Bioactive peptide, preparation thereof and application thereof

A bioactive peptide, three-dimensional technology, applied in the field of chain heptapeptide, can solve the problems of limiting the research progress of marine bioactive peptide activity, purification, separation and identification difficulties, etc.

Inactive Publication Date: 2008-10-01
OCEAN UNIV OF CHINA
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  • Abstract
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Problems solved by technology

In addition, due to the small amount of natural products, it is difficult to purify, separate, and i

Method used

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  • Bioactive peptide, preparation thereof and application thereof
  • Bioactive peptide, preparation thereof and application thereof
  • Bioactive peptide, preparation thereof and application thereof

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Embodiment Construction

[0020] When the stereoabsolute configuration of the biologically active peptide of the present invention is (1S, 8R, 20S, 26R, 32S, 38S), it is named Tasiamide-D-Gln, and its preparation method comprises the following steps:

[0021] 1. The preparation of tetrapeptide fragment N-(tert-butoxycarbonyl)-L-isoleucine-glycine-N-methyl-D-phenylalanine-L-proline methyl ester, its sub-steps are as follows :

[0022]

[0023] Step a: methylate L-proline under the conditions of methanol and thionyl chloride. During operation, cool 50mL of methanol to -10°C, slowly drop into 13mL of thionyl chloride (SOCl 2 ), 5.75 g (50 mmol) L-proline (L-Pro-OH) was added after 25 min, and stirred at room temperature for 2 days. Thin-layer chromatography (TLC) showed that after the reaction was completed, the solvent was evaporated under reduced pressure, and then 25 mL of methanol was added to concentrate twice, and 100 mL of ether was added to the residue, ground in an ice-salt bath, and suction...

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Abstract

The invention relates to a biological bioactive peptide, and the molecular formula thereof is C42H67N7O10. When in preparation, tetrapeptide fragment N-(t-butoxycarbonyl)-L-isoleucine-N-methyl-D-phenylalanine-L-proline methyl ester is firstly prepared (t-butoxycarbonyl: BOC); then N-(9-fluorenylmethyloxycarbonyl)-N-methyl-glutamine is prepared (fluorenylmethyloxycarbonyl: Fmoc); then dipeptide fragment L-2-hydroxyl-3-methyl phocenic acid-O-benzyl salicylate-leucine is prepared; finally, the tetrapeptide fragment is detached from protecting groups and goes through condensation with N-(9-Fmoc)-N-methyl-glutamine, thus obtaining pentapeptide fragment N-(9-Fmoc)-N-methyl-glutamine-L-isoleucine-N-methyl-D-phenylalanine-L-proline methyl ester which goes through condensation after the dipeptide fragment and the pentapeptide fragment are detached from protecting groups. The biological bioactive peptide can provide sufficient raw materials and effective synthetic routes for the research of anti-tumor medicines and has a simple and convenient preparation method and easily controllable conditions.

Description

technical field [0001] The invention relates to a bioactive peptide, its preparation method and its application in antitumor. The bioactive peptide is a chain heptapeptide from the sea and has antitumor activity. Background technique [0002] Marine bioactive peptides are mostly derived from sponges, sea squirts, seaweeds and sea hares, etc. Their novel structures and remarkable biological activities have aroused great interest of synthetic chemists and medicinal chemists. However, active peptides from marine sources are mostly rich in N-methyl amino acids and other highly variable amino acids, which pose great challenges to synthetic chemists. [0003] Tasiamide is a structure isolated from the marine cyanobacterium Symploca sp. by the Moore group (Williams, P.G.; Yoshida, W.Y.; Moore, R.E.; Paul, V.J., J.Nat.Prod., 2002, 65, 1336-1339) Novel chain heptapeptide, its IC on KB and LoVo cells 50 The values ​​were 0.48 and 3.47 μg / mL, respectively, and the Moore team initiall...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/06A61P35/00
CPCY02P20/55
Inventor 李英霞李春霞马振华王鹏
Owner OCEAN UNIV OF CHINA
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