SYNTHESIS AND BINDING AFFINITY OF A CHIRAL PNA ANALOGUE

REFERENCES

• Ray , A. and Norden , B. 2000 . Peptide Nucleic Acid (PNA): Its Medical and Biotechnical Applications and Promise for the Future . FASEB J. , 14 ( 9 ) : 1041 – 1060 .
   Google Scholar
• Nielsen , P. E. , Egholm , M. , Berg , R. H. and Buchardt , O. 1991 . Sequence-Selective Recognition of DNA by Strand Displacement with a Thymine-Substituted Polyamide . Science , 254 ( 5037 ) : 1497 – 1500 .
   Google Scholar
• Demidov , V. , Potaman , V. N. , Frank-Kamenetskii , M. D. , Egholm , M. , Buchardt , O. , Sonnichsen , S. H. and Nielsen , P. E. 1994 . Stability of Peptide Nucleic Acids in Human Serum and Cellular Extracts . Biochem. Pharmacol. , 48 ( 6 ) : 1310 – 1313 .
   Google Scholar
• Schwarz , F. P. , Robinson , S. and Butler , J. M. 1999 . Thermodynamic Comparison of PNA/DNA and DNA/DNA Hybridization Reactions at Ambient Temperature . Nucleic Acids Res. , 27 ( 24 ) : 4792 – 4800 .
   Google Scholar
• Dueholm , K. L. , Egholm , M. , Behren , C. , Christensen , L. , Hansen , H. F. , Vulpius , T. , Petersen , K. H. , Berg , R. H. , Nielsen , P. E. and Buchardt , O. 1994 . Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization . J. Org. Chem. , 59 : 5767 – 5773 .
   Google Scholar
• Pooga , M. , Soomet , U. , Hallbrink , M. , Valkna , A. , Saar , K. , Rezaei , K. , Kahl , U. , Hao , J. X. , Xu , X. J. , Wisenfeld-Hallin , Z. , Hokfelt , T. , Bartfai , T. and Langel , U. 1998 . Cell Penetrating PNA Constructs Regulate Galanin Receptor Levels and Modify Pain Transmission in Vivo . Nat. Biotechnol. , 16 ( 9 ) : 857 – 860 .
   Google Scholar
• Larsen , H. J. , Bentin , T. and Nielsen , P. E. 1999 . Antisense Properties of Peptide Nucleic Acid. Biochim . Biophys. Acta. , 1489 ( 1 ) : 159 – 166 .
   Google Scholar
• Chandler , D. P. , Stults , J. R. , Anderson , K. K. , Cebula , S. , Schuck , B. L. and Brockman , F. J. 2000 . Affinity Capture and Recovery of DNA at Femtomolar Concentrations with Peptide Nucleic Acid Probes . Anal Biochem. , 283 ( 2 ) : 241 – 249 .
   Google Scholar
• Prescott , A. M. and Fricker , C. R. 1999 . Use of PNA Oligonucleotides for the in situ Detection of Escherichia Coli in Water . Mol Cell Probes , 13 ( 4 ) : 261 – 268 .
   Google Scholar
• Nilsson , P. , O'meara , D. , Edebratt , F. , Persson , B. , Uhlen , M. , Lundeberg , J. and Nygren , P. 1999 . Quantitative Investigation of the Modular Primer Effect for DNA and Peptide Nucleic Acid Hexamers . Anal. Biochem. , 269 ( 1 ) : 155 – 161 .
   Google Scholar
• Nielsen , P. E. , Egholm , M. and Buchardt , O. 1994 . Peptide Nucleic Acid (PNA): A DNA Mimic with a Peptide Backbone . Bioconj. Chem. , 5 ( 1 ) : 3 – 7 .
   Google Scholar
• Peffer , N. J. , Hanvey , J. C. , BiSi , J. E. , Thomson , S. A. , Hassman , C. F. , Nobel , S. A. and Babiss , L. E. 1993 . Strand-Invasion of Duplex DNA by Peptide Nucleic Acid Oligomers . Proc. Natl. Acad. Sci. USA , 90 ( 22 ) : 10648 – 10652 .
   Google Scholar
• D'Coster , M. , Kumar , V. A. and Ganesh , K. N. 1999 . Aminoethylprolyl Peptide Nucleic Acids(aepPNA): Chiral PNA Analogues that Form Highly Stable DNA:aepPNA2 Triplexes . Org. Lett. , 1 : 1513 – 1516 .
   Google Scholar
• Beylin , V. G. and Goel , O. P. 1987 . A Convenient Synthesis of t-Butyl N-(2-Bromoethyl) Carbamate . Org. Prep. Proced. Int. , 19 : 78 – 80 .
   Google Scholar
• Borcherding , D. R. , Butler , B. T. , Linnik , M. D. , Mehdi , S. , Dudley , M. W. and Edwards , C. K. 1996 . Cis(1S,3R)-1-(9-Adenyl)-3-Hydroxy-Cyclopentane Inhibits the Respiratory Burst from Polymorphonuclear Leukocytes and has in vivo Efficacy in an Acute and Chronic Model of Inflammation . Nucleosides Nucleotides , 15 : 967 – 979 .
   Google Scholar
• Bolon , P. J. , Sells , T. B. , Nuesca , Z. M. , Purdy , D. F. and Nair , V. 1994 . Novel Isomeric Dideoxynucleosides as Potential Antiviral Agents . Tetrahedron , 50 ( 26 ) : 7747 – 7764 .
   Google Scholar
• Lewis , A. F. , Revankar , G. R. and Rando , R. F. 1995 . Synthesis and in Vitro Anti-human Cytomegal Virus Activity of Certain Alkenyl Substituted Cytosines and 5-Halocytosines . J. Heterocycl. Chem. , 32 ( 5 ) : 1513 – 1515 .
   Google Scholar
• Howarth , N. and Wakelin , L. P.G. 1997 . α-PNA: A Novel Peptide Nucleic Acid Analogue of DNA . J. Org. Chem. , 62 : 5441 – 5450 .
   Google Scholar
• Reddy , P. M. and Hanna , N. B. Methods and Reagents for Cleaving and Deprotecting Oligonucleotides . US Patent 5,348,868 . September 20, 1994 .
   Google Scholar
• The optical rotation of the recovered dipeptide is [α]20 = 16.79, (c = 0.1095, 1 M acetic acid) and the optical rotation of the controlled dipeptide is [α]20 = 16.81, (c = 0.0963, 1 M acetic acid) .
   Google Scholar
• Kjellberg , J. and Liljenberg , M. 1986 . Regioselective Alkylation of 6-(β-Methoxyethoxy) Guanine to Give the 9-Alkylguanine Derivative . Tetrahedron Lett. , 27 ( 7 ) : 877 – 880 .
   Google Scholar