Chemistry of phosphodiesters, DNA and models. 3. Microgonotropens and their interactions with DNA. 1. Synthesis of the tripyrrole peptides dien-microgonotropen-a, -b, and -c and characterization of their interactions with dsDNA was written by He, Gong Xin;Browne, Kenneth A.;Groppe, Jay C.;Blasko, Andrei;Mei, Houng Yau;Bruice, Thomas C.. And the article was included in Journal of the American Chemical Society in 1993.Recommanded Product: Ethyl 4-nitro-1H-pyrrole-2-carboxylate This article mentions the following:
Exploration of the novel idea of employing a pyrrole nitrogen of a tripyrrole peptide minor groove binding agent to carry catalytic entities to the phosphates and major groove to DNA has been initiated with the synthesis of dien-microgonotropen-a, -b, and -c [I; R = (CH2)nN(CH2CH2CH2NMe2)2, n = 3-5] (II). Replacing the carboxyl terminal amidine and amino terminal formyl functionalities of distamycin (Dm) by CH2NMe2 and Ac substituents, resp., provides I (R = Me), which has greater stability in water than does Dm. The synthetic design allows the N-Me substituent on the central pyrrole of I (R = Me) to be replaced by connectors terminating in a dien ligand (II). The binding of I (R = Me) is about 20-fold weaker than the binding of II to calf thymus DNA, poly(dA-dT), and poly(dI-dC) due to the contribution of the polyamine substituents of the latter. The specificity and affinity of binding of II to the 5′-[32P] 167-bp EcoRI/RsaI restriction fragment of pBR322 was determined by DNase I footprint anal. Specific inhibition of cleavage was observed at each of the four potential A+T-rich binding sites after preincubation with II at concentrations as high as 50 μM. At 250 μM, binding at short heteropolymeric A+T secondary sites distal to the cluster of A+T-rich primary binding sites was observed At such higher concentrations of II, increased rates of enzymic cleavage at specific sequences were observed DNase I footprinting anal. of the 3′-labeled fragment provided complementary results. Electrophoretic migration of HaeIII restriction digest fragments of φX-174-RF DNA after preincubation with II was used to assess induction of gross conformational changes in DNA mols. As the concentration of the agents increases, the effect of the agents in changing the conformation of larger DNA fragments decreases in the order II (n = 5) > II (n = 4) > II (n = 3) ≫ Dm > Hoechst 33258. The electrophoretic mobilities of smaller DNA fragments are unaltered in the presence of the various agents. The dien-microgonotropens are much more effective in inducing changes than the sum of the Dm and bis[3-(dimethylamino)propyl]methylamine parts. This is due to the unique relationship between the minor groove binding portion of the dien-microgonotropens and the accompanying electrostatic complexing of the covalently attached dien moiety to the phosphodiester backbone of DNA. In the experiment, the researchers used many compounds, for example, Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7Recommanded Product: Ethyl 4-nitro-1H-pyrrole-2-carboxylate).
Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Recommanded Product: Ethyl 4-nitro-1H-pyrrole-2-carboxylate
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