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Molecular spacer, production method thereof and uses of same on an analysis chip with molecules or biomolecules

A technology of biomolecules and spacer arms, applied to biochips and microsystems for bioanalysis, biochips, application fields on analysis chips

Inactive Publication Date: 2007-02-28
COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although more effective than other earlier prior art spacers, it is not possible for this spacer to solve all of the above problems simultaneously

Method used

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  • Molecular spacer, production method thereof and uses of same on an analysis chip with molecules or biomolecules
  • Molecular spacer, production method thereof and uses of same on an analysis chip with molecules or biomolecules
  • Molecular spacer, production method thereof and uses of same on an analysis chip with molecules or biomolecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A

[0099] Example A: Activation of oligosaccharides (Reaction A)

[0100] In this example, an ozone decomposition reaction was used. The method used is described in [5].

[0101] The sugar (1) (0.93 mmol) allylated at the anomeric position was dissolved in a mixture of 5 ml of dichloromethane and methanol (1 / 1): the medium was immersed in a cold bath (acetone + Dry ice). Then the ozone O 3 Bubbling into the solution: As soon as blue (characteristic of excess ozone) appears, replace ozone with argon (or nitrogen). When the reaction is complete, by adding dimethyl sulfide Me 2 S (4.65mmol, 5eq) reduced the medium: DMSO was then formed. After overnight, the medium slowly returned to ambient temperature and then evaporated under vacuum: the organic residue was diethyl ether Et 2 O was extracted and then washed with water. The organic phase was evaporated under vacuum and then co-evaporated with toluene. The crude product was purified by silica gel column chromatography (eluent: petroleum...

Embodiment B

[0103] Example B: Reduction of Nitriles (Reaction B)

[0104] The method used is described in [6].

[0105] LiAlH 4 (381mg, 10.03mmol, 1eq) was added to freshly distilled diethyl ether (20ml).

[0106] 4-Pentenenitrile (3) (814 mg, 1 ml, 10.03 mmol) was slowly added to the reaction medium with a temperature of 0° C. (ice bath) and stirring under a nitrogen atmosphere. The stirring must be continued for approximately 20 minutes at ambient temperature.

[0107] Next, add water (0.4ml), then a 20% aqueous sodium hydroxide solution (0.3ml), and finally another amount of water (1.4ml): these additions must be carried out with great care, because the neutralization effect may be severe . When the diethyl ether solution is separated from the inorganic white residue by precipitation, the supernatant is extracted.

[0108] The white solid (residue) was washed twice with diethyl ether, and the organic phases were combined. A 3M hydrochloric acid HCl solution was added to the organic phase i...

Embodiment C

[0115] Example C: Reductive amination (Reaction C)

[0116] The chemical method used is described in [7].

[0117] The aldehyde (2) (20.87mmol) is dissolved in the calcium hydride (CaH 2 ) In freshly distilled dimethylformamide (1.2ml): stir the medium and add amine (4) (31.30mmol, 2eq). After about 20 minutes, add sodium cyanoborohydride NaBH 3 CN (83.47 mmol, 4 eq) was added to the mixture, and the mixture was continuously stirred at ambient temperature overnight.

[0118] If the reaction is not complete, you can add NaBH 3 CN(1eq). Then, when the reaction was completed, pyridine (2.4 ml) and acetic anhydride (83.47 mmol, 2 eq / amine) were added to the mixture.

[0119] When the reaction was complete (about 1 hour after the addition), the crude compound was extracted with diethyl ether and water. Use magnesium sulfate (MgSO 4 ) Dry, then filter, evaporate under vacuum, and then co-evaporate with toluene.

[0120] The compound (5) was then purified by silica gel chromatography (el...

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PUM

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Abstract

The invention relates to a molecular spacer, to a method of fixing a molecular unit to a solid support and to the use of said spacer on analysis chips with molecules or biomolecules. According to the invention, the spacer has formula (I) wherein: X<0>, X<4> = C, O, S, Se, N, P, As; X<1-3 >= C, O, N, S, Se, P, As, or aryl, heteroaryl at C1-6; Z<1-2 >= C-R, Si-R, N, P and As, where R = alkyl at C1-6; R<1-3 >= H, or alkyl, aryl, heteroaryl at C1-6; [Gp] = protective group of >N; n, m and n = integers = 1; [Sup] = H or a silanised solid support; and [mo] = H or a molecular unit which is intended to be fixed covalently by means of the spacer to the silanised solid support.

Description

Technical field [0001] The present invention relates to a molecular spacer, a method for preparing a spacer for connecting a molecular unit to a solid phase carrier, and the application of this spacer on an analysis chip containing molecules or biomolecules. [0002] In the following disclosure, the marks between square brackets [] refer to the references listed at the end of the specification. [0003] The analysis chip targeted by the present invention is more specifically, but not exclusively, a biochip and a microsystem for bioanalysis. They can be divided into three categories: DNA chip, lab-on-chip and cell-on-chip. [0004] Currently, a new type of chip has emerged: glycochip. This kind of biochip is either the result of the deposition of natural or synthetic substances, or the result of multi-step parallel synthesis (combinatorial chemistry) supported by various oligosaccharide sequences. Oligosaccharides exhibit certain broad types of endogenous sugar conjugation. The mol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/02G01N33/543
CPCG01N33/54353C07H3/02Y02P20/55
Inventor 韦罗妮克·佩雷蒂弗朗索瓦丝·维内达维德·博纳夫
Owner COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES
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