Solid phase synthesis technique for melanotan-II

A technology of solid-phase synthesis and solid-phase peptide synthesis, which is applied in the field of synthesis of melanotan-II, can solve the problems of difficult synthesis, harsh protection conditions, etc., and achieve the effect of easy synthesis and cheap raw materials

Active Publication Date: 2008-06-11
上海吉尔多肽有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To solve the problem that the existing cyclic polypeptide raw materials are difficult to synthesize or the conditions for deprotection are harsh, the task of the present invention is to select a group of protective group combinations to satisfy: (1) stability in polypeptide synthesis; (2) raw material It is easier to prepare; (3) at the same time, the selected protecting group can be removed under relatively mild conditions

Method used

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  • Solid phase synthesis technique for melanotan-II
  • Solid phase synthesis technique for melanotan-II
  • Solid phase synthesis technique for melanotan-II

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0072] Add 1 gram of the resin obtained in step 1 into the peptide bottle, add 10 ml of 2N NaOH / dioxane (1:4, volume ratio) and react at room temperature for 4 hours, and the resin is mixed with DMF / water (1:1 , for volume ratio) three times, DMF three times, methanol three times, 2% glacial acetic acid / methanol (1:1, volume ratio) three times, methanol three times, dichloromethane three times. Kaiser test resin is bluish purple.

[0073] Take half of the resin with trifluoroacetic acid: water: sulfide anisole: dithioethanol (92.5: 2.5: 2.5: 2.5), shake at room temperature for 2 hours, filter, wash the resin twice with trifluoroacetic acid, concentrate the filtrate, add anhydrous ether , yellowish solid. After repeated washing with anhydrous ether, 296 mg of the crude product Ac-Nle-Asp-His-D-Phe-Arg-Trp-Lys-NH was obtained.

[0074] Molecular weight: 1042.22 ESI: 1042.74 (M + )521.82 (M + +2H)HPLC: 47.63%

example 2

[0076] Add 1 gram of the resin obtained in step 1 into a peptide bottle, add 10 ml of 1N NaOH / dioxane (1:1, volume ratio) and react at room temperature for 2 hours, and obtain 85 mg of crude product by the same method as Example 1. ESI: 1043.17 (M + ) HPLC: 52.46%

example 3

[0078] Add 1 gram of the resin obtained in step 1 into a peptide bottle, add 10 ml of 1N NaOH / dioxane (1:3, volume ratio) and react at room temperature for 2 hours, and obtain 102 mg of crude product by the same method as Example 1. ESI: 1043.09 (M + )522.54 (M + +2H)HPLC: 67.59%

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Abstract

The invention relates to a synthesis method of melanotan-II, in particular to a solid-phase synthesis method of melanotan-II, which can resolve the problems of prior art which is hard to synthesize annular polypeptide and hard to remove protection. The invention forms ring on resin directly with simple reaction. The technical scheme of the invention comprises using Fmoc-Linker Amide AM Resin as carrier, connecting amino acids in turn accoriding to Fmoc / tBu solid polypeptide synthesis method, acetylizing, hydrolyzing NaOH solution and dioxane to remove trifluoroacetyl group and methyl ester on amino acids, using condenser to directly form ring on resin, and using the mixture of trifluroacetic acid, water, benzoylate sulfide and disulfide ethanol to cut off peptide from resin, to obtain crude melanotan-II, preparing HPLC purified transgenic acetate, freezing and drying to obtain acetate melanotan-II. The invention provides a method for simply synthesizing large-scale acetate melanotan-II.

Description

Technical field: [0001] The invention relates to a synthesis process of Melanotan-II, in particular to a solid-phase synthesis process of Melanotan-II. Background technique: [0002] Melanotan (Melanotan) is a synthetic peptide that can protect the skin. It is a copy of the natural alpha-MSH. Science professor Mac Hadlly discovered. Hadly proved through clinical experiments that Melanotan can make people's skin darken, but it does not affect hair. Dr. Norman Levine, a professor of dermatology, also came to the same conclusion through research. [0003] Although the synthetic Melanotan has a similar structure to the natural alpha-MSH, the effective effect of Melanton is 1000 times that of the natural alpha-MSH, and it can be more stable and last longer in the human body. Melanotan can stimulate black blood cells to produce melanin in the case of UV rays, because melanin is an important substance that prevents sun exposure and harmful UV rays from damaging skin cells and DNA...

Claims

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Application Information

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IPC IPC(8): C07K7/50C07K1/04
Inventor 徐红岩金健林
Owner 上海吉尔多肽有限公司
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