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

L. S. Kan; D. M. Cheng; S. Chandrasegaran; P. Pramanik; P. S. Miller

doi:10.1080/07391102.1987.10507678

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

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

Bloomberg School of Public Health

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

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 language	English (US)
Pages (from-to)	785-796
Number of pages	12
Journal	Journal of Biomolecular Structure and Dynamics
Volume	4
Issue number	5
DOIs	https://doi.org/10.1080/07391102.1987.10507678
State	Published - Apr 1987

ASJC Scopus subject areas

Structural Biology
Molecular Biology

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10.1080/07391102.1987.10507678

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title = "Structural and conformational studies on deoxyguanosyl-3{\textquoteright}, 5{\textquoteright}-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{\textquoteright}-5{\textquoteright} deoxyadenosine and its diastereomeric ethyl phosphotriester analogs were studied by {\textquoteleft}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{\textquoteright}g{\textquoteright} (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 {\textquoteleft}H NMR nuclear Overhauser enhancement experiments.",

author = "Kan, {L. S.} and Cheng, {D. M.} and S. Chandrasegaran and P. Pramanik and Miller, {P. S.}",

note = "Funding Information: The authors wish to thank Professors Paul 0. P. Ts'o and Wtlma K Olson for comments on the manuscript, to Dr. D. Callahan and Mr. S.M. Pulford for their technical help and to ProfessorS. K Yang ofUSUHS for the generous use of his Jasco 500A CD spectrometer. The JHU-Baltimore NMR Biomedical Facility Center was established by NIH grant #GM27512. This work is supported by NIH GM34252.",

year = "1987",

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doi = "10.1080/07391102.1987.10507678",

language = "English (US)",

volume = "4",

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AU - Kan, L. S.

AU - Cheng, D. M.

AU - Chandrasegaran, S.

AU - Pramanik, P.

AU - Miller, P. S.

N1 - Funding Information: The authors wish to thank Professors Paul 0. P. Ts'o and Wtlma K Olson for comments on the manuscript, to Dr. D. Callahan and Mr. S.M. Pulford for their technical help and to ProfessorS. K Yang ofUSUHS for the generous use of his Jasco 500A CD spectrometer. The JHU-Baltimore NMR Biomedical Facility Center was established by NIH grant #GM27512. This work is supported by NIH GM34252.

PY - 1987/4

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

Abstract

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