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Replication across O6-methylguanine activates futile cycling of DNA mismatch repair attempts assisted by the chromatin remodeling enzyme Smarcad1.
J Biochem
January 2025
Faculty of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan.
SN1-type alkylating reagents generate O6-methylguanine (meG) lesions that activate the mismatch repair (MMR) response. Since post-replicative MMR specifically targets the nascent strand, meG on the template strand is refractory to rectification by MMR and, therefore, can induce non-productive MMR reactions. The cycling of futile MMR attempts is proposed to cause DNA double-strand breaks in the subsequent S phase, leading to ATR-checkpoint-mediated G2 arrest and apoptosis.
View Article and Find Full Text PDFMutation signatures specific to DNA alkylating agents in yeast and cancers.
Nucleic Acids Res
April 2020
Genome Integrity and Structural Biology Laboratory, National Institute of Environmental Health Sciences, US National Institutes of Health, Research Triangle Park, NC 27709, USA.
Alkylation is one of the most ubiquitous forms of DNA lesions. However, the motif preferences and substrates for the activity of the major types of alkylating agents defined by their nucleophilic substitution reactions (SN1 and SN2) are still unclear. Utilizing yeast strains engineered for large-scale production of single-stranded DNA (ssDNA), we probed the substrate specificity, mutation spectra and signatures associated with DNA alkylating agents.
View Article and Find Full Text PDFRecent advances in the synthesis and applications of α-(trifluoromethyl)styrenes in organic synthesis.
Chem Commun (Camb)
November 2019
Department of Chemistry, Lishui University, No. 1, Xueyuan Road, Lishui City, 323000, P. R. China.
α-Trifluoromethylstyrene derivatives are versatile synthetic intermediates for the preparation of more complex fluorinated compounds. Much attention has been paid to these compounds by the organic chemistry community, because they have been successfully utilized in C-F bond activation in a CF3 group, mainly including anionic SN2'-type substitution, cationic SN1'-type substitution, ipso-substitution and defluorinative functionalization with transition metals or photoredox catalysts. In addition, transition metal-catalyzed cycloaddition reactions of α-trifluoromethylstyrenes have been developed for the construction of cycloalkanes and cycloalkenes containing fluoro or trifluoromethyl groups.
View Article and Find Full Text PDFLewis acid promoted fluorine-alkoxy group exchange reactions for the synthesis of 5-alkoxy-4,4-difluoroisoxazoline systems.
Org Biomol Chem
March 2019
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
Fluorine-alkoxy group exchange reactions of fluorinated isoxazoline derivatives promoted by Lewis acids to give various 5-alkoxylated 4,4-difluoroisoxazolines via SN1 type processes in good to excellent yields are reported. Sterically demanding phenol substrates such as 2,6-diphenylphenol gave novel aryl substituted products via electrophilic aromatic substitution.
View Article and Find Full Text PDFFrom QCA (Quantum Cellular Automata) to Organocatalytic Reactions with Stabilized Carbenium Ions.
Chem Rec
June 2016
Alma Mater Studiorum Università di Bologna, Dipartimento di Chimica "G. Ciamician", Via Selmi 2, 40126, Bologna, Italy.
What do quantum cellular automata (QCA), "on water" reactions, and SN 1-type organocatalytic transformations have in common? The link between these distant arguments is the practical access to useful intermediates and key products through the use of stabilized carbenium ions. Over 10 years, starting with a carbenium ion bearing a ferrocenyl group, to the 1,3-benzodithiolylium carbenium ion, our group has exploited the use of these intermediates in useful and practical synthetic transformations. In particular, we have applied the use of carbenium ions to stereoselective organocatalytic alkylation reactions, showing a possible solution for the "holy grail of organocatalysis".
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