1ntt

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{{STRUCTURE_1ntt| PDB=1ntt | SCENE= }}
{{STRUCTURE_1ntt| PDB=1ntt | SCENE= }}
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'''5'(dCPCPUPCPCPUPUP)3':(rAGGAGGAAA)5', where P=propynyl'''
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===5'(dCPCPUPCPCPUPUP)3':(rAGGAGGAAA)5', where P=propynyl===
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==Overview==
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The 1-propynylation at C5 of consecutive pyrimidines in DNA can enhance DNA:RNA hybrid stability at 37 degrees C by over 1 kcal/mol of substitution [Barnes, T. W., III; Turner, D. H. J. Am. Chem. Soc.2001, 123, 4107-4118]. To provide information on the structural consequences of propynylation, two-dimensional NMR spectroscopy was used to study the structures of several oligonucleotides. Intraresidue nuclear Overhauser effect spectroscopy cross peaks were observed at 30 degrees C and a 200 ms mixing time in the H6-H1' region for 5'(dC(P)C(P)U(P)C(P)C(P)U(P)U(P)) (ssPrODN) but not for 5'(dCCUCCUU) (ssODN), suggesting preorganization of the propynylated single strand. NMR structures of the duplexes 5'(dC(P)C(P)U(P)C(P)C(P)U(P)U(P))3':3'(rGAGGAGGAAAU)5' (PrODN:RNA), 5'(dCC(P)U(P)C(P)C(P)U(P)U(P))3':3'(rGAGGAGGAAAU)5' (sPrODN1:RNA), and 5'(dCCUCCUU)3':3'(rGAGGAGGAAAU)5' (ODN:RNA) indicate that their global structures are almost identical. The NMR data, however, suggest that the 5'-end of sPrODN1:RNA is more dynamic than that of PrODN:RNA. In the propynylated duplexes, the propyne group stacks on the aromatic ring of the 5'-base and extends into the major groove. The results suggest that the increased stability of the propynylated duplexes is caused by preorganization of the propynylated single strand and different interactions in the double strand. The propynyl group provides volume exclusion, enhanced stacking, and possibly different solvation.
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{{ABSTRACT_PUBMED_12785839}}
==About this Structure==
==About this Structure==
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Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1NTT OCA].
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Full experimental information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1NTT OCA].
==Reference==
==Reference==
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[[Category: Propynyl]]
[[Category: Propynyl]]
[[Category: Rna]]
[[Category: Rna]]
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Tue Jul 29 13:47:26 2008''

Revision as of 10:47, 29 July 2008

Image:1ntt.png

Template:STRUCTURE 1ntt

5'(dCPCPUPCPCPUPUP)3':(rAGGAGGAAA)5', where P=propynyl

Template:ABSTRACT PUBMED 12785839

About this Structure

Full experimental information is available from OCA.

Reference

NMR studies of DNA single strands and DNA:RNA hybrids with and without 1-propynylation at C5 of oligopyrimidines., Znosko BM, Barnes TW 3rd, Krugh TR, Turner DH, J Am Chem Soc. 2003 May 21;125(20):6090-7. PMID:12785839

Page seeded by OCA on Tue Jul 29 13:47:26 2008

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