(2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: synthesis and duplex/triplex stability
作者： Pravin S. Shirude , Vaijayanti A. Kumar , Krishna N. Ganesh
DOI: 10.1016/J.TET.2004.07.080
关键词:
摘要: This article reports the design and facile synthesis of novel chiral six-membered PNA analogues (2S,5R/2R,5S)-1-(N-Boc-aminoethyl)-5-(thymin-1-yl)pipecolic acid, aepipPNA IV that upon incorporation into standard aegPNA sequences effected stabilization complexes with complementary target DNA. Substitution unit by designed monomer at C-terminus was more effective than substitution N-terminus. The stabilizing behaviour improved degree found to be dependent on their relative positions in sequence. piperidine ring may freeze rigid chair conformations stereochemistry substituents effect direct complex formation DNA/RNA sequence-specific nucleobase recognition. In present analogues, l-trans stereochemical disposition seems lead favorable pre-organization oligomers for results reported here further expand repertoire cyclic analogues.
elsevier.com
sci-hub.se 参考文章(27)
Michael J Gait, Oligonucleotide synthesis : a practical approach Published in <b>1984</b> in Oxford by IRL press. ,(1984)
Eugen Uhlmann, Anusch Peyman, Gerhard Breipohl, David W. Will, PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties Angewandte Chemie International Edition. ,vol. 37, pp. 2796- 2823 ,(1998) , 10.1002/(SICI)1521-3773(19981102)37:20<2796::AID-ANIE2796>3.0.CO;2-K
E. Kaiser, R.L. Colescott, C.D. Bossinger, P.I. Cook, Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides Analytical Biochemistry. ,vol. 34, pp. 595- 598 ,(1970) , 10.1016/0003-2697(70)90146-6
Ask Püschl, Thomas Boesen, Tullia Tedeschi, Otto Dahl, Peter E. Nielsen, Synthesis of (3R,6R)- and (3S,6R)-piperidinone PNA Journal of the Chemical Society, Perkin Transactions 1. pp. 2757- 2763 ,(2001) , 10.1039/B103901F
Michael Egholm, Ole Buchardt, Leif Christensen, Carsten Behrens, Susan M. Freier, David A. Driver, Rolf H. Berg, Seog K. Kim, Bengt Norden, Peter E. Nielsen, PNA hybridizes to complementary oligonucleotides obeying the Watson–Crick hydrogen-bonding rules Nature. ,vol. 365, pp. 566- 568 ,(1993) , 10.1038/365566A0
Patrick D Bailey, Justin S Bryans, Chiral synthesis of 5-hydroxy-(L)-pipecolic acids from (L)-glutamic acid Tetrahedron Letters. ,vol. 29, pp. 2231- 2234 ,(1988) , 10.1016/S0040-4039(00)86719-2
David R. Adams, Partrick D. Bailey, Ian D. Collier, John D. Heffernan, Stephen Stokes, An efficient route to the α-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid Chemical Communications. pp. 349- 350 ,(1996) , 10.1039/CC9960000349
Gregg B. Fields, Cynthia g. Fields, Solvation effects in solid-phase peptide synthesis Journal of the American Chemical Society. ,vol. 113, pp. 4202- 4207 ,(1991) , 10.1021/JA00011A023
Pravin S. Shirude, Vaijayanti A. Kumar, Krishna N. Ganesh, Chimeric peptide nucleic acids incorporating (2S,5R)-aminoethyl pipecolyl units: synthesis and DNA binding studies ☆ Tetrahedron Letters. ,vol. 45, pp. 3085- 3088 ,(2004) , 10.1016/J.TETLET.2004.02.099
D. A. Barawkar, K. G. Rajeev, V. A. Kumar, K. N. Ganesh, Triplex formation at physiological pH by 5-Me-dC-N4-(spermine) [X] oligodeoxynucleotides: non protonation of N3 in X of X*G:C triad and effect of base mismatch/ionic strength on triplex stabilities. Nucleic Acids Research. ,vol. 24, pp. 1229- 1237 ,(1996) , 10.1093/NAR/24.7.1229