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Organic ammonium salt and hydrogen-bonding material treatment agent using same

A technology of organic ammonium salts and ammonium salts, applied in the field of hydrogen-bonding material treatment agents, can solve the problems of unsuitable, unsuitable solid substances, difficult to preserve biological samples, etc., and achieve excellent dispersibility and excellent maintenance of three-dimensional structure , excellent solubility or dispersibility

Pending Publication Date: 2022-07-08
MIYOSHI OIL & FAT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the room temperature liquid ionic liquid has excellent affinity and preservation with biological samples, it is not suitable for applications requiring solid substances at room temperature, for example, it is not suitable for clinical diagnostic reagents or biosensors, etc., and needs further improvement
In addition, in the case of storage in a liquid state, it is difficult to store biological samples at high concentrations from the viewpoint of the solubility of biological samples and liquids.
Therefore, although freeze-drying or cryopreservation can be used as a solid state, there is a problem that the long-term stabilization effect of biological samples is low.
[0007] As an example of a solid enzyme stabilizer, an example using a plant-derived polypeptide as a hydrolyzate such as soybeans is disclosed (Patent Document 6), but the stabilizing effect is not sufficient

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0295] Synthesis of Compound 1

[0296] Compounds represented by the following formula were synthesized.

[0297]

[0298] Triethanolamine (19.11 g, 0.128 mol) and formic acid (5.89 g, 0.128 mmol) were reacted in 100 mL of water at room temperature for 3 hours, and then the water was distilled off under reduced pressure to obtain a pale yellow solid. By washing the obtained solid, Compound 1 (triethanolamine formate) was obtained as a white solid.

[0299] FT-IR (KBr): 3360cm -1 : O-H stretching vibration 2950cm -1 : C-H stretching vibration 1558cm -1 : COO - stretching vibration

[0300] 1 H-NMR (D 2 O 400MHz): δ3.31 (t, 6H, N + C H 2 CH 2 OH), δ3.85(t, 6H, N + CH 2C H 2 OH), δ8.36 (s, 1H, H COO - ).

[0301] 13 C-NMR (D 2 O 100MHz): δ55.4 (N + C H 2 CH 2 OH), δ55.6 (N + CH 2 C H 2 OH), δ171.0 (H C OO - ).

Embodiment 2～87

[0303] Compounds 2 to 87 of Examples 2 to 87 shown in Tables 1 to 5 were synthesized by the same synthesis method as in Example 1 and in accordance with the blending molar ratios described in Tables 7 to 9. The physical property values ​​are shown as follows.

Embodiment 2

[0304] Synthesis of Compound 2

[0305]

[0306] FT-IR (KBr): 3388cm -1 : O-H stretching vibration 2922cm -1 : C-H stretching vibration 1543cm-1: COO - stretching vibration

[0307] 1 H-NMR (D 2 O 400MHz): δ0.73-0.77 (m, 3H, NH 3 + C(CH 2 OH) 2 CH 2 C H 3 ), δ1.50-1.56 (m, 2H, NH 3 + C(CH 2 OH) 2 C H 2 CH 3 ), δ1.84(s, 3H, C H 3 COO - ), δ3.49-3.50 (m, 4H, NH 3 + C(C H 2 OH) 2 CH 2 CH 3 ).

[0308] 13 C-NMR (D 2 O100MHz): δ6.3 (NH 3 + C(CH 2 OH) 2 CH 2 C H 3 ),δ23.2(NH 3 + C(CH 2 OH) 2 C H 2 CH 3 ),δ23.3( C H 3 CO - ),δ60.5(NH 3 + C (CH 2 OH) 2 CH 2 CH 3 ), δ63.3 (NH 3 + C( C H 2 OH) 2 CH 2 CH 3 ), δ181.4 (CH 3 C OO - ).

[0309]

[0310] FT-IR (KBr): 3145cm -1 : O-H stretching vibration 2946cm -1 : C-H stretching vibration 1572cm -1 : COO - stretching vibration

[0311] 1 H-NMR (D 2 O 400MHz): δ1.84(s, 3H, C H 3 COO － ),δ3.57(s,6H,NH 3 + C(C H 2 OH) 3 ).

[0312] 13 C-NMR (D 2 O 100MHz):...

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Abstract

Provided are: a novel compound useful for various treatments of a hydrogen-bonding material such as a biological sample; and a hydrogen-bonding material treatment agent. The present invention is an organic ammonium salt and a hydrogen-bonding material treatment agent containing the organic ammonium salt. Wherein the organic ammonium salt is in a solid state at 25 DEG C and contains an anion and an ammonium cation represented by formula (I): N + RnH4-n (I) (in formula (I), each R independently represents a hydroxyalkyl group or the like, the hydroxyalkyl group has one or more hydroxyl groups, the alkyl moiety is a C1-10 linear chain or branched chain, and the alkyl moiety may contain an oxygen atom. And n represents an integer of 0-4. ).

Description

technical field [0001] The present invention relates to an organic ammonium salt and a hydrogen-bonding material treating agent using the organic ammonium salt. Background technique [0002] Biocatalysts such as enzymes or yeast, and biological samples such as peptides, proteins, nucleic acids, or insoluble polysaccharides such as cellulose, are often affected by temperature, pH, solvent, or electrostatic repulsion between molecules, and the three-dimensional structure of the molecules is easily changed. Destruction reduces the activity, that is, the catalytic ability. Therefore, it is necessary to maintain the three-dimensional structure of the active site and the three-dimensional structure of the amino acid residue when it is used for the preservation of the biocatalytic ability and biocatalytic reaction, or when the biological sample is preserved. [0003] As methods for long-term storage of biocatalysts and biological samples, freeze-drying methods in a powder state and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/08
CPCC07C215/12C07C215/10C07C215/08C12N9/96C07C69/24C07C69/675C07C69/40A01N1/00C12N1/04C12Q1/6806
Inventor 金子恒太郎河合功治
Owner MIYOSHI OIL & FAT
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