NOVEL CALIXCROWN DERIVATIVES, THEIR PRODUCING METHOD, SELF-ASSEMBLED MONOMOLECULAR LAYERS PRODUCED BY THE METHOD, AND METHOD FOR FIXING PROTEIN MONOMOLECULAR LAYER USING THE SELF-ASSEMBLED MONOMOLECULAR LAYERS

摘要

PURPOSE: The calixcrown derivatives, their producing method, self-assembled monomolecular layers produced by the method, and a method for fixing protein monomolecular layer using the self-assembled monomolecular layers are provided, thereby the calixcrown self-assembled monomolecular layers can be easily produced. CONSTITUTION: The calix(4)arene-biscrown-4 derivatives are represented by formula (1), in which R1, R2, R3, and R4 are independently -CH2SH, or two of R1 to R4 may combines together to forms -CH2-S-S-CH2-. The calix(4)arene-crown-5 derivatives are represented by formula (2), in which n is 1; R1, R2, R3 and R4 are independently -CH2SH or R1 and R3 are individually -CH2SH and R2 and R4 are individually H; R5 and R6 are independently -H, methyl, ethyl, propyl, isopropyl and isobutyl. The calix(4)arene-crown-6 derivatives are represented by formula (3), in which n is 2; R1, R2, R3 and R4 are independently -CH2SH or R1 and R3 are individually -CH2SH and R2 and R4 are individually H; R5 and R6 are independently -H, methyl, ethyl, propyl, isopropyl and isobutyl. The calixcrown derivatives are produced by chloromethylation reacting compounds of formula (2) or (3), wherein R1, R2, R3 and R4 are H and R5 and R6 are -CH3 or compounds of formula (1), wherein R1, R2, R3, R4 are H to change 2 or 4 groups of R1 to R4 into -CH2Cl; and changing C1 group into thiol(-SH) or two C1 groups into disulfide(S-S). The protein are fixed on self-assembled monomolecular layers by dipping gold substrate in a solution containing the calixcrown derivatives for 1 to 24 hours and dipping the self-assembled monomolecular layers in a solution containing proteins having molecular weight of 20,000 dalton or more for 1 to 2 hours.