An Efficient Synthesis of a Furan-Side Furocoumarin Thymidine Monoadduct

Kobertz, William R.; Essigmann, John M.

doi:10.1021/jo9619084

Cited by 5 publications

(2 citation statements)

References 32 publications

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“…165,166 In order to study the mechanism of this anti-cancer drug in more detail and to create a compound that can site specifically induce DNA crosslinks for repair studies, Essigmann et al synthesized the thymidine-psoralene furan reaction product as the phosphoramidite building block 139 amenable to solid phase oligonucleotide synthesis (Scheme 18). 167,168 The starting point is the benzofuran derivative 140, which, after cleavage of the MOM-protection group with HCl to give 141, is cyclized with dimethylacetamide dimethyl acetal to furnish the psoralene ethyl ester 142. Saponification of the ethyl ester to 143 and esterification with thymidine 48 yielded the thymidine-psoralene conjugate 144.…”

Section: Building Blocks For Dna Crosslinks 162mentioning

confidence: 99%

Synthesis of DNA Lesions and DNA-Lesion-Containing Oligonucleotides for DNA-Repair Studies

Butenandt¹,

Burgdorf²,

Carell³

1999

Synthesis

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DNA and RNA are the molecules which store the genetic information in every organism. Both macromolecules are severely damaged by a variety of exogenous and endogenous events. This leads to a loss of genetic information. Main lesions are strand breaks, apurinic and apyrimidinic sites and a variety of DNA bases with an altered structure. The result of these DNA modifications are cell death, mutations and in the worst scenario carcinogenous growth. In order to study the effect of DNA lesions on the structure of the DNA double helix, a variety of lesion building blocks were recently synthesized and incorporated into oligonucleotides. In addition, oligonucleotides which contain DNA lesions at specific sites are the basis for a detailed investigation of repair mechanisms that were developed by organisms in order to counteract the lethal effect of DNA damage. This review article describes the recent synthetic progress that has enabled the preparation of DNA lesion phosphoramidite building blocks. The synthetic procedures employed for their preparation and the methods used to incorporate these building blocks into oligonucleotides are described. The biological effect of each particular lesion is briefly recapitulated.

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Section: Building Blocks For Dna Crosslinks 162mentioning

confidence: 99%

Synthesis of DNA Lesions and DNA-Lesion-Containing Oligonucleotides for DNA-Repair Studies

Butenandt¹,

Burgdorf²,

Carell³

1999

Synthesis

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show abstract

“…The synthesis of the suitably protected psoralen−thymidine phosphoramidite is shown in Scheme . The synthesis of deoxynucleoside 2 has been previously described . Protection of the 5‘ hydroxyl of 2 with 4,4-dimethoxytrityl chloride (DMT-Cl) in the presence of silver nitrate led to rapid conversion to 3 .…”

mentioning

confidence: 99%

Solid-Phase Synthesis of Oligonucleotides Containing a Site-Specific Psoralen Derivative

Kobertz

Essigmann

1997

J. Am. Chem. Soc.

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Tricyclic Systems: Central Carbocyclic Ring with Fused Five- and Six-membered Rings

Groziak

2008

Comprehensive Heterocyclic Chemistry III

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An Efficient Synthesis of a Furan-Side Furocoumarin Thymidine Monoadduct

Cited by 5 publications

References 32 publications

Synthesis of DNA Lesions and DNA-Lesion-Containing Oligonucleotides for DNA-Repair Studies

Synthesis of DNA Lesions and DNA-Lesion-Containing Oligonucleotides for DNA-Repair Studies

Solid-Phase Synthesis of Oligonucleotides Containing a Site-Specific Psoralen Derivative

Tricyclic Systems: Central Carbocyclic Ring with Fused Five- and Six-membered Rings

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