Solid support with a grafted chain
View Patent ↗Articles that contain a solid support with a grafted chain extending from the solid support, methods of making these articles, and various uses of the articles are described. More specifically, the grafted chain has a functional group that can react with or interact with target compound. Alternatively, the functional group on the grafted chain can react with a modifying agent to provide another group that can react with or interact with the target compound. The grafted chains are attached to the solid support through a ring-opened azlactone group. The articles can be used to purify the target compound or to separate the target compound from other molecules in a sample.
1. An article comprising a modified grafted support of Formula (V)
SS-(CO)—NH—C(R 1 ) 2 —(CH 2 ) p —(CO)-Q-Y 1 -Q-(CO)—CR 2 U 4 —CH 2 —U 3 (V)
wherein
SS comprises a solid support;
p is an integer equal to 0 or 1;
each R 1 is each independently selected from alkyl, heteroalkyl, aryl, or aralkyl;
Y 1 is a first linking group comprising an alkylene, heteroalkylene, arylene, or combination thereof;
each Q is independently a divalent group selected from oxy, thio, or —NR 3 — where R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl;
each R 2 is independently hydrogen or an alkyl;
U 3 comprises at least one divalent monomeric unit of formula CR 2 (Y 2 L-T)-CH 2 —;
Y 2 is a second linking group selected from a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combination thereof;
U 3 includes at least one divalent monomeric unit of formula —CR 2 (Y 2 L-T)-CH 2 —;
U 4 is hydrogen or comprises at least one divalent monomeric unit of formula —CR 2 (Y 2 L-T)-CH 2 —;
L is an attachment group formed by reacting group Z 1 with a modifying group A of a modifying agent A-T;
Z 1 is a functional group selected from (1) an acidic group or a salt thereof, (2) an amino group or a salt thereof, (3) a hydroxyl group, (4) an azlactone group or a precursor of the azlactone group, (5) a glycidyl group, or (6) a combination thereof; and
T is a remainder of the modifying agent A-T and is equal to the modifying agent A-T minus the modifying group A.
2. The article of claim 1 , wherein the solid support is in the form of a bead.
3. The article of claim 1 , wherein the solid support comprises a crosslinked polymeric material.
4. The article of claim 1 , wherein Z 1 is an acidic group and the modifying agent is of formula
wherein
D is oxy, thio, or —NR 3 —;
R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl; and
each R 4 is independently hydrogen, alkyl, heteroalkyl, aryl, or aralkyl.
5. The article of claim 1 , wherein Z 1 is a hydroxyl group and the modifying agent is of formula
wherein
D is oxy, thio, or —NR 3 —;
R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl;
each R 4 is independently hydrogen, alkyl, heteroalkyl, aryl, or aralkyl; and
X is halo.
6. The article of claim 1 , wherein Z 1 is an amino group and the modifying agent is of formula
wherein
D is oxy, thio, or —NR 3 —;
R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl;
each R 4 is independently hydrogen, alkyl, heteroalkyl, aryl, or aralkyl; and
X is halo.
7. The article of claim 1 , wherein Z 1 is an azlactone group and the modifying agent is of formula HD-T, wherein D is oxy, thio, or —NR 3 —.
8. The article of claim 1 , wherein Z 1 is a glycidyl group and the modifying agent is of formula T-(CO)—OH or HD-T, wherein D is oxy, thio, or —NR 3 —.
9. A method of purifying or separating a target compound, wherein the method comprises providing an article comprising a modified grafted support of Formula (V)
SS-(CO)—NH—C(R 1 ) 2 —(CH 2 ) p —(CO)-Q-Y 1 -Q-(CO)—CR 2 U 4 —CH 2 —U 3 (V)
wherein
SS comprises a solid support;
p is an integer equal to 0 or 1;
each R 1 is each independently selected from alkyl, heteroalkyl, aryl, or aralkyl;
Y 1 is a first linking group comprising an alkylene, heteroalkylene, arylene, or combination thereof;
each Q is independently a divalent group selected from oxy, thio, or —NR 3 — where R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl;
each R 2 is independently hydrogen or an alkyl;
U 3 comprises at least one divalent monomeric unit of formula CR 2 (Y 2 L-T)-CH 2 —;
Y 2 is a second linking group selected from a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combination thereof;
U 3 includes at least one divalent monomeric unit of formula —CR 2 (Y 2 L-T)-CH 2 —;
U 4 is hydrogen or comprises at least one divalent monomeric unit of formula —CR 2 (Y 2 L-T)-CH 2 —;
L is an attachment group formed by reacting group Z 1 with a modifying group A of a modifying agent A-T;
Z 1 is a functional group selected from (1) an acidic group or a salt thereof, (2) an amino group or a salt thereof, (3) a hydroxyl group, (4) an azlactone group or a precursor of the azlactone group, (5) a glycidyl group, or (6) a combination thereof; and
T is a remainder of the modifying agent A-T and is equal to the modifying agent A-T minus the modifying group A; and
contacting the article with a sample containing the target compound, wherein the target compound interacts with or reacts with at least one group T of the modified grafted support.
10. The method of claim 9 , wherein the modified grafted support of Formula (V) is positioned within a chromatographic column or disposed on a surface of a filtration medium.
11. The method of claim 9 , wherein the target compound is a biomolecule.
12. A method of purifying or separating a target compound, wherein the method comprising providing an article comprising a grafted support of Formula (IV)
SS-(CO)—NH—C(R 1 ) 2 —(CH 2 ) p —(CO)-Q-Y 1 -Q-(CO)—CR 2 U 2 —CH 2 —U 1 (IV)
wherein
SS comprises a solid support;
p is an integer equal to 0 or 1;
each R 1 is each independently selected from alkyl, heteroalkyl, aryl, or aralkyl;
each Q is independently a divalent group selected from oxy, thio, or —NR 3 — where R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl;
Y 1 is a first linking group that comprises an alkylene, heteroalkylene, arylene, or combination thereof;
each R 2 is independently hydrogen or an alkyl;
U 1 comprises at least one divalent monomeric unit of formula —CR 2 (Y 2 Z 1 )—CH 2 —;
U 2 is hydrogen or comprises at least one divalent monomeric unit of formula —CR 2 (Y 2 Z 1 )—CH 2 —;
Y 2 is a second linking group selected from a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combination thereof; and
Z 1 is a functional group selected from (1) an acidic group or a salt thereof, (2) an amino group or a salt thereof, (3) a hydroxyl group, (4) an azlactone group or a precursor of the azlactone group, (5) a glycidyl group, or (6) a combination thereof; and
contacting the article with a sample containing the target compound, wherein the target compound interacts with or reacts with at least one functional group Z 1 of the grafted support.
13. The method of claim 12 , wherein the modified grafted support of Formula (IV) is positioned within a chromatographic column or disposed on a surface of a filtration medium.
14. The method of claim 12 , wherein the target compound is a biomolecule.