Rajeev, Kallanthottathil G. ; Sanjayan, Gangadhar J. ; Ganesh, Krishna N. (1997) Conformationally restrained chiral analogues of spermine: chemical synthesis and improvements in DNA triplex stability Journal of Organic Chemistry, 62 (15). pp. 5169-5173. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo970414j
Related URL: http://dx.doi.org/10.1021/jo970414j
Abstract
The synthesis of novel chiral analogues of spermine, 11 (2R,4S) and 14 (2S,4R), is reported starting from trans-4-hydroxy-l-proline 3. These cyclic analogues are generated from linear, achiral spermine by incorporating a pyrrolidine ring on the backbone to effect conformational rigidity, with simultaneous creation of two asymmetric centers. The chiral analogues bind both AT and CG rich DNA duplexes as effectively as spermine and exhibit even better association with DNA triplex than spermine. The newer analogues have features for structural elaboration to novel molecular entities of potential importance in therapeutics and material design.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 10790 |
| Deposited On: | 09 Nov 2010 04:54 |
| Last Modified: | 31 May 2011 09:51 |
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