Phosphorus-containing amino acids with a P–C bond in the side chain or a P–O, P–S or P–N bond: from synthesis to applications

Arribat, Mathieu; Cavelier, Florine; Rémond, Emmanuelle

doi:10.1039/c9ra10917j

Cited by 20 publications

(26 citation statements)

References 130 publications

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“…Very recently, Rémond, Cavelier et al . summarized the synthesis of selected phosphorus‐containing α‐amino acids [20] . However, a comprehensive analysis on this vigorous subject, especially on the asymmetric transformations to chiral molecules, has no precedence.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

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Chiral amino acids featuring a phosphonate pendant arm are an important type of biologically active scaffold. Here in this review, we comprehensively summarize the modern synthetic methods towards asymmetric construction of chiral amino carboxylic‐phosphonic acid derivatives. The main streams of such interesting compounds include phosphono‐containing α‐, β‐, and γ‐amino acid derivatives, amino acid fluorophosphonate derivatives, amino acid cyclopropanylphosphonate derivatives, and bisphosphono‐amino acid derivatives. Chiral resolution protocols, chiral auxiliary‐directed syntheses, and valorization of the pool of abundant chiral amino acid resources remain contemporary concerns, and meanwhile catalytic enantioselective synthesis has also emerged as a potent strategy as demonstrated by the latest advances.magnified image

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Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

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“…Incorporation of phosphorus into amino acids has been reported to generate phosphonium ylides or β‐keto phosphonates, and further transformations lead to a diverse set of α,β‐unsaturated molecules [7] …”

Section: Introductionmentioning

confidence: 99%

Diversity‐Oriented Synthesis (DOS) of On‐DNA Peptidomimetics from Acid‐Derived Phosphonium Ylides

Sunkari

Siripuram

Flajolet

2023

Chemistry A European J

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The DNA-encoded library (DEL) technology represents a revolutionary drug-discovery tool with unprecedented screening power originating from the association of combinatorial chemistry and DNA barcoding. The chemical diversity of DELs and its chemical space will be further expanded as new DNA-compatible reactions are introduced. This work introduces the use of DOS in the context of on-DNA peptidomimetics. Wittig olefination of aspartic acid-derived on-DNA Wittig ylide, combined with a broad substrate scope of aldehydes, led to formation of on-DNA a,b-unsaturated ketones. The synthesis of on-DNA multi-peptidyl-ylides was performed by incorporating sequential amino acids onto a monomeric ylide. Di-, tri-and tetrameric peptidyl-ylides were validated for Wittig olefination and led to on-DNA a, b-unsaturated-based peptidomimetics, an important class of intermediates. One on-DNA aryl Wittig ylide was also developed and applied to Wittig olefination for synthesis of on-DNA chalcone-based molecules. Furthermore, DOS was used successfully with electron-deficient peptidomimetics and led to the development of different heterocyclic cores containing on-DNA peptidomimetics.

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“…Over the past two decades, the formation of carbonphosphorus (C-P) bond has proved to be one of the most prominent strategies in preparing a diverse range of biologically active organophosphorus compounds in medicinal chemistry, coordination chemistry, organic synthesis, and catalysis. [1][2][3][4][5][6] In this context, much effort has been devoted to improving the new strategies for the generating the C-P bond. Hence, the C-P bond construction catalyzed with transition metals can be modified efficiently by decreasing impressive costs and extra materials, also increasing selectivity and functional group tolerance.…”

Section: Introductionmentioning

confidence: 99%

Fe₃O₄@glutamate MOF functionalized with Co nanoparticles anchored dicyandiamde: As a capable heterogeneous and reusable nanocatalyst in C–P cross‐coupling reaction

Eftekhar

Khosravi

2022

Applied Organom Chemis

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Herein, we report an efficient, simple, coherent, and green benign synthesis of the C–P coupling reaction based on the Fe3O4@glutamate MOF functionalized with Co nanoparticle anchored dicyandiamide. The structure of the as‐prepared catalyst was characterized by a series of measurement techniques, including FT‐IR, XRD, BET, TEM, FE‐SEM, EDX, EDX‐mapping, VSM, TGA, and ICP‐OES. The aforementioned nanocatalyst with a unique structure exhibited excellent catalytic performance on various substrates towards the synthesis of C–P cross‐coupled products in good to high yields under mild conditions. This unique heterogeneous catalytic system kept relatively high catalytic activity after five recycle runs under the same reaction conditions.

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Phosphorus-containing amino acids with a P–C bond in the side chain or a P–O, P–S or P–N bond: from synthesis to applications

Abstract: Strategies for the preparation of phosphorus-containing amino acids and their utility in the organic chemistry, physico-chemistry, agrochemistry, and pharmacology fields are reported.

Cited by 20 publications

References 130 publications

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Diversity‐Oriented Synthesis (DOS) of On‐DNA Peptidomimetics from Acid‐Derived Phosphonium Ylides

Fe₃O₄@glutamate MOF functionalized with Co nanoparticles anchored dicyandiamde: As a capable heterogeneous and reusable nanocatalyst in C–P cross‐coupling reaction

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Phosphorus-containing amino acids with a P–C bond in the side chain or a P–O, P–S or P–N bond: from synthesis to applications

Abstract: Strategies for the preparation of phosphorus-containing amino acids and their utility in the organic chemistry, physico-chemistry, agrochemistry, and pharmacology fields are reported.

Cited by 20 publications

References 130 publications

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Diversity‐Oriented Synthesis (DOS) of On‐DNA Peptidomimetics from Acid‐Derived Phosphonium Ylides

Fe3O4@glutamate MOF functionalized with Co nanoparticles anchored dicyandiamde: As a capable heterogeneous and reusable nanocatalyst in C–P cross‐coupling reaction

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Product

Resources

About

Fe₃O₄@glutamate MOF functionalized with Co nanoparticles anchored dicyandiamde: As a capable heterogeneous and reusable nanocatalyst in C–P cross‐coupling reaction