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Cited by 40DNA and Nucleic Acid ChemistryMolecular spectroscopy and chiralityAdvanced NMR Techniques and Applications

A Proton Magnetic Resonance Study of the Ultraviolet Photoproduct of d(TpT) in Aqueous Solution

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Hruska, Frank E., Wood, Donald J., Ogilvie, Kelvin K., Charlton, James L.·1975·Canadian Journal of Chemistry
DOI 10.1139/v75-166
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Abstract

The p.m.r. data of d(TpT) and its predominant u.v. photoproduct d(T[p]T) in aqueous solution are compared. The data are consistent with the presence of a cis-syn cyclobutane ring in d(T[p]T). Consideration of the H 1′ chemical shifts leads to the conclusion that changes in the sugar–base torsion angle of both nucleotide fragments of the parent molecule are required to bring the thymine bases into alignment for photodimerization. The coupling constants indicate that the conformation of the 5′-terminal fragment is only slightly affected by the cyclobutane ring formation. Photodimerization brings about a distortion of the sugar pucker in the 3′-terminal fragment. In this fragment both the gauche-gauche and gauche-trans conformers are significantly populated whereas the trans-gauche form is excluded.

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  • NMR and X-ray studies of cis-syn CPD with S-cyanoethyl phosphotriester show the two pyrimidine bases rotated by −29° base twist, compared with the right-handed 36° value in B-form DNA.

    “NMR and X-ray diffraction studies of the ultraviolet photoproduct, cis-syn CPD, with the S-cyanoethyl phosphotriester have revealed that the two pyrimidine bases are rotated by −29° base twist, contrasting to the right-handed 36° value observed in B-form DNA [78, 79].”

    From Molecular Mechanisms of Ultraviolet Radiation‐Induced DNA Damage and Repair (2010) · cites this paper as [78]

    The Geometry of the Cyclobutane Ring section describes an NMR study of the cis-syn d(TpT) photoproduct, but says its data cannot independently assign the intact molecule’s ring configuration. The Sugar-Base Torsion Angles section reports reorientation after photodimerization; neither section gives a −29° base twist, a 36° B-DNA comparison, or an X-ray result for an S-cyanoethyl phosphotriester. Our copy supplies only part of what the sentence attributes to this source (page numbers unavailable). (LLM, conf=0.88)

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Research works printed but not linked: 31

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Authors
Hruska, F. E., Wood, D. J., Ogilvie, K. K., & Charlton, J. L.
Affiliations
University of Manitoba (CA)
ORCID
Wood, Donald J.
Venue
Canadian Journal of Chemistry
Publisher
Canadian Science Publishing
Published
1975-04-15
Volume
53
Issue
8
Pages
1193-1203
ISSN
  • 0008-4042 (ISSN-L)
  • 1480-3291
DOI
10.1139/v75-166
OpenAlex
W2022850048
Cited by
40
References
3
Citations by year
2024: 1 · 2012: 1
FWCI
0.39
Type
journal article
Language
en
Open access
Licence
www.nrcresearchpress.com/page/about/CorporateTextAndDataMining (tdm)
Locations
Canadian Journal of Chemistry (publishedVersion)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
  • Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
  • Physical Sciences › Chemistry › Spectroscopy › Advanced NMR Techniques and Applications
Keywords
cyclobutane pyrimidine dimers, photodimerization, sugar pucker, gauche-gauche conformation, aqueous solutions, 1H NMR chemical shifts, coupling constants

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