Chemical Synthesis and Preliminary Structural Characterization of a Nitrous Acid Interstrand Cross-Linked Duplex DNA

Harwood, Eric A.; Sigurdsson, Snorri Th.; Edfeldt, N. B. Fredrik; Reid, and Brian R.; Hopkins, Paul B.

doi:10.1021/ja984426d

Cited by 91 publications

(85 citation statements)

References 22 publications

(30 reference statements)

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“…The use of two orthogonal protecting groups (denoted P1: DMTr and P2: Alloc or TBS) allowed the synthesis of palindromic sequences containing site-specific ICLs. [40,42] Scheme 5. ICL synthesis with postsynthetically modifiable ICL precursors.…”

Section: Discussionmentioning

confidence: 99%

“…A differential protection scheme of the nucleoside dimer was developed that allowed for the stepwise construction of the oligonucleotide flanking the ICL. Although this method of ICL synthesis imposes certain limitations in terms of accessible sequences and lengths of the ICL-containing oligonucleotides, it has led to the synthesis of ICLs formed by nitric oxide, [40] mimics of ICLs formed by alkylating agents [41,42] and artificial crosslinked base-pairs [43] in sufficient amounts for detailed structural characterization.…”

Section: Fanconi Anemia-linking Icls To Inherited Disease and Cancer mentioning

confidence: 99%

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DNA Interstrand Crosslinks: Natural and Drug‐Induced DNA Adducts that Induce Unique Cellular Responses

2005

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Section: Discussionmentioning

confidence: 99%

Section: Fanconi Anemia-linking Icls To Inherited Disease and Cancer mentioning

confidence: 99%

DNA Interstrand Crosslinks: Natural and Drug‐Induced DNA Adducts that Induce Unique Cellular Responses

2005

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“…Lemière has coupled primary arylamines with 4-chloro-3(2H)-pyridazinones to form compounds with possible analgesic and antiinflammatory properties. [211]. Improved yields were reported by De Riccardis and Johnson when using Cs 2 CO 3 .…”

Section: Arylation Of Primary Alkylaminesmentioning

confidence: 76%

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Hartwig

2002

Modern Arene Chemistry

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The transition metal catalyzed synthesis of arylamines by the reaction of aryl halides or triflates with primary or secondary amines has become a valuable synthetic tool for many applications. This process forms monoalkyl or dialkyl anilines, mixed diarylamines or mixed triarylamines, as well as N-arylimines, carbamates, hydrazones, amides, and tosylamides. The mechanism of the process involves several new organometallic reactions. For example, the CaN bond is formed by reductive elimination of amine, and the metal amido complexes that undergo reductive elimination are formed in the catalytic cycle in some cases by NaH activation. Side products are formed by b-hydrogen elimination from amides, examples of which have recently been observed directly. An overview that covers the development of synthetic methods to form arylamines by this palladium-catalyzed chemistry is presented. In addition to the synthetic information, a description of the pertinent mechanistic data on the overall catalytic cycle, on each elementary reaction that comprises the catalytic cycle, and on competing side reactions is presented. The review covers manuscripts that appeared in press before June 1, 2001. This chapter is based on a review covering the literature up to September 1, 1999. However, roughly one-hundred papers on this topic have appeared since that time, requiring an updated review.

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“…An oven-dried 100 mL two-necked round-bottomed flask was charged with the protected purine nucleoside 1 [31] …”

Section: Chemicals and Reagentsmentioning

confidence: 99%

Synthesis of the Fully Protected Phosphoramidite of the Benzene-DNA Adduct,N²-(4-Hydroxyphenyl)-2′-Deoxyguanosine and Incorporation of the Later into DNA Oligomers

Chenna¹,

Gupta

Bonala

et al. 2008

Nucleosides, Nucleotides and Nucleic Acids

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Chemical Synthesis and Preliminary Structural Characterization of a Nitrous Acid Interstrand Cross-Linked Duplex DNA

Cited by 91 publications

References 22 publications

DNA Interstrand Crosslinks: Natural and Drug‐Induced DNA Adducts that Induce Unique Cellular Responses

DNA Interstrand Crosslinks: Natural and Drug‐Induced DNA Adducts that Induce Unique Cellular Responses

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Synthesis of the Fully Protected Phosphoramidite of the Benzene-DNA Adduct,N²-(4-Hydroxyphenyl)-2′-Deoxyguanosine and Incorporation of the Later into DNA Oligomers

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Chemical Synthesis and Preliminary Structural Characterization of a Nitrous Acid Interstrand Cross-Linked Duplex DNA

Cited by 91 publications

References 22 publications

DNA Interstrand Crosslinks: Natural and Drug‐Induced DNA Adducts that Induce Unique Cellular Responses

DNA Interstrand Crosslinks: Natural and Drug‐Induced DNA Adducts that Induce Unique Cellular Responses

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Synthesis of the Fully Protected Phosphoramidite of the Benzene-DNA Adduct,N2-(4-Hydroxyphenyl)-2′-Deoxyguanosine and Incorporation of the Later into DNA Oligomers

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Synthesis of the Fully Protected Phosphoramidite of the Benzene-DNA Adduct,N²-(4-Hydroxyphenyl)-2′-Deoxyguanosine and Incorporation of the Later into DNA Oligomers