Synthesis and biological activity of dehydrophos derivatives

Jiménez-Andreu, M. Mercedes; Quintana, Ainhoa Lucía; Aínsa, José A.; Sayago, Francisco J.; Cativiela, Carlos

doi:10.1039/c8ob03079k

Cited by 3 publications

(2 citation statements)

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“…It is a dehydrophosphonopeptide, which, after the cleavage of the peptide bond, provides an analog of dehydroalanine, which is then converted into methyl acetylphosphonate (compound 41, an analog of pyruvic acid), which is strongly antibacterial by acting most likely as antimetabolite of pyruvate ( Figure 6) [87]. Thus, it was considered as a lead compound for the design of novel antibacterial agents [88]. The non-typical and innovative is the application of its biosynthetic enzymes for obtaining new antibacterial phosphonopeptides [89].…”

Section: Phosphonopeptide Antibioticsmentioning

confidence: 99%

Phosphonates: Their Natural Occurrence and Physiological Role

Kafarski¹

2020

Contemporary Topics About Phosphorus in Biology and Materials

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The first natural compound containing carbon-to-phosphorus bond-ciliatine was discovered 60 years ago, and for four decades, phosphonates were considered simply as a biological curiosity. Finding the importance of these compounds in biogeochemical phosphorus cycling, their role in methane production, as well as discovery of numerous phosphonates and phosphonopeptides of promising antibacterial and antifungal activities has stimulated the development of studies on this class of compounds, especially on their metabolism and biochemistry. These studies are driven by the use of 31 P NMR and by a clever combination of genomics and innovative chemistry by using the method of selective labeling of metabolites. These studies revealed unusual and interesting chemistry of these compounds.

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Section: Phosphonopeptide Antibioticsmentioning

confidence: 99%

Phosphonates: Their Natural Occurrence and Physiological Role

Kafarski¹

2020

Contemporary Topics About Phosphorus in Biology and Materials

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“…On the other hand, concerning their role in peptides, interest has been growing since the structure [10] and the mode of action [11] of the dehydrophos peptide was determined, which includes a dehydroamino–phosphonate residue in its structure (Figure 1c). [3a] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of β‐Aryl‐α,β‐Dehydroaminophosphonates by Pd‐Catalyzed Fujiwara–Moritani C−C Coupling

Sáez,

Dalmau,

Sayago

et al. 2024

Eur J Org Chem

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The treatment of diethyl α,β‐dehydroaminophosphonate 1 with various arenes (ArH=toluene 2 a, benzene 2 b, anisole 2 c, bromobenzene 2 d, chlorobenzene 2 e, benzyl alcohol 2 f, p‐xylene 2 g) in acetic acid (AcOH) at 120 °C for 8 h in the presence of Pd(OAc)2 (10 % mol, OAc=acetate) and AgOAc (3.4 equivalents) results in the formation of the corresponding β‐aryl derivatives E‐Ar(H)C=C(NHAc)P(O)(OEt)2 3 a–3 g. The reaction proceeds through double C−H activation (arene and alkene) and subsequent C−C oxidative coupling (Fujiwara–Moritani reaction), processes catalyzed by Pd and assisted by Ag. The obtained products 3 a–3 g are isosteric analogs of phenylalanine and are obtained with high selectivity. Thus, geometrical E‐isomers have been obtained in all studied cases, however mixtures of ortho‐/meta‐/para‐isomers are observed when the activated position in the starting arene 2 is considered.

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