83701-40-0Relevant articles and documents
Azido Functionalized Nucleosides Linked to Controlled Pore Glass as Suitable Starting Materials for Oligonucleotide Synthesis by the Phosphoramidite Approach
Müggenburg, Frederik,Biallas, Alexander,Debiais, Mégane,Smietana, Michael,Müller, Sabine
supporting information, p. 6408 - 6416 (2021/11/30)
It has long been debated whether easily reducible azide groups can withstand the conditions of oligonucleotide synthesis by phosphoramidite chemistry. We have synthesized various 2′- and 3′-azido modified nucleosides and immobilized them on controlled pore glass (CPG) to be used as starting material for the synthesis of oligonucleotides (ONs) with 3′-terminal azide (attached to C2′ or C3′). In a model study, immobilized 3′-azidoadenosine was used as a starting block for the synthesis of a series of oligodeoxynucleotides (ODNs) of increasing length. Upon synthesis, the ODNs were enzymatically digested into monomers and analyzed by RP-HPLC. A peak corresponding to 3′-azidoadenosine was clearly identified in all samples. Quantitative analysis showed that 3′-azidoadenosine was present in nearly the expected ratio to deoxycytidine, which was used as an internal standard. Most importantly, the ratio remained the same for all three ODNs regardless of their length, demonstrating that a higher number of coupling cycles does not lead to higher degradation of the azide. Thus, 2′- or 3′-azido nucleosides attached to a solid support are excellent starting materials for the synthesis of oligonucleotides with 3′-terminal azide.
Polyfluorophenyl Ester-Terminated Homobifunctional Cross-Linkers for Protein Conjugation
Wang, Jian,Zhang, Ru-Yan,Wang, Ya-Cong,Chen, Xiang-Zhao,Yin, Xu-Guang,Du, Jing-Jing,Lei, Ze,Xin, Ling-Ming,Gao, Xiao-Fei,Liu, Zheng,Guo, Jun
supporting information, p. 1934 - 1938 (2017/09/13)
Along with N -hydroxysuccinimidyl, p -nitrophenyl, and phenylseleno esters, tetra- and penta-fluorophenyl esters were comparatively evaluated in term of their reactivity and hydrolytic stability. Their homobifunctional cross-linkers were prepared to conju
Efficient access to nonhydrolyzable initiator tRNA based on the synthesis of 3'-azido-3'-deoxyadenosine RNA
Steger, Jessica,Graber, Dagmar,Moroder, Holger,Geiermann, Anna-Skrollan,Aigner, Michaela,Micura, Ronald
supporting information; experimental part, p. 7470 - 7472 (2011/01/04)
Flexibility exercised: Hydrolysis-resistant 3′-aminoacyl-tRNA conjugates that contain a stable amide linkage instead of the natural ester are valuable substrates for biochemical studies of ribosomal processes. In a novel preparation of the stable E. coli initiator tRNA derivative 3′- (Nformylmethionyl) amino-tRNAfMet the key feature is the synthesis of 3′-azido oligoribonucleotides using a new functionalized solid support.
Minor groove DNA binders as antimicrobial agents. 1. Pyrrole tetraamides are potent antibacterials against vancomycin resistant Enteroccoci and methicillin resistant Staphylococcus aureus
Dyatkina, Natalia B.,Roberts, Christopher D.,Keicher, Jesse D.,Dai, Yuqin,Nadherny, Joshua P.,Zhang, Wentao,Schmitz, Uli,Kongpachith, Ana,Fung, Kevin,Novikov, Alexander A.,Lou, Lillian,Velligan, Mark,Khorlin, Alexander A.,Chen, Ming S.
, p. 805 - 817 (2007/10/03)
A new series of short pyrrole tetraamides are described whose submicromolar DNA binding affinity is an essential component for their strong antibacterial activity. This class of compounds is related to the linked bis-netropsins and bis-distamycins, but here, only one amino-pyrrole-carboxamide unit and an amidine tail is connected to either side of a central dicarboxylic acid linker. The highest degree of DNA binding, measured by compound-induced changes in UV melting temperatures of an AT-rich DNA oligomer, was observed for flat, aromatic linkers with no inherent bent, i.e., terephthalic acid or 1,4-pyridine-dicarboxylic acid. However, the antibacterial activity is critically linked to the size of the N-alkyl substiutent of the pyrrole unit. None of the tetraamides with the commonly used methyl-pyrrole showed antibacterial activity. Isoamyl- or cyclopropylmethylene-substituted dipyrrole derivatives have the minimum inhibitory concentrations in the submicromolar range. In vitro toxicity against human T-cells was studied for all compounds. The degree to which compounds inhibited cell growth was neither directly correlated to DNA binding affinity nor directly correlated to antibacterial activity but seemed to depend strongly on the nature of the N-alkyl pyrrole substituents.
