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US 2019/0292227 A1Published application
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.
Claims19
A peptide nucleic acid (PNA) monomer having the following formula:
- wherein
- B is adenine, guanine, cytosine, thymine, or uracil;
- P is selected from the group consisting of hydrogen (H), 9-fluorenylmethyloxycarbonyl (Fmoc),
- t-butyloxycarbonyl (Boc), benzyloxycarbonyl (Cbz), benzyl (Bn), tosylate (Tos), allyloxycarbonyl (alloc), benzhydryloxycarbonyl (Bhoc), trityl (Trt), monomethoxytrityl (MMT) and dimethoxytrityl (DMT);
- 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-C8)aryl(C1-C6)alkylene, (C3-C8)cycloalkyl(C1-C6)alkylene, and
- provided that at least one of R1 and R2 is
- each of R3 and R4 is independently selected from the group consisting of hydrogen (H) and
- 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;
- R6 is selected from the group consisting of hydrogen (H), linear or branched (C1-C8)alkyl, substituted or unsubstituted (C3-C8)aryl and (C3-C8)aryl(C1-C6)alkylene;
- P1 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);
- n is an integer from 0 to 10, inclusive;
- and
- q is an integer from 0 to 10, inclusive.
11 more elements
Dependencies are inferred from the claim text.