Marked Differences in Base Selectivity between DNA and the Free Nucleotides upon Adduct Formation from Bay- and Fjord-Region Diol Epoxides

2000 ◽  
Vol 13 (9) ◽  
pp. 883-890 ◽  
Author(s):  
SreenivasaRao Vepachedu ◽  
Naiqi Ya ◽  
Haruhiko Yagi ◽  
Jane M. Sayer ◽  
Donald M. Jerina
Keyword(s):  
Adduct Formation ◽  
Diol Epoxides ◽  
Free Nucleotides

scholarly journals Computational Exploration of Dibenzo [a,l] Pyrene Interaction to DNA and its Bases: Possible Implications to Human Health

2020 ◽  
Vol 11 (4) ◽  
pp. 11272-11283
Keyword(s):  
Weak Interactions ◽  
Excision Repair ◽  
Computational Simulation ◽  
Environmental Pollutant ◽  
Adduct Formation ◽  
Dna Adduct ◽  
Enzymatic Reactions ◽  
Diol Epoxides ◽  
Computational Exploration ◽  
Cis And Trans

Dibenzo[a,l]pyrene (DBP), an environmental pollutant, undergoes a series of enzymatic reactions yielding electrophilic diastereomeric diol-epoxides (DEs) that subsequently bind to DNA covalently and hampers the healing mechanism of cascaded biological pathways resulting in onset of different diseases. In the proposed work, we meticulously investigated and elucidated the mechanistic details of DNA adduct formation and nucleotide excision repair (NER) pathway proteins interaction with all possible diastereomers of dibenzo[a,l]pyrene-diol-epoxides (DBPDEs) namely- (±)-anti-, (±)-syn-, trans- and cis- forms of (-)-anti- and (+)-syn- DBPDEs through a computational simulation study. Our findings revealed that (±)-anti- and (-)-syn-DBPDEs interact more strongly with dT20 while (+)-syn-DBPDE exhibits strong interaction with dG6. Moreover, cis- and trans-conformations of (-)-anti- and (+)-syn-DBPDEs depicted strong binding towards N6-dA. Furthermore, aforesaid metabolic intermediates exhibited weak interactions with NER proteins. This imbalance of interaction tendencies relatively favors the DNA-adduct formation than the NER pathway. Based on our computational data, a robust understanding of the underlying molecular mechanism(s) of DBP-DNA interactions may subsequently lead to the design of novel potential compounds to exert inhibition and block its DNA binding ability and eventually facilitate cancer prevention.

Addition of Tetrachloromethane to 1,5-Hexadiene

1992 ◽  
Vol 57 (2) ◽  
pp. 393-396 ◽  
Author(s):  
Martin Kotora ◽  
Milan Hájek
Keyword(s):  
Palladium Catalyst ◽  
Adduct Formation ◽  
High Yield ◽  
Reaction Conditions ◽  
Dibenzoyl Peroxide

The 2 : 1 adduct as the final product of the addition of tetrachloromethane to 1,5-hexadiene catalyzed by copper(I)-butylamine complex was obtained in high yield (96%) under mild reaction conditions. Predominant 1 : 1 adduct formation was observed in the presence of a palladium catalyst or dibenzoyl peroxide initiator.

Formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycine anion

1989 ◽  
Vol 54 (2) ◽  
pp. 440-445 ◽  
Author(s):  
Vladimír Macháček ◽  
Alexandr Čegan ◽  
Miloš Sedlák ◽  
Vojeslav Štěrba
Keyword(s):  
Nmr Spectroscopy ◽  
Dimethyl Sulfoxide ◽  
Equilibrium Constant ◽  
Mole Fraction ◽  
Nucleophilic Addition ◽  
Adduct Formation ◽  
First Case ◽  
C Nmr

The intramolecular nucleophilic addition of N-methyl-N-(2,4,6-trinitrophenyl)glycine anion in methanol-dimethyl sulfoxide mixtures produces spiro[(3-methyl-5-oxazolidinone)-2,1'-(2',4',6'-trinitrobenzenide)]. The spiro adduct has been identified by means of 1H and 13C NMR spectroscopy. This is the first case when the formation of a Meisenheimer adduct with carboxylate ion is observed. Logarithm of the equilibrium constant of adduct formation increases linearly with the mole fraction of dimethyl sulfoxide in its mixture with methanol.

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