66168-85-2Relevant articles and documents
Salama et al.
, p. 3781 (1978)
"Induced fit" in chiral recognition: Epimerization upon dimerization in the hierarchical self-assembly of helicate-type titanium(IV) complexes
Albrecht, Markus,Isaak, Elisabeth,Baumert, Miriam,Gossen, Verena,Raabe, Gerhard,Froehlich, Roland
, p. 2850 - 2853 (2011)
Undecided! A titanium(IV) triscatecholate bearing chiral ester groups shows different CD spectra in methanol and DMSO. The observation of different stereoisomers lies in the preferred conformation of the side groups in the monomer and dimer, which leads to different chiral induction in the different species. Copyright
Shedding Light on the Interactions of Hydrocarbon Ester Substituents upon Formation of Dimeric Titanium(IV) Triscatecholates in DMSO Solution
Albrecht, Markus,Baums, Julia,Fr?hlich, Roland,G?b, Christian,Isaak, Elisabeth,Joseph, Benjamin P.,Kwamen, A. Carel N.,Massomi, Ali,Oppel, Iris M.,Puttreddy, Rakesh,R?uber, Christoph,Raabe, Gerhard,Rissanen, Kari,Schlottmann, Marcel,Shen, Li,Van Craen, David,Ward, Jas S.
supporting information, p. 1396 - 1405 (2020/02/04)
The dissociation of hierarchically formed dimeric triple lithium bridged triscatecholate titanium(IV) helicates with hydrocarbyl esters as side groups is systematically investigated in DMSO. Primary alkyl, alkenyl, alkynyl as well as benzyl esters are stu
Diphenyl-benzo[1,3]dioxole-4-carboxylic acid pentafluorophenyl ester: A convenient catechol precursor in the synthesis of siderophore vectors suitable for antibiotic Trojan horse strategies
Baco, Etienne,Hoegy, Francoise,Schalk, Isabelle J.,Mislin, Gaetan L. A.
, p. 749 - 757 (2014/01/23)
Catechols are components of many metal-chelating compounds, including siderophores that are naturally occurring iron(iii) chelators excreted by microorganisms. Catechol derivatives are poorly soluble in organic media and the synthesis of catechol-containing molecules requires the use of protected catechol precursors with improved organic solubility. We therefore developed 2,2-diphenyl-benzo[1,3]dioxole-4-carboxylic acid pentafluorophenyl ester. This activated ester reacts with an amine functionalized scaffold to generate chelators in which the catechol functions are protected in the form of diphenyl-benzodioxole moieties. The catechol can subsequently be deprotected, at the end of the synthesis, with trifluoroacetic acid (TFA). This strategy was applied to the synthesis of two catechol compounds functionalized with a terminal propargyl extension. These two compounds were shown to promote iron uptake in Escherichia coli and Pseudomonas aeruginosa. These two compounds are suitable for use as vectors in antibiotic Trojan horse approaches, as they could be conjugated with azide-functionalized antibiotics using the Huisgen dipolar 1,3-cycloaddition.
