Sulfuryl hypo-phosphono hybridation peptide and preparation method thereof

A technology of sulfonylphosphinate and hybrid peptide, which is applied in the field of sulfonylphosphinate hybrid peptide and its preparation, and can solve the problem that there is no sulfonylphosphinate hybrid peptide yet.

Inactive Publication Date: 2012-07-25
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are only sulfonyl peptides and phosphinyl peptides and reports on their synthesis, but there is no report on sulfonylphosphinyl hybrid peptides composed of sulfamic acid, phosphoramidophosphorous acid and aminocarboxylic acids and their synthesis

Method used

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  • Sulfuryl hypo-phosphono hybridation peptide and preparation method thereof
  • Sulfuryl hypo-phosphono hybridation peptide and preparation method thereof
  • Sulfuryl hypo-phosphono hybridation peptide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation of N-[N-[N-Benzyloxycarbonylaminoethanesulfonyl]amino-(4-methylphenyl)-benzylphosphinoyl]glycine ethyl ester (1a)

[0048]

[0049]Dissolve 0.49g (1.9mmol) of Cbz-protected taurine in 10mL of anhydrous acetonitrile (slightly heat to promote dissolution), and then add 0.24g (2.0mmol) of p-tolualdehyde and 0.358g (2.0mmol) of benzene Phosphine dichloride, stirred at 45°C for 12h. After the reaction, add 0.824g (8mol) ethyl glycine, stir for 10min and add 1.4mL (0.808g, 8mmol) Et 3 N, after continuing to react for 24h, spin dry acetonitrile. 50 mL of ethyl acetate was added, and the organic phase was washed with 50 mL of saturated NaHCO 3 Wash three times with aqueous solution, wash twice with saturated saline, wash three times with 0.1mol / L citric acid aqueous solution, and wash twice with saturated NaCl aqueous solution. Dry over anhydrous sodium sulfate and spin dry to obtain a yellow viscous oil, add a small amount of ethyl acetate to crystallize in t...

Embodiment 2

[0051] Preparation of N-[N-[N-Benzyloxycarbonylaminoethanesulfonyl]amino-(4-methylphenyl)-benzylphosphinoyl]glycine ethyl ester (1a)

[0052] According to the method described in Example 1, when adding 0.619g (2.4mmol) Cbz protected taurine amide, then adding 0.324g (2.7mmol) p-tolualdehyde and 0.483g (2.7mmol) phenyl dichloro Phosphine. When 1.116 g (8 mol) of glycine ethyl ester hydrochloride was added after the first step of reaction for ammonolysis, the yield was 30%.

Embodiment 3

[0054] Preparation of N-[N-[N-Benzyloxycarbonylaminoethanesulfonyl]amino-(4-methylphenyl)-benzylphosphinoyl]glycine ethyl ester (1a)

[0055] According to the method described in Example 2, when 0.824 g (8 mol) ethyl glycine was added for ammonolysis, the yield was 43%.

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Abstract

The invention provides a sulfuryl hypo-phosphono hybridation peptide and a preparation method thereof. The sulfuryl hypo-phosphono hybridation peptide has a structure represented by the formula (1), is formed by condensing sulfamic acid, amino phosphinic acid and amino acid, and can be used as medicament, enzyme inhibitor, antibacterialagent, hapten for preparing bzyme, and the like. The sulfurylhypo-phosphono hybridation peptide can be prepared in such a way that sulfamide, aldehyde or ketone, alkyl or aryl phosphine oxide react in organic solvent for a period of time, amino-acid ester or salt thereof is added in the reaction mixture in the presence of alkaline to carry out ammonolysis. The method has simple and easy-obtained materials, simple process, high synthesis efficiency, is an atomic and economic gathering-type synthesis method and can be used for preparing optical active sulfuryl hypo-phosphono hybridation peptide.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, biomolecules and organic synthesis, and specifically relates to a sulfonylphosphinyl hybrid peptide and a preparation method thereof. Background technique [0002] Sulfonyl peptides and phosphinoyl peptides are polypeptide substances containing sulfamic acid and phosphoramidite respectively. Because they contain aminosulfonic acid and aminophosphinic acid with tetrahedral structure respectively, they can be used to simulate the transition state of ester bond and amide bond hydrolysis, and have been widely used in enzyme inhibitor research in recent years (Xu Jiaxi, Organic Chemistry, 2003, 23, 1-9; Moree, W.J.; van der Marel, G.A.; van Boom, J.H.; Liskamp, ​​R.M.J. Tetrahedron 1993, 49, 11055-11064) and antiparasitic drug research (Ravaschino, E.L.; Docampo, R.; Rodriguez, J.B.J. Med. Chem. 2006, 49, 426-435). [0003] Sulfonyl peptide mainly prepares sulfamoyl chloride by protected s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/36
Inventor 许家喜贺凤丹孟凡华
Owner BEIJING UNIV OF CHEM TECH
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