Synthesis of the enantiomers of the dual function 2‐nitroimidazole radiation sensitizer RB 6145

Sercel, Anthony D.; Beylin, Vladimir G.; Marlatt, M.; Leja, Boguslawa; Showalter, H. D. Hollis; Michel, A. G.

doi:10.1002/jhet.5570430625

Cited by 7 publications

(3 citation statements)

References 18 publications

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“…AcmSH was then used to displace the bromine in 1 to produce compound 2 in 68% yield. Finally, the ring opening of the oxazolidinone moiety of 2 was carried out in HOAc containing 31% HBr to afford the desired 2-bromoethylamine derivative in 27% yield (Scheme b). Thus, key bifunctional handle 3 can be rapidly prepared in three steps in an overall yield of 18%, which bodes well for its future application.…”

Section: Resultsmentioning

confidence: 99%

Cysteine-Aminoethylation-Assisted Chemical Ubiquitination of Recombinant Histones

Chu

Pan

et al. 2019

J. Am. Chem. Soc.

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Histone ubiquitination affects the structure and function of nucleosomes through tightly regulated dynamic reversible processes. The efficient preparation of ubiquitinated histones and their analogs is important for biochemical and biophysical studies on histone ubiquitination. Here, we report the CAACU (cysteine-aminoethylation assisted chemical ubiquitination) strategy for the efficient synthesis of ubiquitinated histone analogs. The key step in the CAACU strategy is the installation of an N-alkylated 2-bromoethylamine derivative into a recombinant histone through cysteine aminoethylation, followed by native chemical ligation assisted by Seitz’s auxiliary to produce mono- and diubiquitin (Ub) and small ubiquitin-like modifier (SUMO) modified histone analogs. This approach enables the rapid production of modified histones from recombinant proteins at about 1.5–6 mg/L expression. The thioether-containing isopeptide bonds in the products are chemically stable and bear only one atomic substitution in the structure, compared to their native counterparts. The ubiquitinated histone analogs prepared by CAACU can be readily reconstituted into nucleosomes and selectively recognized by relevant interacting proteins. The thioether-containing isopeptide bonds can also be recognized and hydrolyzed by deubiquitinases (DUBs). Cryo-electron microscopy (cryo-EM) of the nucleosome containing H2BKC34Ub indicated that the obtained CAACU histones were of good quality for structural studies. Collectively, this work exemplifies the utility of the CAACU strategy for the simple and efficient production of homogeneous ubiquitinated and SUMOylated histones for biochemical and biophysical studies.

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Section: Resultsmentioning

confidence: 99%

Cysteine-Aminoethylation-Assisted Chemical Ubiquitination of Recombinant Histones

Chu

Pan

et al. 2019

J. Am. Chem. Soc.

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“…The ring-opening reaction of mono-epoxy compounds with some simple silylamines for organic synthesis purposes has been reported through the use of different solvents including CH 2 Cl 2, Et 2 O, and THF and different catalysts such as BF 3 ·Et 2 O, AlCl 3 , LiBr, ZnCl 2 , and LiClO 4 , and so forth. Nevertheless, there are no reports on the use of difunctional DSBAs up to date for polymerization with diepoxys according to our best knowledge.…”

Section: Results and Discussionmentioning

confidence: 99%

Disilyl Bis(Secondary Amine)-Enabled Epoxy Ring-Opening and Silylotropic N → O Migration Leading to Low Dielectric Epoxy Copolymers

Duan

Mei

et al. 2021

Macromolecules

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This work presents a strategy for fabricating low dielectric epoxy copolymers through copolymerizing bisphenol A diglycidyl ether with N,N′-disilyl bis(secondary amine)s, a series of difunctional silylamines synthesized by silylation of bis(secondary amine)s. A study on the model reaction of monoepoxy with monofunctional silylamines identified that the reaction proceeded smoothly in tetrahydrofuran with Mg(ClO 4 ) 2 catalysis and mechanistically through sequential silylamine-induced epoxy ringopening and silylotropic N → O migration, a process with favorable Gibbs free energy changes as confirmed by density functional theory calculations. The copolymers demonstrated remarkably low dielectric constants and dielectric losses due to the formation of the low-polarizable silyloxyl instead of the hydroxyl group in polymerization and the enlarged molecular free volume. In addition, the copolymers showed desirable toughness, hydrophobicity, and thermal stability. As a tool to achieve these desirable features, the strategy developed in this work may find promising application in designing low dielectric epoxy resin materials for use in the microelectronic field.

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“…N,N′-Carbonyldiimidazole is used more frequently for carbonylation of amino alcohols [113]; representatives of a new class of antibacterial agents containing an oxazolidine fragment, linezolid 82, eperezolid 83, and others [114] were obtained using CDI from sugar derivatives 84 (Scheme 49). Sercel et al [123] synthesized N-(oxiran-2-ylmethyl)-substituted 1,3-oxazolidin-2-one 85 and examined its reactions with amines (Scheme 50). Mono-and diaryloxiranes 86 were studied as reagents in [124] (Scheme 51).…”

Section: Synthesis Of 13-oxazolidin-2-ones From Isocyanates and Othementioning

confidence: 99%

Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

2011

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Synthesis of the enantiomers of the dual function 2‐nitroimidazole radiation sensitizer RB 6145

Cited by 7 publications

References 18 publications

Cysteine-Aminoethylation-Assisted Chemical Ubiquitination of Recombinant Histones

Cysteine-Aminoethylation-Assisted Chemical Ubiquitination of Recombinant Histones

Disilyl Bis(Secondary Amine)-Enabled Epoxy Ring-Opening and Silylotropic N → O Migration Leading to Low Dielectric Epoxy Copolymers

Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

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