IP Library › Granted Patent US 9,850,274
Granted Patent B2
US 9,850,274 · App. 13/142,931 · Granted Dec 26, 2017

Peptide combination

Inventor: Guenther Klett-Loch (Dielsdorf, CH)
Assignee: GKL-Biotec AG
C07K1/047C08G69/10Y02P20/55
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Quick Facts
Patent No.
US 9,850,274
App. No.
13/142,931
Granted
Dec 26, 2017
Kind
B2
Abstract

The invention relates to a peptide combination characterized by peptides each having the same sequence length (SEQL), that can be produced from a mixture (A) comprising a number x of amino acids having a protected acid group or a number z of peptides having an acid group protected by means of a protecting group and an activated amino group, wherein the amino acids are present in the mixture (A) in particular adjustable molar ratios, and a mixture (B) comprising a number y of amino acids having an amino group protected by means of a protecting group, wherein the amino acid molar ratios of the mixture (B) are equal to the amino acid molar ratios of the mixture (A), and wherein the number x=y.

Claims (29)

1. A combination of peptides comprising tetrapeptides, wherein the amino acids of said combination of peptides consist of a number x of different amino acids, wherein x is selected from 11 up to and including 18, and wherein said combination is produced by:

a) combining:

i) a first mixture (A) comprising said number x of-different amino acids having a protected acid group, and wherein the amino acids comprising at least aspartate, glutamate, proline, and glycine, wherein the amino acids are present in the first mixture (A) in certain, adjustable mole ratios, and wherein aspartate is present in 8.33 mol-%, glutamate is present in 9.53 mol-%, proline is present in 15.18 mol-%, and glycine is present in 37.10 mol-%; and,

ii) a first mixture (B) comprising said number x of amino acids having amino groups protected by means of protective groups, wherein the amino acid mole ratios in the first mixture (B) are equal to the amino acid mole ratios in the first mixture (A);

b) activating the protected amino functional groups of the resulting combination of peptides comprising dipeptides by cleavage of the amino protective groups, thereby producing a combination of peptides comprising dipeptides having protected acid groups and having activated amino groups;

c) combining:

i) a second mixture (A) comprising said combination of peptides comprising dipeptides having protected acid groups and having activated amino groups; and,

ii) a second mixture (B) comprising said number x of amino acids having amino groups protected by means of protective groups, wherein the amino acid mole ratios in the second mixture (B) are equal to the amino acid mole ratios in the second mixture (A);

d) activating the protected amino functional groups of the resulting combination of peptides comprising tripeptides by cleavage of the amino protective groups, thereby producing a combination of peptides comprising tripeptides having protected acid groups and having activated amino groups;

e) combining:

i) a third mixture (A) comprising said combination of peptides comprising tripeptides having protected acid groups and having activated amino groups; and,

ii) a third mixture (B) comprising said number x of amino acids having amino groups protected by means of protective groups, wherein the amino acid mole ratios in the third mixture (B) are equal to the amino acid mole ratios in the third mixture (A).

2. The combination of peptides of claim 1 , wherein the side chain functional groups of the amino acids are protected by means of protective groups.

3. The combination of peptides of claim 1 , wherein the combination of peptides is spiked with a mixture of natural amino acids in a ratio of 100 g+/−25 g tetrapeptides:80 g+/−20 g amino acid mixture.

4. A preparation comprising the combination of peptides of claim 1 , wherein said preparation is oncologically, immunologically, dermatologically, and/or endocrinologically effective.

5. A method for synthesizing a combination of peptides comprising tetrapeptides, wherein the amino acids of said combination of peptides consist of a number x of different amino acids, wherein x is selected from 11 up to and including 18, said method comprising:

a) combining:

i) a first mixture (A) comprising said number x of different amino acids having a protected acid group, and wherein the amino acids comprising at least aspartate, glutamate, proline, and glycine, wherein the amino acids are present in the first mixture (A) in certain, adjustable mole ratios, and wherein aspartate is present in 8.33 mol-%, glutamate is present in 9.53 mol-%, proline is present in 15.18 mol-%, and glycine is present in 37.10 mol-%; and,

ii) a first mixture (B) comprising said number x of amino acids having amino groups protected by means of protective groups, wherein the amino acid mole ratios in the first mixture (B) are equal to the amino acid mole ratios in the first mixture (A);

b) activating the protected amino functional groups of the resulting combination of peptides comprising dipeptides by cleavage of the amino protective groups, thereby producing a combination of peptides comprising dipeptides having protected acid groups and having activated amino groups;

c) combining:

i) a second mixture (A) comprising said combination of peptides comprising dipeptides having protected acid groups and having activated amino groups; and,

ii) a second mixture (B) comprising said number x of amino acids having amino groups protected by means of protective groups, wherein the amino acid mole ratios in the second mixture (B) are equal to the amino acid mole ratios in the second mixture (A);

d) activating the protected amino functional groups of the resulting combination of peptides comprising tripeptides by cleavage of the amino protective groups, thereby producing a combination of peptides comprising tripeptides having protected acid groups and having activated amino groups;

e) combining:

i) a third mixture (A) comprising said combination of peptides comprising tripeptides having protected acid groups and having activated amino groups; and,

ii) a third mixture (B) comprising said number x of amino acids having amino groups protected by means of protective groups, wherein the amino acid mole ratios in the third mixture (B) are equal to the amino acid mole ratios in the third mixture (A).

6. The method of claim 5 , wherein the side chain functional groups of the amino acids are protected by means of protective groups.

7. The method of claim 6 , wherein following the synthesis of the combination of peptides comprising tetrapeptides, the protected acid-, amino-, and side chain functional groups are activated by cleavage of the protecting groups, and in an intermediate step, the peptides are lyophilized and are mixed with a mixture of natural amino acids in aqueous solution, wherein the ratio of the peptides to the amino acid mixture is 100 g+/−25 g peptides: 80 g+/−20 g amino acid mixture, and/or the peptide-amino acid mixture is lyophilized in a following step.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE LAST NAME OF THE INVENTOR FROM KLETT-LOCK TO KLETT-LOCH PREVIOUSLY RECORDED ON REEL 027309 FRAME 0805. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT OF ASSIGNOR'S INTEREST. Recorded Mar 6, 2018
From: KLETT-LOCH, GUENTHER
To: GKL-BIOTEC AG
Reel/Frame 045812/0480 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2011
From: KLETT-LOCK, GUENTHER
To: GKL-BIOTEC AG
Reel/Frame 027309/0805 →
Priority Claims (1)
DE 10 2008 063 256 · Dec 30, 2008 · national
Continuity (1)
Related Publication 20120010149A1 · Jan 12, 2012