An NMR and conformational investigation of thetrans-syn cyclobutane photodimers of dUpdT

Tabaczynski, Walter A.; Lemaire, Danielle G. E.; Ruzsicska, B�la P.; Alderfer, James L.

doi:10.1002/(sici)1097-0282(199908)50:2<185::aid-bip7>3.0.co;2-n

Cited by 3 publications

(2 citation statements)

References 29 publications

(54 reference statements)

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“…For 3a , the magnitude of the H5‐H6′ interpyrimidine coupling constant J 5,6′ is 7.3 Hz. Using the Haasnoot‐de Leeuw‐Altona modified Karplus‐type equation (30,31) (MestRe‐J software (32)), such value corresponds to torsion angles [H C 5‐C C 5‐C C 6′‐H C 6′] of +32° or −35°. For 3c , the interpyrimidine coupling constant J 5,6′ amounts 7.9 Hz and means torsion angles [H C 5‐C C 5‐C C 6′‐H C 6′] of +31° or −28°.…”

Section: Resultsmentioning

confidence: 99%

“…The large J 5,6 * (7.3 Hz) and small J 5 *, 6 (3.2 Hz) interpyrimidine coupling constant are in favor of puckering A where H C 5H C 6* are a′‐a′ and H C 5*H C 6 are e′‐e′. The torsional angles [H C 5‐C C 5‐C C 6*‐H C 6*] and [H C 5*‐C C 5*‐C C 6‐H C 6] were calculated using a Karplus‐type equation (30,31) (MestRe‐J software (32)), to be +140.1° and −118.5°, respectively. Identifying H C 6* as pseudoaxial allowed to assign the nucleoside residue of 3b , initially arbitrarily labeled by a *, as the C C 5 ( S ) part represented Fig.…”

Section: Resultsmentioning

confidence: 99%

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Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside^†

Peyrane

Denhez

Guillaume

et al. 2021

Photochem & Photobiology

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The [2 + 2] photocycloaddition of natural pyrimidine nucleobases is devoid of regioselectivity. Although modified pyrimidines have been developed to selectively obtain syncyclobutane isomers, the targeted formation of anticyclobutane isomers has not been addressed yet. Herein, using NMR analyses and DFT calculations, we demonstrate that the acetone photosensitized excitation of the 4tetrazolouracil motif in the nucleoside series specifically provides anti-cyclobutane photoproducts in 51% yield. In addition, the cis stereomer formation is preferred over the transcyclobutane formation (71:29).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside^†

Peyrane

Denhez

Guillaume

et al. 2021

Photochem & Photobiology

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RNA Is More UV Resistant than DNA: The Formation of UV‐Induced DNA Lesions is Strongly Sequence and Conformation Dependent

Kundu

Linne

Marahiel

et al. 2004

Chemistry A European J

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DNA and RNA hairpins, which represent well-folded oligonucleotide structures, were irradiated and the amount of damaged hairpins was directly quantified by using ion-exchange HPLC. The types of photoproducts formed in the hairpins were determined by ESI-HPLC-MS/MS experiments. Irradiation of hairpins with systematically varied sequences and conformations (A versus B) revealed remarkable differences regarding the amount of photolesions formed. UV-damage formation is, therefore, a strongly sequence and conformation dependent process.

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Sensitized photochemistry of di(4-tetrazolouracil) dinucleoside monophosphate as a route to dicytosine cyclobutane photoproduct precursors

Peyrane

Clivio

2013

Photochem Photobiol Sci

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The DNA cis-syn cyclobutane photoproduct formed between two adjacent cytosine residues is highly mutagenic and responsible for the tandem CC to TT transition. However, its instability has prevented its in vitro study, so far. With a view to prepare oligodeoxynucleotides containing the CC cyclobutane lesion, we have synthesized in good yield a ditetrazolouracil cyclobutane dinucleotide photoproduct as a stable precursor of this photoproduct. Our approach also overcomes the low photochemical reactivity of the cytosine-cytosine deoxydinucleoside monophosphate.

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An NMR and conformational investigation of thetrans-syn cyclobutane photodimers of dUpdT

Cited by 3 publications

References 29 publications

Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside^†

Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside^†

RNA Is More UV Resistant than DNA: The Formation of UV‐Induced DNA Lesions is Strongly Sequence and Conformation Dependent

Sensitized photochemistry of di(4-tetrazolouracil) dinucleoside monophosphate as a route to dicytosine cyclobutane photoproduct precursors

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An NMR and conformational investigation of thetrans-syn cyclobutane photodimers of dUpdT

Cited by 3 publications

References 29 publications

Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside†

Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside†

RNA Is More UV Resistant than DNA: The Formation of UV‐Induced DNA Lesions is Strongly Sequence and Conformation Dependent

Sensitized photochemistry of di(4-tetrazolouracil) dinucleoside monophosphate as a route to dicytosine cyclobutane photoproduct precursors

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Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside^†

Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside^†