724-18-5Relevant academic research and scientific papers
A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation
Christian, Alec H.,Jia, Shang,Cao, Wendy,Zhang, Patricia,Meza, Arismel Tena,Sigman, Matthew S.,Chang, Christopher J.,Toste, F. Dean
supporting information, p. 12657 - 12662 (2019/09/04)
We report a data-driven, physical organic approach to the development of new methionine-selective bioconjugation reagents with tunable adduct stabilities. Statistical modeling of structural features described by intrinsic physical organic parameters was applied to the development of a predictive model and to gain insight into features driving the stability of adducts formed from the chemoselective coupling of oxaziridine and methionine thioether partners through Redox Activated Chemical Tagging (ReACT). From these analyses, a correlation between sulfimide stabilities and sulfimide ν (C=O) stretching frequencies was revealed. We exploited the rational gains in adduct stability exposed by this analysis to achieve the design and synthesis of a bis-oxaziridine reagent for peptide stapling. Indeed, we observed that a macrocyclic peptide formed by ReACT stapling at methionine exhibited improved uptake into live cells compared to an unstapled congener, highlighting the potential utility of this unique chemical tool for thioether modification. This work provides a template for the broader use of data-driven approaches to bioconjugation chemistry and other chemical biology applications.
Preparation of a novel polystyrene-based urea resin
Meusel, Manuela,Gütschow, Michael
, p. 2231 - 2233 (2007/10/03)
A urea-functionalized polystyrene-resin with a Rink linker was prepared by adaptation of a solution-phase synthesis to solid-phase chemistry. Thereby, a resin-bound acylurea was formed by reacting a Rink-amide resin with trichloroacetyl isocyanate, followed by the thermal removal of the trichloroacetyl group and thus generating the unsubstituted solid-supported urea.
Ureas in Organic Synthesis. XI. Reactions of Arylcarbinols with Carbamides in Synthesis of Biologically Active Arylmethylureas
Bakibaev, A. A.
, p. 1433 - 1437 (2007/10/03)
The reaction of arylcarbinols with carbamide in the presence of acids affords the corresponding arylmethylureas.
