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Electrochemical deblocking solution for electrochemical oligomer synthesis on an electrode array

a technology of electrochemical oligomer and electrode array, which is applied in the direction of bulk chemical production, liquid/fluent solid measurement, peptides, etc., can solve the problems of deblocking solution, inability to aqueous deblock solution, and less desirable

Inactive Publication Date: 2007-02-15
CUSTOMARRAY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention provides an electrochemical deblock solution for use in the synthesis of various oligomers or polymers. The solution involves an organic solvent-based deblocking step that allows for the removal of blocking moieties on a molecule to allow for covalent binding of a next \"mer\" in the synthesis process. The deblock solution can be applied to a variety of chemical functional groups on the attached molecule using an electrode microarray. The invention provides a more efficient and effective method for deblocking compared to previous methods, making the synthesis process faster and more efficient."

Problems solved by technology

The organic solvent provides a deblocking solution where an aqueous deblock solution cannot be used or is less desirable owing to better performance using an organic based deblocking solution.

Method used

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  • Electrochemical deblocking solution for electrochemical oligomer synthesis on an electrode array
  • Electrochemical deblocking solution for electrochemical oligomer synthesis on an electrode array
  • Electrochemical deblocking solution for electrochemical oligomer synthesis on an electrode array

Examples

Experimental program
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Effect test

example 1

[0128] One preferred deblocking solution comprises 1 M hyrdroquinone, 10 mM benzoquinone, 50 mM tetraethyl ammonium p-toluene sulfonate, 5 mM 2,6-lutidine, 20% methanol, 80% acetonitrile. The solution is made by first mixing the methanol and acetonitrile. After adding all components, approximately one liter of solution was obtained because there was a significant increase in volume owing to the amount of hydroquinone in solution. Benzoquinone was added first, then hydroquinone, then the salt, and then lutidine. The benzoquinone was added first because it will not dissolve adequately if not added first. The solution was mixed using a stir bar on a stir plate. Mixing was performed until all components were dissolved. Mixing continued until the solution was required to be used.

example 2

[0129] Electrochemical deblocking solutions were made in accordance with the present invention to test the effectiveness of organic base for confinement of deblocking to the anodes. The procedure comprised using the coupling of Cy3 (fluorescent) phosphoramidite to detect the efficiency and quality of dimethoxytrityl (DMT) removal by acid generated electrochemically in the presence of an electrochemical deblocking solution containing selected amounts of lutidine. Specifically, electrode microarray chips were initialized with a 5-mer oligonucleotide containing a DMT blocked 5′ hydroxyl group. Acid was generated electrochemically over specific electrodes to remove the DMT blocking group in the presence of varying amounts of lutidine. A Cy3 phosphoramidite was coupled to any non-DMT-blocked 5′ hydroxyls allowing one to visualize electrochemical deblocking using a fluorescent microscope.

[0130] The same oligonucleotide was synthesized at each electrode (ACTGT, 5′→3′). The DMT was left on...

example 3

[0132] Electrochemical deblocking solutions were made in accordance with the present invention to test the effectiveness of organic base for confinement of deblocking to the anodes. The procedure comprised using the coupling of Cy3 phosphoramidite to detect the efficiency and quality of dimethoxytrityl (DMT) removal by acid generated electrochemically with electrochemical deblocking solution containing selected amounts of lutidine. Specifically, electrode microarray chips were initialized with a 5-mer oligomer containing a DMT blocked 5′ hydroxyl. Acid was generated electrochemically over specific electrodes to remove the DMT in the presence of varying amounts of lutidine. A Cy3 phosphoramidite was coupled to any non-DMT-blocked 5′ hydroxyls allowing one to visualize electrochemical deblocking using a fluorescent microscope.

[0133] The same oligonucleotide was synthesized at each electrode (ACTGT, 5′→3′). The DMT blocking group was left on the final “A” nucleotide base for testing t...

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Abstract

There is disclosed an electrochemical deblocking solution for use on an electrode microarray. There is further disclosed a method for electrochemical synthesis on an electrode array using the electrochemical deblocking solution. The solution and method are for removing acid-labile protecting groups for synthesis of oligonucleotides, peptides, small molecules, or polymers on a microarray of electrodes while substantially improving isolation of deblocking to active electrodes. The method comprises applying a voltage or a current to at least one electrode of an array of electrodes. The array of electrodes is covered by the electrochemical deblocking solution.

Description

TECHNICAL FIELD OF THE INVENTION [0001] The present invention relates to an electrochemical deblocking solution and method on an electrode microarray for removing acid-labile protecting groups. The present invention is particularly useful for synthesis of oligonucleotides, peptides, small molecules, branched polymers, or other polymers on an electrode array device having short distances between neighboring electrodes. BACKGROUND OF THE INVENTION [0002] Rapid developments in the field of DNA microarrays have lead to a number of methods for synthetic preparation of DNA. Such methods include spotting pre-synthesized oligonucleotides, photolithography using mask or maskless techniques, in situ synthesis by printing reagents, and in situ parallel synthesis on a microarray of electrodes using electrochemical deblocking of protective groups. A review of oligonucleotide microarray synthesis is provided by: Gao et al., Biopolymers 2004, 73:579. The synthetic preparation of a peptide array wa...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C12Q1/68C25B3/23C25B3/25C25B3/29
CPCB01J19/0046C07H21/04B01J2219/00653Y02P20/55C07H21/02C07D213/16C25B3/00C25B3/29C25B3/23C25B3/25G01N33/00G01N33/0003C07B31/00C07B33/00C07C39/08C07C50/04C07B41/02C07B41/06C07C50/00C07C309/30
Inventor MAURER, KARLCOOPER, JOHN J. JR.STRATHMANN, MICHAEL
Owner CUSTOMARRAY
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