ArticlePhosphorus, sulfur, and silicon and the related elements2019
New Chirally Modified Bisphosphonates for Synthesis of Individual Beta,Gamma-CHX-Deoxynucleotide Diastereomers.
Article in Phosphorus, sulfur, and silicon and the related elements, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Recent advances in the chemistry of α-hydoxyphosphonates: synthesis, reactivity, biological applications and theoretical study: a review from 2010 to 2025.RSC advances · 2026Review
- Synthetic Strategies to Access Fluorinated Azoles.European journal of organic chemistry · 2025Article
- Recent trends in ionic liquid-mediated synthesis of thiazoles: toward greener methodologies.RSC advances · 2025Review
- Uridine Bisphosphonates Differentiate Phosphoglycosyl Transferase Superfamilies.Journal of the American Chemical Society · 2024Article
- Metal-Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SOAngewandte Chemie (International ed. in English) · 2021Article
- Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives.Chemical science · 2020Article
- Phosphonopeptides containing free phosphonic groups: recent advances.RSC advances · 2020Review
- Rapid Entry into Biologically Relevant α,α-Difluoroalkylphosphonates Bearing Allyl Protection-Deblocking under Ru(II)/(IV)-Catalysis.Organic letters · 2019Article
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Authors and funding
6 authors.
Funding
Abstract
Individual diastereomers of CXY bisphosphonate analogues of dNTPs or NTPs are useful chemical stereoprobes to investigate interactions within the chiral active site environment of enzymes such as polymerases and kinases. We previously reported synthetic access to β,γ-CHX-dGTPs (X = F or Cl) via a bisphosphonate synthon with an (R)-methyl mandelate auxiliary and have extended this approach to dTTP and dATP analogues. As removal of the chiral auxiliary by (Pd/C) hydrogenolysis is incompatible with the cytosine heterocycle and also with X = Br, we have now designed bisphosphonate synthons using (R)-(+)-α-ethylbenzylamine or methyl (R)-(-)-phenylglycine auxiliaries and equipped with an o-nitrobenzyl ester protecting group allowing photochemical deprotection. These new synthons have made possible the first syntheses of individual dCTP and monobromo-substituted dNTP β,γ-CHX diastereomers.
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