Selective Phosphorylation on Primary Alcohols of Unprotected Polyols

Ladame, Sylvain; Claustre, Samantha; Willson, Michèle

doi:10.1080/10426500108040232

Cited by 14 publications

(7 citation statements)

References 9 publications

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“…Then, the pyridine nucleophile attacks intermediate II to form the highly reactive electrophilic phosphorus species phosphoryl pyridin‐1‐ium ( III ) . Finally, intermediate III is transformed into the mixed phosphonate 3 a through a substitution reaction with phenol 2 a through TS2 ,…”

Section: Figurementioning

confidence: 99%

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

et al. 2018

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A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive P species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf O/pyridine.

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Section: Figurementioning

confidence: 99%

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

et al. 2018

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“…The synthesis of 1,3‐BPGA analogues used in this study has been described elsewhere [30–32]. NADH, NAD + , 3‐phosphoglycerate (3‐PGA), ATP, rabbit muscle GAPDH and yeast phosphoglycerate kinase (PGK) were purchased from Sigma.…”

Section: Sources Of Substrates Cofactors and Inhibitorsmentioning

confidence: 99%

Crystal structure of Trypanosoma cruzi glyceraldehyde‐3‐phosphate dehydrogenase complexed with an analogue of 1,3‐bisphospho‐d‐glyceric acid

Ladame

Castilho²,

Silva³

et al. 2003

European Journal of Biochemistry

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We report here the first crystal structure of a stable isosteric analogue of 1,3-bisphospho-D-glyceric acid (1, bound to the catalytic domain of Trypanosoma cruzi glycosomal glyceraldehyde-3-phosphate dehydrogenase (gGAPDH) in which the two phosphoryl moieties interact with Arg249. This complex possibly illustrates a step of the catalytic process by which Arg249 may induce compression of the product formed, allowing its expulsion from the active site. Structural modifications were introduced into this isosteric analogue and the respective inhibitory effects of the resulting diphosphorylated compounds on T. cruzi and Trypanosoma brucei gGAPDHs were investigated by enzymatic inhibition studies, fluorescence spectroscopy, sitedirected mutagenesis, and molecular modelling. Despite the high homology between the two trypanomastid gGAPDHs (> 95%), we have identified specific interactions that could be used to design selective irreversible inhibitors against T. cruzi gGAPDH.

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“…Hence,w eh ypothesized that the terminal oxygen P V = Oo fd ialkylphosphonates 1 could be activated by Tf 2 Ot oa fford ap hosphonium intermediate I (Scheme 1d), [19] which would then be converted into TfOsubstituted phosphonate intermediate II through nucleophilic substitution reaction. [21] With this idea in mind, we explored the development of new electrophilic P-species using chemically inert dialkylphosphonates for af acile synthesis of mixed phosphonates.H erein, we describe am etal-free,c hloridereagent-free,a nd Tf 2 O-mediated activation of phosphonates for the synthesis of mixed phosphonates through direct aryloxylation/alkyloxylation strategies. [21] With this idea in mind, we explored the development of new electrophilic P-species using chemically inert dialkylphosphonates for af acile synthesis of mixed phosphonates.H erein, we describe am etal-free,c hloridereagent-free,a nd Tf 2 O-mediated activation of phosphonates for the synthesis of mixed phosphonates through direct aryloxylation/alkyloxylation strategies.…”

mentioning

confidence: 99%

“…[20] Finally,w ee nvisioned that the phosphonate intermediate II in presence of pyridine could be transformed into highly reactive pyridinium phosphonate intermediate III. [21] With this idea in mind, we explored the development of new electrophilic P-species using chemically inert dialkylphosphonates for af acile synthesis of mixed phosphonates.H erein, we describe am etal-free,c hloridereagent-free,a nd Tf 2 O-mediated activation of phosphonates for the synthesis of mixed phosphonates through direct aryloxylation/alkyloxylation strategies.…”

mentioning

confidence: 99%

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

et al. 2018

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Astrategy for the direct functionalization strategy of inertial dialkylp hosphonates with hydroxy compounds to affordd iverse mixed phosphonates with good yields and functional-group tolerance has been developed. Mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive P V species (phosphoryl pyridin-1-ium salt), ak ey intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf 2 O/pyridine.

show abstract

Selective Phosphorylation on Primary Alcohols of Unprotected Polyols

Cited by 14 publications

References 9 publications

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

Crystal structure of Trypanosoma cruzi glyceraldehyde‐3‐phosphate dehydrogenase complexed with an analogue of 1,3‐bisphospho‐d‐glyceric acid

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

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