Conformationally-preorganized, MiniPEG-containing gamma-peptide nucleic acids
AssigneeCarnegie Mellon University
InventorsDanith H. Ly, Srinivas Rapireddy, Bichismita Sahu
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Abstract
The present invention relates to γ-PNA monomers according to Formula I where substituent groups R1, R2, R3, R4, R5, R6, B and P are defined as set forth in the specification. The invention also provides methodology for synthesizing compounds according to Formula I and methodology for synthesizing PNA oligomers that incorporate one or more Formula I monomers.
Claims21
A PNA oligomer of at least two monomer subunits in length that comprises an amine terminus and a carboxy terminus and that comprises at least one gamma PNA monomer subunit, wherein said gamma PNA monomer subunit has the formula XII;
- wherein,
- X is selected from the group consisting of adenine, cytosine, guanine, thymine, uracil, modified nucleobases, fluorophores and aromatic ligands;
- Y comprises the amine terminus of the PNA oligomer and optionally one or more additional linked PNA monomer subunits;
- Z comprises the carboxy terminus of the PNA oligomer and optionally one or more additional linked PNA monomer subunits,
- provided that at least one of Y or Z comprises at least one additional PNA monomer subunit;
- each of R1 and R2 is independently selected from the group consisting of hydrogen (H), linear or branched (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)hydroxylalkyl, (C3-C8)aryl, (C3-C8)cycloalkyl, C3-Cs)aryl(C1-C6)alkylene, (C3-C8)cycloalkyl(C1-C6)alkylene,
- provided that at least one of R1 and R2 is selected from the group consisting of
- each of R3 and R4 is independently selected from the group consisting of hydrogen (H),
- R5 is selected from the group consisting of hydrogen (H), linear or branched (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)hydroxylalkyl, (C3-C8)aryl, (C3-C8)cycloalkyl, (C3-C8)aryl(C1-C6)alkylene and (C3-C8)cycloalkyl(C1-C6)alkylene;
- P2 is selected from the group consisting of hydrogen (H), linear or branched (C1-C8)alkyl, 9-fluorenylmethyloxycarbonyl (Fmoc), t-butyloxycarbonyl (Boc), benzyloxycarbonyl (Cbz), benzyl (Bn), tosylate (Tos), allyloxycarbonyl (alloc), trityl (Trt), monomethoxytrityl (MMT) and dimethoxytrityl (DMT);
- P3 selected from the group consisting of hydrogen (H), linear or branched (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C8)aryl, (C3-C8)cycloalkyl, (C3-C8)aryl(C1-C6)alkylene and (C3-C8)cycloalkyl(C1-C6)alkylene;
- n is an integer from 1 to 10, inclusive;
- x is an integer from 1 to 10, inclusive;
- and
- y is an integer from 1 to 9, inclusive.
A PNA oligomer of at least two monomer subunits in length that comprises an amine terminus and a carboxy terminus and that comprises at least one gamma PNA monomer subunit, wherein said gamma PNA monomer subunit has the formula XXIII;
- wherein
- X is selected from the group consisting of adenine, cytosine, guanine, thymine, uracil, modified nucleobases, fluorophores and aromatic ligands;
- Y comprises the amine terminus of the PNA oligomer and optionally one or more additional linked PNA monomer subunits;
- Z comprises the carboxy terminus of the PNA oligomer and optionally one or more additional linked PNA monomer subunits,
- n is 1,
- x is an integer from 1 to 10, inclusive and
- R8 is selected from the group consisting of hydrogen (H), methyl, ethyl, and t-butyl, provided that at least one of Y or Z comprises at least one additional PNA monomer subunit.
A PNA oligomer of at least two monomer subunits in length that comprises an amine terminus and a carboxy terminus and that comprises at least one gamma PNA monomer subunit, wherein said gamma PNA monomer subunit has the formula XXIV;
- wherein
- X is selected from the group consisting of adenine, cytosine, guanine, thymine, uracil, modified nucleobases, fluorophores and aromatic ligands;
- Y comprises the amine terminus of the PNA oligomer and optionally one or more additional linked PNA monomer subunits;
- Z comprises the carboxy terminus of the PNA oligomer and optionally one or more additional linked PNA monomer subunits,
- n is 1,
- x is an integer from 1 to 10, inclusive, and
- R8 is selected from the group consisting of hydrogen (H), methyl, ethyl, and t-butyl, provided that at least one of Y or Z comprises at least one additional PNA monomer subunit.
Dependencies are inferred from the claim text.