Structural and conformational studies on deoxyguanosyl-3’, 5’-deoxyadenosine monophosphate and its ethyl phosphotriester analogs left-handed dimers1

L. S. Kan, D. M. Cheng, Srinivasan Chandrasegaran, P. Pramanik, P. S. Miller

Research output: Contribution to journalArticle

Abstract

The mode of base-base stacking, the handedness and the sugar(dGpA)phosphate backbone conformation of deoxyguanosyl 3’-5’ deoxyadenosine and its diastereomeric ethyl phosphotriester analogs were studied by ‘H NMR, UV and CD spectroscopy. The results indicate the three dimers are left-handed, while the sugar phosphate backbone is comprised predominantly of C2.-endo, gg (C4.-C5.) and g’g’ (C5.-0) conformers. The two bases are extensively stacked and interact about 90° along the dyad axes. The extent of base overlap in dGpA is slightly greater than in either ethyl phosphotriester analog. The absolute configurations of the two ethyl phosphotriester diastereoisomers of dGp A can be assigned by one-dimensional and two-dimensional ‘H NMR nuclear Overhauser enhancement experiments.

Original languageEnglish (US)
Pages (from-to)785-796
Number of pages12
JournalJournal of Biomolecular Structure and Dynamics
Volume4
Issue number5
DOIs
StatePublished - 1987

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Sugar Phosphates
Functional Laterality
Spectrum Analysis
5'-deoxyadenosine
cordycepin
deoxyguanylyl-(3'-5')-deoxyadenosine
2'-deoxy-5'-adenosine monophosphate

ASJC Scopus subject areas

  • Molecular Biology
  • Structural Biology

Cite this

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title = "Structural and conformational studies on deoxyguanosyl-3’, 5’-deoxyadenosine monophosphate and its ethyl phosphotriester analogs left-handed dimers1",
abstract = "The mode of base-base stacking, the handedness and the sugar(dGpA)phosphate backbone conformation of deoxyguanosyl 3’-5’ deoxyadenosine and its diastereomeric ethyl phosphotriester analogs were studied by ‘H NMR, UV and CD spectroscopy. The results indicate the three dimers are left-handed, while the sugar phosphate backbone is comprised predominantly of C2.-endo, gg (C4.-C5.) and g’g’ (C5.-0) conformers. The two bases are extensively stacked and interact about 90° along the dyad axes. The extent of base overlap in dGpA is slightly greater than in either ethyl phosphotriester analog. The absolute configurations of the two ethyl phosphotriester diastereoisomers of dGp A can be assigned by one-dimensional and two-dimensional ‘H NMR nuclear Overhauser enhancement experiments.",
author = "Kan, {L. S.} and Cheng, {D. M.} and Srinivasan Chandrasegaran and P. Pramanik and Miller, {P. S.}",
year = "1987",
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T1 - Structural and conformational studies on deoxyguanosyl-3’, 5’-deoxyadenosine monophosphate and its ethyl phosphotriester analogs left-handed dimers1

AU - Kan, L. S.

AU - Cheng, D. M.

AU - Chandrasegaran, Srinivasan

AU - Pramanik, P.

AU - Miller, P. S.

PY - 1987

Y1 - 1987

N2 - The mode of base-base stacking, the handedness and the sugar(dGpA)phosphate backbone conformation of deoxyguanosyl 3’-5’ deoxyadenosine and its diastereomeric ethyl phosphotriester analogs were studied by ‘H NMR, UV and CD spectroscopy. The results indicate the three dimers are left-handed, while the sugar phosphate backbone is comprised predominantly of C2.-endo, gg (C4.-C5.) and g’g’ (C5.-0) conformers. The two bases are extensively stacked and interact about 90° along the dyad axes. The extent of base overlap in dGpA is slightly greater than in either ethyl phosphotriester analog. The absolute configurations of the two ethyl phosphotriester diastereoisomers of dGp A can be assigned by one-dimensional and two-dimensional ‘H NMR nuclear Overhauser enhancement experiments.

AB - The mode of base-base stacking, the handedness and the sugar(dGpA)phosphate backbone conformation of deoxyguanosyl 3’-5’ deoxyadenosine and its diastereomeric ethyl phosphotriester analogs were studied by ‘H NMR, UV and CD spectroscopy. The results indicate the three dimers are left-handed, while the sugar phosphate backbone is comprised predominantly of C2.-endo, gg (C4.-C5.) and g’g’ (C5.-0) conformers. The two bases are extensively stacked and interact about 90° along the dyad axes. The extent of base overlap in dGpA is slightly greater than in either ethyl phosphotriester analog. The absolute configurations of the two ethyl phosphotriester diastereoisomers of dGp A can be assigned by one-dimensional and two-dimensional ‘H NMR nuclear Overhauser enhancement experiments.

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