Surface-bound fluorinated esters for amine capture

Patent metadata

Field	Value
Publication number	US-9422371-B2
Application number	US-201414531556-A
Country	US
Kind code	B2
Filing date	Nov 3, 2014
Priority date	Dec 21, 2006
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

A method for immobilizing an amino-containing material to a substrate is described. The method involves providing a tethering compound with two reactive groups: a substrate reactive group and a fluoroalkoxycarbonyl group. The method further involves preparing a substrate-attached tethering group by reacting the substrate reactive group of the tethering compound with a complementary functional group on the surface of a substrate. The substrate-attached tethering group has a fluoroalkoxycarbonyl group that can be reacted with an amino-containing material to form an immobilization group that connects the amino-containing material to the substrate.

First claim

We claim:

1. An article comprising a substrate comprising:
(a) an attached tethering group of Formula IV
—U—Y—(CO)—OCR 1 (R 2 ) 2   (IV)

that contains a fluoroalkoxycarbonyl group; and
(b) an attached immobilization group of Formula V
—U—Y—(CO)—NR 4 -T  (V)

wherein
U is equal to the reaction product of a substrate-reactive functional group X and a complementary group G on a surface of the substrate, wherein said substrate-reactive functional group X is linked to the Y on the compound of Formula (IV) and Formula (V) before the reaction and where X is selected from a carboxy, halocarbonyl, halocarbonyloxy, cyano, hydroxy, mercapto, isocyanato, halosilyl, alkoxysilyl, acyloxysilyl, azido, aziridinyl, haloalkyl, tertiary amino, disulfide, alkyl disulfide, benzotriazolyl, phosphono, phosphoroamido, or phosphato, wherein
group G is a hydroxy, mercapto, primary aromatic amino group, secondary aromatic amino group, or secondary aliphatic amino group when X is carboxy;
group G is a hydroxy, mercapto, primary aromatic amino group, secondary aromatic amino group, or secondary aliphatic amino group when X is halocarbonyl;
group G is a hydroxy, mercapto, primary aromatic amino group, secondary aromatic amino group, or secondary aliphatic amino group when X is halocarbonyloxy;
group G is an azido when X is cyano;
group G is a isocyanato or carboxy when X is hydroxy;
group G is a isocyanato, halocarbonyl, halocarbonyloxy, or ethylenically unsaturated group when X is mercapto;
group G is a hydroxy, mercapto, primary aromatic amino group, secondary aromatic amino group, secondary aliphatic amino group, or carboxylic acid group when X is isocyanato;
group G is a silanol group when X is halosilyl;
group G is a silanol group or metals having hydroxide groups on its surface when X is alkoxysilyl;
group G is a silanol group or metals having hydroxide groups on its surface when X is acyloxysilyl;
group G is a carbon-carbon triple bond, nitrile group, strained olefinic group when X is azido;
group G is a mercapto or carboxylic acid group when X is aziridinyl;
group G is a tertiary amino group when X is haloalkyl;
group G is a haloalkyl when X is tertiary amino;
group G is a metal when X is disulfide;
group G is a metal when X alkyl disulfide;
group G is a metal or metal oxide when X is benzotriazolyl;
group G is metal or metal oxide when X is phosphono;
group G is metal or metal oxide when X is phosphoroamido;
group G is metal or metal oxide when X is phosphate;

Y is a divalent group comprising an alkylene, heteroalkylene, arylene, or combination thereof and optionally further comprising an carbonyl, carbonyloxy, carbonylimino, oxy, —NR 3 —, or combination thereof;
R 1 is selected from hydrogen, fluoro, alkyl, or lower fluoroalkyl;
R 2 is a lower fluoroalkyl;
R 3 is hydrogen, alkyl, aryl, or aralkyl;
T is equal to the remainder of a primary or secondary biological amino-containing material of formula T-NHR 4 absent the amino group —NHR 4 wherein the biological amino-containing material is selected from the group consisting of an amino acid, peptide, DNA, RNA, protein, enzyme, organelle, immunoglobulin, and fragments of immunoglobulin; and
R 4 is selected from hydrogen, alkyl, or a portion of a ring structure connected to group T.

2. The article of claim 1 , wherein T is further associated with a second biological material.

3. The article of claim 1 , wherein Y is an alkylene or Y comprises a first alkylene connected to at least one other group selected from a heteroalkylene, arylene, second alkylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NR 3 —, or combination thereof.

4. The article of claim 1 , wherein Y is a heteroalkylene or Y comprises a first heteroalkylene connected to at least one other group selected from an alkylene, arylene, second heteroalkylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NR 3 —,or combination thereof.

5. The article of claim 1 , wherein Y is an arylene or Y comprises a first arylene connected to at least one other group selected from an alkylene, heteroalkylene, second arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NR 3 —, or combination thereof.

Assignees

• 3M Innovative Properties Co

Inventors

• Benson Karl E
• Leir Charles M
• Moore George G I
• Shah Rahul R

Classifications

• C07K17/14 Primary

  Peptides being immobilised on, or in, an inorganic carrier · CPC title

• C07H21/02

  with ribosyl as saccharide radical · CPC title

• G01N33/54353

  with ligand attached to the carrier via a chemical coupling agent (coatings G01N33/54393) · CPC title

• C07C323/52

  the carbon skeleton being acyclic and saturated · CPC title

• C07K1/1077

  by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids · CPC title