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Novel insulin derivates and preparation thereof

A technology of insulin derivatives and insulin, which is applied in the field of biomedicine and can solve problems such as separation difficulties

Inactive Publication Date: 2008-11-05
DALIAN NATIONALITIES UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This shows that only B29-Nε mono-modified insulin has available hypoglycemic activity, but according to the patent of this drug, the yield of B29-Nε mono-acylated insulin obtained is only 73%. and it is more difficult to separate
[0016] So far, the modification of the aliphatic chain of insulin is limited to the modification of the side chain or the N-terminal amino group, and no one has modified the carboxyl group and obtained a single modification with a yield of more than 80%

Method used

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  • Novel insulin derivates and preparation thereof
  • Novel insulin derivates and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of Novel Insulin Derivative C 18 h 37 NH-Thr-D:

[0039] Step 1. Fatty Amine C 18 h 37 NH 2 Preparation of:

[0040] Take 18 alcohol (C 18 h 37 OH) 27 grams (0.1 mole), add in the 500 milliliter round bottom flask that 300 milliliters of toluenes are housed, heat and evaporate 100 milliliters of toluene to take out the moisture in the alcohol. The remaining solution was added with pyridine in an equimolar amount to the fatty alcohol, refluxed and added dropwise thionyl chloride (SOCl 2 ), after the dropwise addition, the temperature was lowered to 90°C to continue the reaction for 4 hours, cooled, filtered to remove crystals, then evaporated toluene under reduced pressure, the residue was recrystallized with water and ethanol, and vacuum-dried by suction to obtain 25 grams of product, which is C 18 h 37 Cl. Dissolve this product in a small amount of anhydrous methanol and add it to a reactor that can be sealed and withstand a certain pr...

Embodiment 2

[0053] Example 2: C 14 h 29 Preparation of NH-Ala-D

[0054] Step 1. Fatty Amine C 14 h 29 NH 2 preparation of

[0055] Take 14 alcohol (C 14 h 29 OH) 18.5 grams (0.1 mole), add in the 500 milliliter round bottom flask that 300 milliliters of toluene is housed, heat and distill 100 milliliters of toluene to take out the moisture in the alcohol. The remaining solution was added with pyridine in an equimolar amount to the fatty alcohol, refluxed and added dropwise thionyl chloride (SOCl 2 ), after the dropwise addition, the temperature was lowered to 90°C to continue the reaction for 4 hours, cooled, filtered to remove the crystals, then evaporated toluene under reduced pressure, the residue was recrystallized with water and ethanol, and vacuum-dried by suction to obtain 17 grams of product, which is C 14 h 29 Cl. Dissolve this product in a small amount of anhydrous methanol and add it to a reactor that can be sealed and withstand a certain pressure, add excess liquid...

Embodiment 3

[0067] Example 3: C 16 h 33 Preparation of NH-Gly-D

[0068] Step 1. Fatty Amine C 16 h 33 NH 2 preparation of

[0069] Take 22 alcohol (C 16 h 33 OH) 24.2 grams (0.1 mole), add in the 500 milliliter round bottom flask that 300 milliliters of toluene is housed, heat and evaporate 100 milliliters of toluene to take out the moisture in the alcohol. The remaining solution was added with pyridine in an equimolar amount to the fatty alcohol, refluxed and added dropwise thionyl chloride (SOCl 2 ), after the dropwise addition, the temperature was lowered to 90°C to continue the reaction for 4 hours, cooled, filtered to remove the crystals, then evaporated toluene under reduced pressure, the residue was recrystallized with water and ethanol, and vacuum-dried by suction to obtain 22 grams of product, which is C 16 h 33 Cl. Dissolve this product in a small amount of anhydrous methanol and add it to a reactor that can be sealed and withstand a certain pressure, add excess liqu...

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Abstract

The invention relates to the biological field, in particular to a novel insulin derivative which is characterized in that the general formula of the compound is CnH2n + 1NH-X-D, wherein, n is equal to 14 to 22, CnH2n + 1NH is straight chain saturated fatty amino group; X is a natural amino acid except genetic coding proline or a 1-amino-1-carboxyl unnatural amino acid; D is a natural pig insulin stripped of B30 amino acid residue or a human insulin stripped of B30 amino acid residue. The insulin derivative of the invention is a novel derivative formed by connecting a fatty chain to the natural insulin or to the Alpha-carboxyl of the C-terminal residue on the parent B chain of the analogs. The preparation method is to take the natural pig insulin or human insulin as the starting material, cut off the first amino acid residue on the C terminal of the B chain of the insulin, and then take trypsin as the catalyst to cause the amino acid derivative connected with a fatty chain to become the novel insulin derivative connected with a fatty chain on the C terminal of B chain through enzymic reaction. The derivative has potential mouth taking and long-acting functions.

Description

1. Technical field: [0001] The invention relates to the field of biomedicine, in particular to insulin for diabetes, and also provides a preparation method thereof. 2. Background technology: [0002] Diabetes mellitus is a common multiple metabolic disease, and its incidence is on the rise both at home and abroad. According to incomplete statistics, there are more than 30 million people with diabetes in the country, and the incidence of diabetes is as high as 3.2%. Although many diseases can kill people, diabetes is the third leading cause of death. [0003] Insulin is a specific peptide hormone compound for the treatment of diabetes, and there is no more effective alternative drug so far. However, since insulin is a protein that is easily hydrolyzed by proteases in the gastrointestinal tract and loses its activity, it can only be used by injection and cannot be administered in other ways. For insulin-dependent patients, to maintain the normal metabolism of life, frequent...

Claims

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Application Information

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IPC IPC(8): C07K14/62C07K1/06C07K1/107C12P21/02
CPCY02P20/55
Inventor 何明磊
Owner DALIAN NATIONALITIES UNIVERSITY
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