Phosphorus in Chemical Biology and Medicinal Chemistry

doi:10.1002/9783527672240.ch10

Cited by 6 publications

(2 citation statements)

References 184 publications

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“…The modified cyclo-TP is then hydrolyzed with tetrabutylammonium hydroxide (TBA-OH), giving modified linear triphosphates 20-22 in yields between 54 and 82 %. Although this reagent has not yet been used with nucleosides, its reactivitywith MeOH and EtOH (17,18)h as been studied.…”

Section: Direct Modification Of Cyclo-tpmentioning

confidence: 99%

“…The potential of 1 to directly generatem odified triphosphate esters using alcohols is a highly appealing strategy. [17] The reactions should proceed through am odifiedc yclo-TP monoester that is then linearized with water (or other nucleophiles). Despite initial efforts in the 1960s [18] and 70s, [19] this reaction has only been transformed into au seful application severald ecades later.T he activation of cyclo-TP 1 with mesitylene chloride and DABCO [20] is the first example of as ynthetically broadly useful application.…”

Section: Introductionmentioning

confidence: 99%

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Cyclotriphosphate: A Brief History, Recent Developments, and Perspectives in Synthesis

Bezold

Dürr

Singh

et al. 2019

Chemistry A European J

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There has been a recent upsurge in the study and application of approaches utilizing cyclotriphosphate 1 (cyclo‐TP, also known as trimetaphosphate, TMP) and/or proceeding through its analogues in synthetic chemistry to access modified oligo‐ and polyphosphates. This is especially useful in the area of chemical nucleotide synthesis, but by no means restricted to it. Enabled by new high yielding and easy‐to‐implement methodologies, these approaches promise to open up an area of research that has previously been underappreciated. Additionally, refinements of concepts of prebiotic phosphorylation chemistry have been disclosed that ultimately rely on cyclo‐TP 1 as a precursor, placing it as a potentially central compound in the emergence of life. Given the importance of such concepts for our understanding of prebiotic chemistry in combination with the need to readily access modified polyphosphates for structural and biological studies, this paper will discuss selected recent developments in the field of cyclo‐TP chemistry, briefly touch on ultraphosphate chemistry, and highlight areas in which further developments can be expected.

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Section: Direct Modification Of Cyclo-tpmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cyclotriphosphate: A Brief History, Recent Developments, and Perspectives in Synthesis

Bezold

Dürr

Singh

et al. 2019

Chemistry A European J

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Development of Fluorophosphoramidate as a Biocompatibly Transformable Functional Group and its Application as a Phosphate Prodrug for Nucleoside Analogs

et al. 2022

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Synthetic phosphate-derived functional groups are important for controlling the function of bioactive molecules in vivo. Herein we describe the development of a new type of biocompatible phosphate analog, a fluorophosphoramidate (FPA) functional group that has characteristic PÀ F and PÀ N bonds. We found that FPA with a primary amino group was relatively unstable in aqueous solution and was converted to a monophosphate, while FPA with a secondary amino group was stable. Furthermore, by improving the molecular design of FPA, we developed a reaction in which a secondary amino group is converted to a primary amino group in the intracellular environment and clarified that the FPA group functions as a phosphate prodrug of nucleoside. Various FPA-gemcitabine derivatives were synthesized and their toxicity to cancer cells were evaluated. One of the FPA-gemcitabine derivatives showed superior toxicity compared with gemcitabine and its ProTide prodrug, which methodology is widely used in various nucleoside analogs, including anti-cancer and anti-virus drugs.

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Rapid Synthesis of Nucleoside Triphosphates and Analogues

Ripp

Singh

Jessen

2020

CP Nucleic Acid Chemistry

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Basic Protocol 2: Synthesis of 3-azidothymidine 5-γ-P-propargylamido triphosphates and analogues Basic Protocol 3: Synthesis of 2-deoxythymidine 5-γ-P-propargylamido triphosphate (15) Basic Protocol 4: Synthesis of adenosine 5-γ-P-amido triphosphate (19) and adenosine 5-γ-P-propargylamido triphosphate (20) Basic Protocol 5: Synthesis of d4T 5-γ-propargylamido β,γ-(difluoromethylene)triphosphate Support Protocol: Synthesis of diisopropylphosphoramidous dichloride

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Phosphorus in Chemical Biology and Medicinal Chemistry

Cited by 6 publications

References 184 publications

Cyclotriphosphate: A Brief History, Recent Developments, and Perspectives in Synthesis

Cyclotriphosphate: A Brief History, Recent Developments, and Perspectives in Synthesis

Development of Fluorophosphoramidate as a Biocompatibly Transformable Functional Group and its Application as a Phosphate Prodrug for Nucleoside Analogs

Rapid Synthesis of Nucleoside Triphosphates and Analogues

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