Method for producing organic sulfur compound, carrier, method for producing said carrier, ligand-immobilizing carrier, chromatography column, and method for detecting or isolating target substance
A carrier which may have excellent pressure resistance, and even when a protein ligand is not immobilized thereon, a high dynamic binding capacity to a target substance, and a high performance of separating a target substance from a biological sample. Such a carrier may include a polymer having a crosslinked structure containing a divalent group of formula (1): wherein R 1 to R 4 are independently a single bond or divalent hydrocarbon group, R 5 and R 6 are independently H or a hydrocarbon group, X is a thio group, sulfinyl group, sulfonyl group, oxy group, >N(—R 31 ), >Si(—R 32 ) 2 , >P(—R 33 ), >P(═O)(—R 34 ), >B(—R 35 ), or >C(—R 36 ) 2 (R 31 to R 36 independently being H or hydrocarbon group), and * is a bond, provided that when both R 1 and R 3 or both R 2 and R 4 are a divalent hydrocarbon group, respectively, R 1 and R 3 or R 2 and R 4 may form a ring together with an adjacent carbon atom.
1. A method for producing a compound comprising a divalent group of formula (21)
Wherein R 51 and R 52 independently represent-being a divalent group derived from the ring opening of a cyclic ether group, X 2 being a thio group, a sulfinyl group, or a sulfonyl group, the method comprising:
reacting a cyclic ether group-containing compound with a thiocarboxylate in the presence of an aqueous solvent having a water content in a range of from 3 to 100% by mass, based on a total mass of the aqueous solvent.
2. The method of claim 1 , wherein the thiocarboxylate is of formula (13):
wherein
R 22 is H or a monovalent organic group, and
M is a cation which forms the thiocarboxylate.
3. The method of claim 1 , wherein the thiocarboxylate is a thioacetate.
4. A compound comprising a divalent group of formula (21), obtained by the method of claim 1 .
5. The method of claim 1 , wherein the water content of the aqueous solvent is in a range of from 20 to 100% by mass, based on the total mass of the aqueous solvent.
6. The method of claim 1 , wherein the aqueous solvent is present in the reacting in a range of from 10 to 2000 parts by mass, with respect to 100 parts by mass of the compound comprising the cyclic ether group.
7. The method of claim 1 , wherein the thiocarboxylate is present in the reacting in a range of from 0.01 to 5 mol., with respect to 1 mol. of the cyclic ether group.
8. The method of claim 1 , wherein the compound comprising the divalent group of formula (21) has a formula (B):
wherein
R 51 and R 52 are independently a divalent group formed by ring-opening of a cyclic ether group,
R 53 and R 54 are independently H or a methyl group,
R 55 and R 56 are independently a halogen atom or an organic group,
R 57 and R 58 are independently a single bond or a divalent linking group,
X 2 is a thio group, a sulfinyl group, or a sulfonyl group, and
n1 and n2 are independently an integer in a range of from 0 to 4.
9. The method of claim 8 , wherein, in the formula (B), R 53 and R 54 are a methyl group.