82782-85-2Relevant articles and documents
Synthesis of Photochromic 1,2-Dihetarylethene Using Regioselective Acylation of Thienopyrroles
Krayushkin, Michael M.,Yarovenko, Vladimir N.,Semenov, Stanislav L.,Zavarzin, Igor V.,Ignatenko, Anatoliy V.,Martynkin, Andrey Yu.,Uzhinov, Boris M.
, p. 3879 - 3881 (2002)
(Matrix Presented) The influence of catalysts, acid chlorides, and solvents in the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. Conditions for the regioselective acylation processes were found. Thienopyrrole-based photoc
Regioselective acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5- carboxylate
Yarovenko,Semenov,Zavarzin,Ignatenko,Krayushkin
, p. 451 - 456 (2003)
The influence of catalysts, acid chlorides, and solvents on the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. The use of AlCl3 allows the regioselective introduction of the acyl group into position 3 to be performed, whereas the acyl group is regioselectively introduced into position 6 of thienopyrrole when SnCl4 is used.
Synthesis and characterization of S,N-heterotetracenes
Vogt, Astrid,Henne, Florian,Wetzel, Christoph,Mena-Osteritz, Elena,B?uerle, Peter
supporting information, p. 2636 - 2644 (2020/12/31)
The synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and nitrogen heteroatoms were synthesized in multistep synthetic routes. A Buchwald-Hartwig amination of brominated precursors, thermolysis of azide precursors, and a Cadogan reaction of nitro-substituted precursors were successfully applied to eventually build-up pyrrole rings to stable and soluble fused systems. The various obtained heteroatom sequences 'SSNS' (SN4), 'SNNS' (SN4''), and 'NSSN' (SN4') allowed for evaluation of structure-property relationships relative to the sulfur analogue tetrathienoacene ('SSSS'). In line with the results for the whole series of S,N-heteroacenes, we find that replacement of sulfur by nitrogen atoms in the tetra- and hexacyclic systems leads to a red-shift in absorption, a decrease in oxidation potential and energy gap. On the other hand, the replacement of a thiophene ring by benzene leads to the opposite effects.
Chemical Evolution of a Bacterial Proteome
Hoesl, Michael Georg,Oehm, Stefan,Durkin, Patrick,Darmon, Elise,Peil, Lauri,Aerni, Hans-Rudolf,Rappsilber, Juri,Rinehart, Jesse,Leach, David,S?ll, Dieter,Budisa, Nediljko
supporting information, p. 10030 - 10034 (2015/08/19)
We have changed the amino acid set of the genetic code of Escherichia coli by evolving cultures capable of growing on the synthetic noncanonical amino acid L-β-(thieno[3,2-b]pyrrolyl)alanine ([3,2]Tpa) as a sole surrogate for the canonical amino acid L-tryptophan (Trp). A long-term cultivation experiment in defined synthetic media resulted in the evolution of cells capable of surviving Trp→[3,2]Tpa substitutions in their proteomes in response to the 20 899 TGG codons of the E. coli W3110 genome. These evolved bacteria with new-to-nature amino acid composition showed robust growth in the complete absence of Trp. Our experimental results illustrate an approach for the evolution of synthetic cells with alternative biochemical building blocks.