100715-74-0Relevant academic research and scientific papers
Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases
Rempel,Withers
supporting information, p. 2592 - 2595 (2014/04/17)
2-Deoxy-2-fluoroglycosides bearing dibenzyl phosphate and phosphonate aglycones were synthesised and tested as covalent inactivators of several retaining α- and β-glycosidases. β-d-Gluco-, -manno- and -galacto-configured benzyl-benzylphosphonate derivatives efficiently inactivated β-gluco-, β-manno- and β-galactosidases, while α-gluco- and α-manno-configured phosphate and phosphonate derivatives served instead as slow substrates. This journal is the Partner Organisations 2014.
Tailoring the specificity and reactivity of a mechanism-based inactivator of glucocerebrosidase for potential therapeutic applications
Rempel, Brian P.,Tropak, Michael B.,Mahuran, Don J.,Withers, Stephen G.
supporting information; experimental part, p. 10381 - 10383 (2011/12/04)
Chaperoning an enzyme: Fluorosugar glycosidase inactivators with tunable phosphorus-based leaving groups react quickly with the catalytic nucleophile in β glucocerebrosidase (blue circle; Bn=benzyl). In Western blot analysis, Gaucher patient cells treated with these inactivators show increased intracellular levels of mutant enzyme, presumably because of increased transit from the endoplasmic reticulum (pale blue) to the lysosome (pale pink). Copyright
Phosphonic acid analogs of GABA through reductive dealkylation of phosphonic diesters with lithium trialkylborohydrides
Chowdhury, Sarwat,Muni, Niraj J.,Greenwood, Nicholas P.,Pepperberg, David R.,Standaert, Robert F.
, p. 3745 - 3748 (2008/02/13)
Lithium trialkylborohydrides were found to effect rapid monodealkylation of phosphonic diesters, and this reaction was applied to the synthesis of alkylphosphonic acid 2-aminoethyl esters [H2N(CH2)2OP(OH)R, 4], a little-ex
Probing for a hydrophobic a binding register in prostate-specific membrane antigen with phenylalkylphosphonamidates
Maung, Jack,Mallari, Jeremy P.,Girtsman, Teri A.,Wu, Lisa Y.,Rowley, Jennifer A.,Santiago, Nicholas M.,Brunelle, Alan N.,Berkman, Clifford E.
, p. 4969 - 4979 (2007/10/03)
A series of phenylalkylphosphonamidate derivatives of glutamic acid were synthesized and evaluated for their inhibitory potencies against PSMA. The greatest inhibitory potency was observed for the inhibitors 1f (n = 5) and 1g (n = 6) suggesting the presen
