PNA monomer and precursor

Details PNA monomer and precursor PNA monomer and precursor

2006-04-04

2006-04-04

Berch, Mark L. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen bonded directly to ring carbon of the purine ring...

C544S277000, C544S312000, C544S317000, C544S383000, C530S333000, C560S013000, C562S430000

Reexamination Certificate

active

07022851

ABSTRACT:
This application relates to monomers of the general formula (I) for the preparation of PNA (peptide nucleic acid) oligomers and provides method for the synthesis of both predefined sequence PNA oligomers and random sequence PNA oligomers:whereinR1, R2, R3, R4, R5 is independently H, halogen, C1–C4alkyl, nitro, nitrile, C1–C4alkoxy, halogenated C1–C4alkyl, or halogenated C1–C4alkoxy, wherein at least one of R1, R3, and R5 is nitro;R6 is H or protected or unprotected side chain of natural or unnatural α-amino acid; andB is a natural or unnatural nucleobase, wherein when said nucleobase has an exocyclic amino function, said function is protected by protecting group which is labile to acids but stable to weak to medium bases.

REFERENCES:
patent: 4204870 (1980-05-01), Chapman et al.
patent: 5294713 (1994-03-01), Sugihara et al.
patent: 5539083 (1996-07-01), Cook et al.
patent: 6063569 (2000-05-01), Gildea et al.
patent: 6133444 (2000-10-01), Coull et al.
patent: 6172226 (2001-01-01), Coull et al.
patent: 2003/0225252 (2003-12-01), Kim et al.
patent: 10045751 (1997-02-01), None
patent: WO 92/20702 (1992-11-01), None
patent: WO 00/02899 (2000-01-01), None
Jackie C. Bloomer, Bioorganic & Medicinal Chemistry Letters, vol. 11, Issue 14, Jul. 23, 2001, pp. 1925-1929.
Siaugue et al., “Regioselective synthesis of N-functionalized 12-membered azapyridinomacrocycles bearing trialylcarboxylic-”, Tetrahedron, 57: 4713-4718.
Akaji et al.,Tetrahedron Lett., 33(22):3177-3180(1992).
Betts et al.,Science, 270:1838-1841(1995).
Blankemeyer-Menge et al.,Tetrahedron Lett., 31(12):1701-1704(1990).
Breipohl et al.,Bioorg-Med. Chem. Lett., 6(6):665-670(1996).
Breipohl, et al.,Tetrahedron, 53(43):14671-14686(1997).
Carpino,J. Am. Chem. Soc., 115:4397-4398(1993).
Castro et al.,Tetrahedron Lett., 14:1219-1222(1975).
Christensen et al.,J. Pept. Sci., 3:175-183(1995).
Coste et al.,Tetrahedron Lett., 31(2):205-208(1990).
Coste et al.,Tetrahedron Lett., 31(5)669-672(1990).
Coste et al.,Tetrahedron Lett., 32(17):1967-1970(1991).
Dourtoglou et al.,Synthesis, 572-574(1984).
Dueholm et al.,J. Org. Chem., 59:5767-5773(1994).
Dueholm et al.,New J. Chem., 21:19-31(1997).
Egholm et al.,J. Am. Chem. Soc., 114:1895-1897(1992).
Egholm et al.,Nature, 365:566-568(1993).
Egholm et al.,J. Chem. Soc. Commun., 800-801(1993).
Ehrlich et al.,Tetrahedron Lett., 34(30):4781-4784(1993).
Englisch et al.,Angew. Chem. Int. Ed. Engl., 30(6):613-629(1991).
Finn et al.,Nucleic Acid Research, 24(17):3357-3363(1996).
Hyrup et al.,J. Am. Chem. Soc., 116:7964-7970(1994).
Kim et al.,J. Am. Chem. Soc., 115(15):6477-6481(1993).
Kirstgen et al.,J. Chem. Soc. Chem. Commun., 1870-1871(1987).
Knorr et al.,Tetrahedron Lett., 30(15):1927-1930(1989).
Knudsen et al.,Nucleic Acids Res., 24(3):494-500(1996).
Leijon et al.,Biochemistry, 33:9820-9825(1994).
Mesmaeker et al.,Curr. Opinion Struct. Biol., 5:343-355(1995).
Nielsen,Curr. Opin. Biotech., 12:16-20(2001).
Nielsen et al.,Science, 254:1497-1500(1991).
Orum et al.,BioTechniques, 19(3):472-480(1995).
Peyman et al.,Angew. Chem. Int. Ed. Engl., 35(22):2636-2638(1996).
Puschl et al.,Tetrahedron Lett., 39:4707-4710(1998).
Stetsenko et al.,Tetrahedron Lett. 37(20):3571-3574(1996).
Thomson et al.,Tetrahedron, 51(22):6179-6194(1995).
Tomac et al.,J. Am. Chem. Soc., 118:5544-5552(1996).
Uhlman et al.,Angew. Chem. Int. Ed. Engl., 35(22):2632-2635(1996).
Will et al.,Tetrahedron, 51(44):12069-12082(1995).
Wittung et al.,J. Am. Chem. Soc., 118:7049-7054(1996).
Russ et al.,J. Org. Chem., 41:149-151(1976).

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