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Method for peptide synthesis

A compound and amino acid technology, applied in the field of solid-phase peptide synthesis, can solve problems such as low coupling efficiency

Inactive Publication Date: 2009-09-02
LONZA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the present invention, the problem of low coupling efficiency is surprisingly solved by employing a side chain anchoring strategy

Method used

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  • Method for peptide synthesis
  • Method for peptide synthesis
  • Method for peptide synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Ile-Leu-Arg-Trp-Pro-Trp-Trp-Pro-Trp-Arg-Arg-Lys-NH 2 solid phase synthesis

[0057] All amino acids used in Example 1 are in L configuration. by mixing with Fmoc-chloride and 10% Na 2 CO 3 Reaction in dioxane / water (1:1), 33g of H-Lys(Boc)-NH 2 (from Genzyme) into Fmoc-Lys(Boc)-NH 2 . The side chain protecting Boc group was then removed with 50% trifluoroacetic acid (TFA) in dichloromethane at ambient temperature. After adding methyl tert-butyl ether, the Fmoc-Lys-NH 2 Precipitated as its TFA salt. The salt is recovered, dissolved in basic aqueous solution, and extracted to provide salt-free Fmoc-Lys-NH dissolved in the organic phase 2 .

[0058] 30 g of 2-chlorotrityl chloride polystyrene resin (from CBL-Patras) are added to the previously extracted organic phase and stirred in the presence of an organic base, preferably diisopropylethylamine. Reaction of the ε-amino groups with the resin, with a loading of about 0.50 mmol / g, yields the compound of...

Embodiment 2

[0062] Example 2: Ile-Leu-Arg-Trp-Pro-Trp-Trp-Pro-Trp-Arg-Arg-Lys-NH 2 solid phase synthesis

Embodiment 3

[0063] All amino acids used in Example 3 are in L configuration. 54 g of H-Lys(Boc)-NH 2 x HCl (from Genzyme) converted to Alloc-Lys(Boc)-NH 2 . The side chain protecting Boc group was then removed with hydrogen chloride in dichloromethane at 0°C. After the reaction, Alloc-Lys-NH 2 Precipitated as HCl salt. Filter and wash with dichloromethane. At elevated temperature and in the presence of diisopropylethylamine in N-methylpyrrolidone, 50 g of bromo-(4-methylphenyl)-methylpolystyrene resin (from CBL-Patras ) and 31.7 g of Alloc-Lys-NH 2 x HCl. Reaction of the ε-amino group with the resin, with a loading of about 0.55 mmol / g, yields the compound of formula IV

[0064]

[0065] Then, in the presence of sodium p-toluenesulfonate with Pd[PPh in N,N-dimethylformamide 3 ] 4 Treatment deprotects the compound of formula IV. The following steps were similar to those in Example 1, except that the coupling mixture used in each coupling step consisted of 1 equivalent of HO...

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Abstract

A new method of anchoring a growing peptide chain during chemical synthesis to a solid-phase support is devised. Novel amino acid derivatives and peptide derivatives, both unbonded and bonded to a solid-phase support, are also provided.

Description

technical field [0001] The present invention relates to the field of solid phase peptide synthesis, in particular to an improved method for constructing peptides by linking protected amino acids such as Fmoc-amino acids to the free N-terminus of extended peptides in solid phase synthesis. Background technique [0002] Larger amino acids, especially arginine, homoarginine and norarginine, are known to be more difficult to couple to expanding peptide chains than other amino acids. This problem exists with most commonly used coupling agents and is exacerbated in solid-phase synthesis, where the resin surface may present additional steric resistance. In general, this problem can be overcome by using higher than standard amounts of amino acids or oligopeptides to be coupled, especially by repeating coupling cycles. Of course, this method of using multiple reagents in excess will result in a large waste of expensive reagents. [0003] Di Bello et al. (Semisynth.Pept.Proteins, Pa...

Claims

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Application Information

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IPC IPC(8): C07K1/04C07K7/08C07K17/08
CPCC07K7/08C07K1/04
Inventor 马蒂厄·吉罗费尔南多·阿尔贝利西欧弗朗西斯卡·夸特里尼奥列格·韦布特斯基卡特娅·森迈克拉·维利讷
Owner LONZA LTD
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