Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – 4 to 5 amino acid residues in defined sequence
Patent
1998-08-17
2000-04-18
Moezie, F. T.
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
4 to 5 amino acid residues in defined sequence
530330, 530331, 514 17, 514 18, 514 19, A61K 3804
Patent
active
060516836
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The invention relates to medicine, specifically to methods of obtaining biologically active substances with immuno-regulating properties and can be used in medicine and veterinary science and in experimental biochemistry.
DESCRIPTION OF THE RELATED ART
Thymus extracts are widely used in applied medicine as immuno-regulators, specifically thymozin fraction 5/Goldstein A. L., Guna A., Latz M. M., Hardy H. A., White A./Thymolyn/CH.N 659586/. These extracts are comprised from a Polypeptide culture and their yield from natural sources is limited by the complexity of manufacture. Therefore the yield is not only limited in quantity but also inconsistent in physio-chemical and biological properties. Side effects have been observed in patients who used the polypeptide obtained from natural sources. Due to this, it become obvious for the need for synthetically obtained peptides. In the present time, synthetically synthesised line of peptide is available which possess immuno regulating properties: PCT WO 089/06134, EP N 230052.
U.S. Pat. No. 5,008,246, U.S. Pat. No. 5,013,723. Each synthetically obtained peptide which is limited in essential ingredients is highly active, low in toxicity, void of side effects which make it fit for use in medicine.
SUMMARY OF THE INVENTION
The invention relates to a new biologically active peptide with immuno-regulating properties of the formula X-Glu-Trp-Y, where X is H, Gly, Ala, Leu, Ile, Val, NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, .gamma.-aminobuteric acid, or .zeta.-aminocapronic acid; Y is Gly, Ala, Leu, Ile, Val NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, .gamma.-aminobuteric acid, .zeta.-aminocapronic acid, --OH, NH.sub.2, N.sub.2 H.sub.3, or a mono- or di-substituted amide (C.sub.1 -C.sub.3); with the proviso that when X is H, Y is not OH.
The invention also relates to a method of making the peptide and to the uses thereof.
DETAILED DESCRIPTION OF THE INVENTION
The question set out to be addressed is that of isolating a new biologically active peptide with immuno-regulating properties. D-Ile, D-Val, DNVal, D-Pro, D-Tyr, D-Phe, D-Trp, .gamma.-aminobuteric acid, or .zeta.-aminocapronic acid; D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, .gamma.-aminobuteric acid, OR .zeta.-aminocapronic acids, D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, Y-Aminobuteric acid, .zeta.-aminocapronic acid, --OH, NH.sub.2, N.sub.2 H.sub.3 or di-substituted amide (C.sub.1 -C.sub.3), with the proviso when X is H, Y is not OH.
The goal of the invention was to create a new technological process of creating a peptide. This peptide must be simple to produce and deliver a high quality yield.
The essence of the new method is the synthesis of the new peptide which takes place in a solution by successive growth of a chain from the C termination of the molecules, using a strategy of maximum blocking of functional groups, starting from amino acid alkyl ether, using the method of activating the ethers and the method of mixing anhydrides using tributyloxicarbonyl amino acid.
The peptide chain is outlined in the following table R f1in (chloroform-methanol-32% acetic acid=60:45:20) and R f2 in (butanol-pyridine-acetic acid=5:5:4:1).
TABLE 1 ______________________________________
PEPTIDE R f1 R f2
______________________________________
Abu-Glu-Trp-OH 0.40
0.56
Aca-Glu-Trp-OH 0.41 0.57
Ala-Glu-Trp-NH2 0.40 0.51
Arg-Glu-Trp-OH 0.26 0.48
D-Ala-Glu-Trp-OH 0.37 0.55
D-Ile-Glu-Trp-D-Phe 0.71 0.77
D-Ile-Glu-Trp-OH 0.39 0.54
D-Leu-Glu-Trp-NH2 0.35 0.56
D-Leu-Glu-Trp-OH 0.37 0.57
D-Val-Glu-Trp-OH 0.38 0.56
D-Phe-Glu-Trp-Ala 0.69 0.76
D-Pro-Glu-Trp-OH 0.58 0.72
D-Trp-Glu-Trp-OH 0.47 0.56
D-Tyr-Glu-Trp-OH 0.45 0.57
D-Val-Glu-Trp-NH2 0.43 0.53
Gly-Glu-Trp-Gly 0.44 0.49
Gly-Glu-Trp-OH 0.42 0.56
H-Glu-Trp-Abu 0.49 0.54
H-Glu-Trp-Aca 0.51 0.56
H-Glu-Trp-Arg 0.28 0.40
H-Glu-Trp-D-Ala 0.61 0.70
H-Glu-Trp-D-Ile 0.63 0.71
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Deigin Vladislav Isakovich
Korotkov Andrei Marxovich
Immunotech Developments Inc.
Moezie F. T.
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