Chemistry: molecular biology and microbiology – Carrier-bound or immobilized enzyme or microbial cell;... – Enzyme or microbial cell is immobilized on or in an organic...
Patent
1997-08-28
1999-02-02
O'Sullivan, Peter
Chemistry: molecular biology and microbiology
Carrier-bound or immobilized enzyme or microbial cell;...
Enzyme or microbial cell is immobilized on or in an organic...
435180, 435181, 436530, 436531, 436532, 436533, 436534, 530324, 530328, 530814, 530815, 530816, 536 30, 536 56, 536 92, C12N 1104, C12N 1106, C12N 1108, G01N 33544
Patent
active
058663878
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a method for immobilizing a ligand or a compound having a ligand bonded thereto onto a solvent-insoluble carrier having aldehyde groups.
BACKGROUND ART
Methods for immobilizing a ligand onto a carrier have been studied in large numbers for researches in an immobilized enzyme, and the like, and also industrially utilized for producing an adsorbent and the like. Representative examples of the methods are the following methods: activating method and successively reacting it with an amino group of a ligand, esterifing a carboxyl group on a carrier, converting the resulting ester into a hydrazide, successively converting the resulting hydrazide into an azide, and finally replacing the resulting azide group with an amino group of a ligand, diazonium salt on a carrier and making it react with an amino group of a ligand, condensing an amino group or carboxyl group on a carrier with a carboxyl group or amino group of a ligand with a condensing reagent, acetyl bromide group or 4,6-dichloro-s-triazinyl group onto a carrier and making it react with an amino group of a ligand, crosslinking an amino group on a carrier and an amino group of a ligand with glutaraldehyde and reducing the resulting compound, and the like (Atsuo Tanaka, Takuo Kawamoto, Gendai Kagaku, pp. 24-30, July 1992). A method for immobilizing a ligand onto a solvent-insoluble carrier having an aldehyde group is based on the method (6) mentioned above. And this method comprises reacting a ligand having an amino group to generate a Schiff base and successively reducing it (a reductive amination).
Outlines of the above-mentioned immobilizing methods (1)-(6) are shown by the following reaction formulas. In the following chemical reaction formulas, Z is a carrier and E is an enzyme. ##STR2##
However, these methods have the following defects. immobilization in a ligand, it is extremely difficult to immobilize the ligand with a functional group existing at a prescribed position of the ligand, because there are plural immobilization points. Furthermore, it is not preferable that there are many functional groups in a ligand, because the possibility that many bonds are formed at many points in the ligand becomes high. Also, in case the number of functional groups in the above-mentioned ligand is reduced in order to avoid forming bonds at multi-points, a reaction yield becomes low. The methods corresponding to these are the above-mentioned methods (1), (2), (3), (4), (5) and (6). The methods corresponding to these, are the above-mentioned methods (2), (3), (4) and (5).
In other words, these methods have considerable limits in immobilizing a ligand at a prescribed position thereof onto a solvent-insoluble carrier. Especially in case a peptide or protein is used as a ligand, it is impossible to immobilize a ligand with a prescribed amino group onto the carrier, because a peptide or protein often has amino groups in a side chain (in other words, there exist plural amino groups in one molecule).
On the other hand, it has been known as a reaction of organic synthesis chemistry for a long time that a thiazolidine structure is formed when an aldehyde compound and a derivative of aminoethanethiol (HSCH.sub.2 CH.sub.2 NH.sub.2) are reacted in the presence of an acidic or basic catalyst in an aqueous solution (Schmolka IR, J. Amer. Chem. Soc., 79, p.4716(1957). In late years, this classical reaction has been studied for applying it to bond formation between peptides, and it has been reported recently that peptides can be bonded each other efficiently by this reaction (C. F. Liu, J. P. Tam, Proc. Natl. Acad. Sci. USA, 91, p.6584(1994), C. Rao and J. P. Tam, J. Am. Chem. Soc.), 116, p.6975(1994)).
This method introduces an aldehyde group into the C-terminus of one of two kinds of peptides and has it react with the other peptide (N-terminal cysteine), and the reaction is performed in an aqueous solution wherein both reactants are dissolved in water. In other words, it can be said that such a reaction is known as a reaction
REFERENCES:
"Immobilization of Biocatalyst", Atsuo Tanaka et al., Gendai Kagaku pp. 24-30, Jul., 1992 (and translation-in-part thereof).
"Thiazolidine Chemistry. III. The Preparation and Reduction of Some 2-Phenyl-3-n-alkyl-4-thiazolidinones", Irving Schmolka et al., J. Am. Chem. Soc., vol. 79, pp. 4716-4720, Sep., 1957.
"Peptide segment ligation strategy without use of protecting groups", Chuan-Fa Liu et al., Proc. Natl. Acad. Sci. USA, vol. 91, No. 6584-6588, Jul., 1994.
"Synthesis of Peptide Dendrimer", Chang Rao et al., J. Am. Chem. Soc. vol. 116, No. 15 pp. 6975-6976, 1994.
Ogino Eiji
Suzuki Kazuo
Tani Nobutaka
Kanegafuchi Kagaku Kogyo & Kabushiki Kaisha
O'Sullivan Peter
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