organic cation, a heterocyclic or substituted heterocyclic quaternary phosphonium containing organic cation, or a heterocyclic or substituted heterocyclic trivalent sulfonium containing organic cation, and an anion balancing the charge on said organic cation;
b) contacting the ionic liquid-supported monomer with at least one further monomer unit of an amino acid, a saccharide, or a nucleotide at reaction conditions to provide an ionic liquid-supported oligomer that comprises the ionic liquid-support compound covalently bonded to an oligopeptide, oligosaccharide, or an oligonucleotide, wherein said ionic liquid-supported monomer and said at least one further monomer unit are solubilized in an organic solvent during said contacting;
c) optionally, contacting the ionic liquid-supported oligomer with at least one further monomer unit of an amino acid, a saccharide, or a nucleotide at reaction conditions; and
d) cleaving the ionic liquid-support compound from the ionic liquid-supported oligomer.

2. The method of claim 1 , further comprising repeating step c), a select number of times to yield a desired ionic liquid-supported oligomer.

3. The method of claim 2 , further comprising isolating the oligomer from the ionic liquid-support compound.

4. The method of claim 1 , wherein the organic cation is selected from the group consisting of N-substituted pyridine and 1,3-disubstituted imidazole.

5. The method of claim 1 , wherein the anion is selected from the group consisting of Cl − , Br − , BF 4 − , PF 6 − , SbF 6 − , CuCl 2 − , and AlCl 4 − .

6. The method of claim 1 , wherein the monomer units are amino acids.

7. The method of claim 1 , wherein the monomer units are nucleotides.

8. The method of claim 1 , wherein the monomer units are saccharides.

9. The method of claim 6 , wherein the oligomer comprises from 2 to 15 monomer units.

10. The method of claim 9 , wherein the oligomer comprises from 2 to 10 monomer units.

11. The method of claim 10 , wherein the oligomer comprises from 2 to 5 monomer units.

12. The method of claim 1 , wherein the ionic liquid-supported oligomer produced is solubilized in a polar organic solvent.

13. The method of claim 12 , wherein the oligomer is detached from the ionic liquid-supported compound and then separated from the polar organic solvent.

14. The method of claim 1 , wherein the oligomer is Leu 5 -enkephalin.

Assignees

• Chan Tak Hang
• Damha Masad J
• Miao Weishi
• Donga Robert Alexander
• He Xun
• Univ Mcgill

Inventors

• Chan Tak-Hang
• Damha Masad J
• Miao Weishi
• Donga Robert Alexander
• He Xun

Classifications

• C07K1/04

  on carriers {(C07K1/003, C07K1/006 take precedence)} · CPC title

• C07H3/06

  Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages · CPC title

• C07K1/023

  using racemisation inhibiting agents · CPC title

• C07H21/00 Primary

  Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids · CPC title

• Y02P20/542

  Cross-Sectional Technologies · mapped topic