# US 11,299,590 B2 · Process for preparation of bioorganic nylon polymers and their use as antibacterial material

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- Number: US 11,299,590 B2
- Document ID: US11299590B2
- Status: Granted
- Kind: B2
- Application number: 16/060,751
- Filed: 2016-12-09
- Published: 2019-12-05
- Granted: 2022-04-12
- Earliest claimed: 2015-12-09
- Assignees: Universite De Montpellier; Centre National de la Recherche Scientifique (CNRS)
- Applicants: Universite De Montpellier; Centre National de la Recherche Scientifique (CNRS)
- Inventors: Jean Martinez; Ahmad Mehdi; Gilles Subra; Saïd Jebors
- Web page: https://patentgrep.com/patent/US11299590B2

## CPC

- C08G 69/36: derived from amino acids, polyamines and polycarboxylic acids
- C07K 17/08: the carrier being a synthetic polymer
- C08G 69/10: Alpha-amino-carboxylic acids {(polysuccinimides C08G73/1092)}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)

## Abstract

The present invention relates to new biopolymer, i.e. bioorganic nylons incorporating peptidic blocks obtained by a process of polymerization of amino peptidic blocks. The process of the invention comprises the steps of mixing amino peptidic blocks with or without a diaminoalcane and reacting the mixture according to polycondensation with a diacyl chloride in homogeneous or heterogeneous media.

## Claims

### Claim 1

A process for preparation of bioorganic nylon type polymers comprising the steps of
i) preparing a basic solution containing a peptidic amino-building block DanLysNHCH2CH2NH2 of the following formula:
and
a diamino building block F selected from the group consisting of diamino-alkane building block of general formula (F): H2N—Z—NH2,
wherein:
Z is (CH2)p; and
p is between 1 and 14,
ii) Initiating polymerization by contacting the solution of i) with a solution containing a diacyl G of the following formula (G): X(CO)—Y—(CO)X
wherein:
X is a halogen;
Y is (CH2)q;
q is between 1 and 12.

### Claim 2 (depends on 1)

The process of claim 1, wherein the diamino building block F is diamino hexane.

### Claim 3 (depends on 1)

The process of claim 1, wherein the diacyl G is adipoyl chloride.

### Claim 4 (depends on 1)

The process of claim 1, wherein:
Z is (CH2)p, C6H4, C6H4—W′—C6H4, C6F4, C6F4—W′—C6F4, or C10H6;
W′ is a bond, CH2, O, S, or Si2(CH2)5CH3]2
with s comprised between 1 and 4.

### Claim 5 (depends on 1)

The process of claim 1, wherein the polymerization is achieved in homogeneous or heterogeneous phase.

### Claim 6 (depends on 1)

The process of claim 1, wherein the polymerization is achieved in homogeneous phase and the peptidic amino-buildings block is dissolved in a solvent, which is also a solvent of the diacyl compound G.

### Claim 7 (depends on 1)

The process of claim 1, wherein the polymerization is achieved in heterogeneous phase and polymerization is initiated through interfacial polymerization.

### Claim 8 (depends on 1)

The process of claim 1, wherein the polymer is recovered and washed.

### Claim 9 (depends on 1)

The process of claim 1, wherein the basic solution of i) has a pH above 7.

### Claim 10 (depends on 1)

The process of claim 1, wherein the diacyl compound (G) is diacyl chloride.

### Claim 11 (depends on 1)

The process of claim 1, wherein the molar concentration of the peptidic-diamino building block varies from 1 to 100% and the molar concentration of diamino-alkane building block (F) is between 0 and 99%, the sum of both molar quantities being equal to 100% and corresponding to the molar quantity of diacyl compound (G) expressed as 100%.

### Claim 12 (depends on 1)

The process of claim 1, wherein a N-terminus of the peptidic amino-building block is protected by a protecting group selected from the group consisting of Fmoc, Boc, Cbz, Dde, trityl, NVoc, Alloc and Troc.

### Claim 13 (depends on 1)

The process of claim 1, wherein the peptidic amino-building block comprises, within a peptidic chain or at an N terminus or C-terminus, a lysine or an amino acid residue having a side chain that contains the following structure: —(CH2)m—NH2wherein m is between 0 and 10.

### Claim 14 (depends on 1)

The process of claim 1, wherein the peptidic amino-building block corresponds to a homo-or hetero-oligomer according to the following motif:
wherein:
n is comprised between 2 and 25;
R is the side chain of an amino-acid selected from the group consisting of natural aminoacids side chains, non-natural aminoacids side chains, and modified aminoacids side chains;
R′ is H or a C3-C6 alkyl linked to R thus forming a R—R′ ring; and d and e being such that d+e=0 to 10.

### Claim 15 (depends on 1)

The process of claim 1, wherein the peptidic amino-building block is labelled with a probe.