67201-29-0Relevant articles and documents
Pd-catalyzed stereospecific azide substitution of α,β- unsaturated γ,δ-epoxy esters with double inversion of configuration
Miyashita, Masaaki,Mizutani, Taiku,Tadano, Genta,Iwata, Yasuhiro,Miyazawa, Masahiro,Tanino, Keiji
, p. 5094 - 5097 (2005)
(Chemical Equation Presented) Acyclic, cyclic, and optically active unsaturated γ,δ-epoxy esters are employed in a highly stereoselective synthesis of functionalized amino alcohols, amino acids, and α,α-disubstituted amino acids. The key step of the react
Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition
Kelly, James M.,Leeper, Finian J.
body text, p. 819 - 821 (2012/03/10)
The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic α,β-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles.
Aminodeoxychorismate synthase inhibitors from one-bead one-compound combinatorial libraries: "Staged" inhibitor design
Dixon, Seth,Ziebart, Kristin T.,He, Ze,Jeddeloh, Melissa,Yoo, Choong Leol,Wang, Xiaobing,Lehman, Alan,Lam, Kit S.,Toney, Michael D.,Kurth, Mark J.
, p. 7413 - 7426 (2007/10/03)
4-Amino-4-deoxychorismate synthase (ADCS) catalyzes the first step in the conversion of chorismate into p-aminobenzoate, which is incorporated into folic acid. We aim to discover compounds that inhibit ADCS and serve as leads for a new class of antimicrobial compounds. This report presents (1) synthesis of a mass-tag encoded library based on a "staged" design, (2) massively parallel fluorescence-based on-bead screening, (3) rapid structural identification of hits, and (4) full kinetic analysis of ADCS. All inhibitors are competitive against chorismate and Mg2+. The most potent ADCS inhibitor identified has a Ki of 360 μM. We show that the combinatorial diversity elements add substantial binding affinity by interacting with residues outside of but proximal to the active site. The methods presented here constitute a paradigm for inhibitor discovery through active site targeting, enabled by rapid library synthesis, facile massively parallel screening, and straightforward hit identification.
