Carbopeptoids and carbonucleotoids

Abstract

Libraries are synthesized with oligomeric carbopeptoids and carbonucleotoids. Carbopeptoids are oligosaccharides having carbohydrate subunits linked to one another by amide bonds. Carbonucleotoids are oligosaccharides having carbohydrate subunits linked to one another by phosphodiester bonds. Carbopeptoid libraries may be fabricated using automated polypeptide synthesizers. Carbonucleotoid libraries may be fabricated using automated polynucleotide synthesizers.

What is claimed is:  
     
         1 . An oligomeric carbopeptoid compound comprising carbohydrate amino acid subunits (CA's) coupled to one another via an amide linkage having a carbonyl carbon and an amido nitrogen represented by the following formula:  
       CA 1 —(CO—NH)—CA 2    wherein:    CA 1  is a first carbohydrate amino acid subunit having an anomeric carbon bonded to the carbonyl carbon of said amide linkage for forming a C-glycosidic linkage therewith and    CA 2  is a second carbohydrate amino acid subunit having a non-anomeric carbon bonded to the amido nitrogen of said amide linkage.    
     
     
         2 . In a process for synthesizing an oligomeric carbopeptoid compound, a coupling step wherein two or more carbohydrate amino acid subunits (CA's) are coupled by means of an amide linkage having a carbonyl carbon and an amido nitrogen for synthesizing said oligomeric carbopeptoid compound, said amide linkage being represented by a formula as follows:  
       CA 1 —(CO—NH)—CA 2    wherein:    CA 1  is a first carbohydrate amino acid subunit having an anomeric carbon bonded to the carbonyl carbon of said amide linkage for forming a C-glycosidic linkage therewith; and    CA 2  is a second carbohydrate amino acid subunit having a non-anomeric carbon bonded to the amido nitrogen of said amide linkage.    
     
     
         3 . A library of oligomeric carbopeptoid compounds employable for drug screening, each oligomeric carbopeptoid compound including at least two carbohydrate amino acid subunits (CA's) coupled to one another via an amide linkage having a carbonyl carbon and an amido nitrogen, said amide linkage being represented by the following formula:  
       CA 1 —(CO—NH)—CA 2    wherein:    CA 1  is a first carbohydrate amino acid subunit having an anomeric carbon bonded to the carbonyl carbon of said amide linkage for forming a C-glycosidic linkage therewith; and    CA 2  is a second carbohydrate amino acid subunit having a non-anomeric carbon bonded to the amido nitrogen of said amide linkage.    
     
     
         4 . An improved process for synthesizing a library of oligomers, the process employing an elongation step wherein subunits are coupled to one another to produce the oligomers, wherein the improvement comprises: 
 in said elongation step the oligomer includes at least two carbohydrate amino acid subunits (CA's) coupled to one another via an amide linkage having a carbonyl carbon and an amido nitrogen represented by the following formula:    CA 1 —(CO—NH)—CA 2      wherein:    CA 1  is a first carbohydrate amino acid subunit having an anomeric carbon bonded to the carbonyl carbon of said amide linkage for forming a C-glycosidic linkage therewith; and    CA 2  is a second carbohydrate amino acid subunit having a non-anomeric carbon bonded to the amido nitrogen of said amide linkage.    
     
     
         5 . A derived carbohydrate amino acid having an anomeric carbon and non-anomeric carbons, 
 said anomeric carbon being substituted with a carboxyl radical,    each of said non-anomeric carbons being substituted with a radical selected from the group consisting of blocked hydroxyl, blocked amino, differentially protected amino, and hydrogen, with the proviso that at least one radical is a differentially protected amino.    
     
     
         6 . A derived carbohydrate amino acid having an anomeric carbon and non-anomeric carbons, 
 said anomeric carbon being substituted with a carboxyl radical,    each of said non-anomeric carbons being substituted with a radical selected from the group consisting of blocked hydroxyl, blocked amino, unprotected amino, and hydrogen, with the proviso that at least one radical is an unprotected amino and at least one radical is a blocked hydroxyl or amino.    
     
     
         7 . An oligomeric carbonucleotoid molecule comprising carbohydrate C-glycoside subunits (CG's) coupled to one another via a phosphodiester linkage represented by the following structure:  
       CG 1 —C 1 —(O—PO(OH)—O)—CG 2    wherein:    (O—PO(OH)—O) is said phosphodiester linkage;    CG 1 —C 1 ′ is a first carbohydrate C-glycoside subunit having an anomeric carbon forming a C-glycosidic bond with a carbon C 1 ′, said carbon C 1 ′ being bonded to said phosphodiester linkage; and    CG 2  is a second carbohydrate C-glycoside subunit having a non-anomeric carbon bonded to said phosphodiester linkage.    
     
     
         8 . In a process for synthesizing an oligomeric carbonucleotoid molecule, a coupling step wherein two or more carbohydrate C-glycoside subunits (CG's) are coupled by means of a phosphodiester linkage, said phosphodiester linkage being represented by a formula as follows:  
       CG 1 —C 1 ′—(O—PO (OH)—O)—CG 2    wherein:    (O—PO(OH)—O) is said phosphodiester linkage;    CG 1 —C 1 ′ is a first carbohydrate C-glycoside subunit having an anomeric carbon forming a C-glycosidic bond with a carbon C 1 ′, said carbon C 1 ′ being bonded to said phosphodiester linkage; and    CG 2  is a second carbohydrate C-glycoside subunit having a non-anomeric carbon bonded to said phosphodiester linkage.    
     
     
         9 . A library of oligomeric carbonucleotoid molecules employable for drug screening, each oligomeric carbonucleotoid molecule including at least two carbohydrate 
 C-glycoside subunits (CG's) coupled to one another by means of a phosphodiester linkage, said phosphodiester linkage being represented by a formula as follows:    CG 1 —C 1 ′—(O—PO (OH)—O)—CG 2      wherein:    (O—PO(OH)—O) is said phosphodiester linkage;    CG 1 —C 1 ′ is a first carbohydrate C-glycoside subunit having an anomeric carbon forming a C-glycosidic bond with a carbon C 1 ′, said carbon C 1 ′ being bonded to said phosphodiester linkage; and    CG 2  is a second carbohydrate C-glycoside subunit having a non-anomeric carbon bonded to said phosphodiester linkage.    
     
     
         10 . An improved process for synthesizing a library of oligomers, the process employing an elongation step wherein subunits are coupled to one another to produce the oligomers, wherein the improvement comprises: 
 in said elongation step the oligomer is a carbonucleotoid including at least two carbohydrate C-glycoside subunits (CG's) are coupled by means of a phosphodiester linkage, said phosphodiester linkage being represented by a formula as follows:    CG 1 —C 1 ′—(O—PO (OH)—O)—CG 2      wherein:    (O—PO(OH)—O) is said phosphodiester linkage;    CG 1 —C 1 ′ is a first carbohydrate C-glycoside subunit having an anomeric carbon forming a C-glycosidic bond with a carbon C 1 ′, said carbon C 1 ′ being bonded to said phosphodiester linkage; and    CG 2  is a second carbohydrate C-glycoside subunit having a non-anomeric carbon bonded to said phosphodiester linkage.    
     
     
         11 . A derived carbohydrate C-glycoside having an anomeric carbon and non-anomeric carbons, 
 said anomeric carbon forming a C-glycosidic bond with a carbon C 1 ′, said carbon C 1 ′ being bonded to an activated phosphite,    each of said non-anomeric carbons being substituted with a radical selected from the group consisting of blocked hydroxyl, differentially protected hydroxyl, and hydrogen, with the proviso that at least one radical is a differentially protected hydroxyl.    
     
     
         12 . A derived carbohydrate C-glycoside having an anomeric carbon and non-anomeric carbons, 
 said anomeric carbon forming a C-glycosidic bond with a carbon C 1 ′, said carbon C 1 ′ being bonded to an activated phosphite,    each of said non-anomeric carbons being substituted with a radical selected from the group consisting of blocked hydroxyl, unprotected hydroxyl, and hydrogen, with the proviso that at least one radical is an unprotected hydroxyl and at least one radical is a blocked hydroxyl.