Novel Functional Peptide Nucleic Acid Monomer and Process for Producing the Same

Abstract

A compound represented by general formula (I) below; (in the formula, A denotes B denotes R denotes H, NO 2 , NH 2 , NHCbz, Br, F, Cl or SO 3 Na 2 , and n is an integer of 1 to 4 ), and a process for producing the above compound characterised in that it includes a reaction between an activated ester and a t-butoxycarbonylaminoethylamine or an ω-amino acid derivative.

1 - 48 . (canceled) 
   
   
       49 . A process for producing a functional PNA monomer by reacting a t-butoxycarbonylaminoethylamine with a derivative of a functional molecule so as to incorporate the functional molecule into a PNA monomer, characterised in that the derivative of a functional molecule is an activated ester, wherein activated ester is characterised to have, on the carbonyl carbon forming the ester bond, a group represented by general formula (II) below, 
     
       
         
         
             
             
         
       
     
     (In the formula, A denotes 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       R denotes H, NO 2 , NH 2 , NHCbz, Br, F, Cl or SO 3 Na 2 , and n is an integer of 1 to 4.), 
       and, is characterised to have, on its carbonyl carbon, a pentafluorophenoxy group or a succinimidoxy group. 
     
   
   
       50 . A process for producing the activated ester according to  claim 49 , characterised in that it comprises reacting a carboxylic acid derivative of a functional molecule with a compound having a pentafluorophenoxy group or a succinimidoxy group. 
   
   
       51 . A process for producing the carboxylic acid derivative of a functional molecule according to  claim 52 , characterised in that it comprises reacting a derivative of the functional molecule with an aliphatic carboxylic acid. 
   
   
       52 . A process for producing a functional PNA monomer by reacting a derivative of a functional molecule, including following chemical formula (IV) at the terminal of molecule, with an ω-amino acid derivative represented by general formula (III) below, thereby incorporating the functional molecule into a PNA monomer, characterised in that the derivative of the functional molecule is an activated ester: 
     
       
         
         
             
             
         
       
     
     (In the formula, R 1  denotes a hydrogen atom or a straight- or branched-chain C 1  to C 5  alkyl group, and m denotes an integer of 1 to 11.), 
     
       
         
         
             
             
         
       
     
   
   
       53 . The production process according to  claim 52 , characterised in that the activated ester has, on its carbonyl group forming an ester bond, a group represented by general formula (II) below, either directly or via an aliphatic chain or a peptide chain: 
     
       
         
         
             
             
         
       
     
     (In the formula, A denotes 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       R denotes H, NO 2 , NH 2 , NHCbz, Br, F, Cl or SO 3 Na 2 , and n is n integer of 1 to 4.). 
     
   
   
       54 . The production process according to  claim 52 , characterised in that the activated ester has, on its carbonyl carbon, a pentafluorophenoxy group or a succinimidoxy group. 
   
   
       55 . The production process according to  claim 53 , characterised in that the activated ester has, on its carbonyl carbon, a pentafluorophenoxy group or a succinimidoxy group.