Porous base matrix having formyl group, adsorbent using the porous base matrix, method for production of the porous base matrix, and method for production of the adsorbent
View Patent ↗The present invention relates to a porous base matrix having formyl group, which base matrix has a structure represented by the formula (2) as a spacer, which structure is obtained by cleaving a group represented by the formula (1): wherein, R 1 represents a group forming a five-membered ring or a six-membered ring with —CH(OH)—CH(OH)—; a method for producing the porous base matrix; and an adsorbent obtained by binding a ligand on the porous base matrix. By the present invention, a high-intensity base matrix for an adsorbent and an adsorbent are provided. The amount of a ligand leaked from the adsorbend is small.
1. A method for producing a porous base matrix having a formyl group, comprising steps of
allowing a halohydrin or a bis- or higher-functional epoxy compound to act on a raw material porous base matrix in order to introduce an epoxy group to the raw material porous base matrix,
transforming the epoxy group into a glyceryl group,
allowing a periodate salt to act on the glyceryl group in order to transform the glyceryl group into a monoformyl group,
allowing a five-membered ring sugar containing at least an amino group or a six-membered ring sugar containing at least an amino group to react with the epoxy group and the monoformyl group in order to introduce a group represented by the general formula (1):
wherein, R 1 represents a group forming the sugar with —CH(OH)—CH(OH)—,
transforming the group (1) with a periodate salt into a group represented by the general formula (2):
wherein, R 1 is the same as the above.
2. The method for production according to claim 1 , wherein the porous base matrix precursor has 5 μmol or more of the group represented by the general formula (1) per 1 mL of the porous base matrix precursor.
3. The method for production according to claim 1 , wherein the group represented by the general formula (2) is derived by reacting a periodate with the group represented by the general formula (1).
4. An adsorbent, wherein an affinity ligand is bound on a porous base matrix having a formyl group,
wherein the porous base matrix is produced by steps of:
allowing a halohydrin or a bis- or higher-functional epoxy compound to act on a raw material porous base matrix in order to introduce an epoxy group to the raw material porous base matrix,
transforming the epoxy group into a glyceryl group,
allowing a periodate salt to act on the glyceryl group in order to transform the glyceryl group into a monoformyl group,
allowing a five-membered ring sugar containing at least an amino group or a six-membered ring sugar containing at least an amino group to react with the epoxy group and the monoformyl group in order to introduce a group represented by the general formula (1):
wherein, R 1 represents a group forming the sugar containing at least the amino group with —CH(OH)—CH(OH)—,
transforming the group (1) with a periodate salt into a group represented by the general formula (2):
wherein R 1 is the same as above, and
wherein the porous base matrix has the above group represented by the general formula (2) for a spacer.
5. The adsorbent according to claim 4 , wherein the amount of the affinity ligand is 1 mg or more and 1000 mg or less per 1 mL of the porous base matrix.
6. The adsorbent according to claim 4 ,
having a group represented by the general formula (3) or (4):
wherein, R 1 represents a group forming a six-membered ring sugar containing at least an amino group or a seven-membered ring sugar containing at least an amino group with the nitrogen atom.
7. The adsorbent according to claim 4 , wherein the affinity ligand is protein A.
8. The adsorbent according to claim 4 , wherein the concentration of the ligand leaked into an object from the adsorbent is 100 ppm or less.
9. The adsorbent according to claim 4 , wherein the absorbed amount of the object to be purified is 1 mg or more per 1 mL of the adsorbent.
10. A method for producing an adsorbent, comprising a step of binding an affinity ligand on a porous base matrix having a formyl group,
wherein the porous base matrix is produced by steps of:
allowing a halohydrin or a bis- or higher-functional epoxy compound to act on a raw material porous base matrix in order to introduce an epoxy group to the raw material porous base matrix,
transforming the epoxy group into a glyceryl group,
allowing a periodate salt to act on the glyceryl group in order to transform the glyceryl group into a monoformyl group,
allowing a five-membered ring sugar containing at least an amino group or a six-membered ring sugar containing at least an amino group to react with the epoxy group and the monoformyl group in order to introduce a group represented by the general formula (1):
wherein, R 1 represents a group forming the sugar containing at least the amino group with —CH(OH)—CH(OH)—,
transforming the group (1) with a periodate salt into a group represented by the general formula (2):
wherein R 1 is the same as above, and
wherein the porous base matrix has the above group represented by the general formula (2) for a spacer.
11. A method for purifying an immunoglobulin, comprising a step of using the adsorbent according to claim 7 .