3855-45-6Relevant articles and documents
An efficient peptide ligation using azido-protected peptides via the thioester method
Katayama, Hidekazu,Hojo, Hironobu,Ohira, Tsuyoshi,Nakahara, Yoshiaki
, p. 5492 - 5494 (2008)
Azido-protected Fmoc-Lys-OH (Fmoc-Lys(N3)-OH) was synthesized from Fmoc-Lys-OH by the copper(II)-catalyzed diazo transfer method, and introduced to a peptide by the ordinary Fmoc-based solid-phase peptide synthesis. This azido peptide could be condensed with a peptide thioester by the Ag+-free thioester method without any significant side reactions. The azido group was easily reduced to an amino group by Zn powder after peptide condensation.
Site-directed spin-labeling of nucleic acids by click chemistry: Detection of abasic sites in duplex DNA by EPR spectroscopy
Jakobsen, Ulla,Shelke, Sandip A.,Vogel, Stefan,Sigurdsson, Snorri Th.
, p. 10424 - 10428 (2010)
This paper describes a spin label that can detect and identify local structural deformations in duplex DNA, in particular abasic sites. The spin label was incorporated into DNA by a new postsynthetic approach using click-chemistry on a solid support, which simplified both the synthesis and purification of the spin-labeled oligonucleotides. A nitroxide-functionalized azide, prepared by a short synthetic route, was reacted with an oligomer containing 5-ethynyl-2′-dU. The conjugation proceeded in quantitative yield and resulted in a fairly rigid linker between the modified nucleotide and the nitroxide spin label. The spin label was used to detect, for the first time, abasic sites in duplex DNA by X-band CW-EPR spectroscopy and give information about other structural deformations as well as local conformational changes in DNA. For example, reduced mobility of the spin label in a mismatched pair with T was consistent with the spin label displacing the T from the duplex. Addition of mercury(II) to this mispair resulted in a substantial increase in the motion of the spin label, consistent with formation of a metallopair between the T and the spin-labeled base that results in movement of the spin label out of the duplex and toward the solution. Thus, reposition of the spin label, when acting as a mercury(II)-controlled mechanical lever, can be readily detected by EPR spectroscopy. The ease of incorporation and properties of the new spin label make it attractive for EPR studies of nucleic acids and other macromolecules.
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Cavender,C.J.,Shiner,V.J.
, p. 3567 - 3569 (1972)
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Simultaneous and site-directed incorporation of an ester linkage and an azide group into a polypeptide by in vitro translation
Humenik, Martin,Huang, Yiwei,Safronov, Igor,Sprinzl, Mathias
, p. 4218 - 4224 (2009)
A method is presented by which an azide-containing side chain can be introduced into any internal position of a polypeptide chain by in vitro translation. For this, 2′-deoxy-cytidylyl-(3′→5′)- adenosine was acylated on the 3′(2′)-hydroxyl group of adenosine with 6-azido-2(S)-hydroxyhexanoic acid (AHHA), an α-hydroxy- and ε-azide derivative of l-lysine. The acylated dinucleotide was enzymatically ligated with a tRNA transcript to provide chemically stable E. coli suppressor AHHA-tRNACys(CUA). The esterase 2 gene from Alicyclobacillus acidocaldarius was modified by the amber stop codon (UAG) on position 118. Using AHHA-tRNACys(CUA) in an E. coli in vitro translation/transcription system, the site-directed introduction of an azide group linked to a backbone ester into the esterase polypeptide was achieved. The yield of the synthesized modified protein reached 80% compared to translation of the native esterase. Subsequently, azide coupling with an alkyne-modified oligodeoxynucleotide demonstrated the feasibility of this approach for conjugation of polypeptides.
Functional Assemblies Emerging in Complex Mixtures of Peptides and Nucleic Acid–Peptide Chimeras
Chotera, Agata,Sadihov, Hava,Cohen-Luria, Rivka,Monnard, Pierre-Alain,Ashkenasy, Gonen
, p. 10128 - 10135 (2018)
Striking synergy between nucleic acids and proteins is exhibited in living cells. Whether such mutual activity can be performed using simple supramolecular nucleic acid–peptide (NA-pep) architectures remains a mystery. To shed light on this question, we studied the emergence of a primitive synergy in assemblies of short DNA-peptide chimeras. Specifically, we characterized multiple structures forming along gradual mixing trajectory, in which a peptide solution was seeded with increasing amounts of NA-pep chimeras. We report on the systematic change from β-sheet-peptide-based fibrillar architectures into the spherical structures formed by the conjugates. Remarkably, we find that through forming onion-like structures, the conjugates exhibit increased DNA hybridization stability and bind small molecules more efficiently than the peptides or DNA alone. A brief discussion highlights the implications of our findings for the production of new materials and for research on the origin of life.
The synthesis of androstane brassinosteroid analogues with α-azido acid ester groups in position 17β
Hnilickova, Jaroslava,Kohout, Ladislav,Capdevila, Enric,Esteve, Ana,Vilaplana, Marc,Molist, Meritxell,Brosa, Carme,Swaczynova-Oklestkova, Jana,Slavikova, Barbora
, p. 1005 - 1010 (2010)
Androstane brassinosteroid analogues with α-azido acid ester groups in position 17β were synthesized from 2α,3α,17β- trihydroxy-5α-androstan-6-one after the protection of the 2α,3α-diols upon treatment with the corresponding α-azido acid and the subsequent deprotection of the diol grouping. Six new castasterone analogues were prepared. The biological activities were evaluated in two bioassays: a rice lamina inclination test and bean second internode bioassays. The activities of the new analogues differ in these two bioassays.
Octakis(3-azidopropyl)octasilsesquioxane: A versatile nanobuilding block for the efficient preparation of highly functionalized cube-octameric polyhedral oligosilsesquioxane frameworks through click assembly
Trastoy, Beatriz,Eugenia Perez-Ojeda,Sastre, Roberto,Chiara, Jose Luis
, p. 3833 - 3841 (2010)
A one-step synthesis of octa-kis(3-azidopropyl)octasilsesquioxane from commercially available octakis(3-aminopropyl)octasilsesquioxane has been developed through a highly effi-cient diazo-transfer reaction under very mild conditions. Nonaflyl azide is sho
Oxa-adamantyl cannabinoids
Ho, Thanh C.,Tius, Marcus A.,Nikas, Spyros P.,Tran, Ngan K.,Tong, Fei,Zhou, Han,Zvonok, Nikolai,Makriyannis, Alexandros
supporting information, (2021/03/14)
As a continuation of earlier work on classical cannabinoids bearing bulky side chains we report here the design, synthesis, and biological evaluation of 3′-functionalized oxa-adamantyl cannabinoids as a novel class of cannabinergic ligands. Key synthetic steps involve nucleophilic addition/transannular cyclization of aryllithium to epoxyketone in the presence of cerium chloride and stereoselective construction of the tricyclic cannabinoid nucleus. The synthesis of the oxa-adamantyl cannabinoids is convenient, and amenable to scale up allowing the preparation of these analogs in sufficient quantities for detailed in vitro evaluation. The novel oxa-adamantyl cannabinoids reported here were found to be high affinity ligands for the CB1 and CB2 cannabinoid receptors. In the cyclase assay these compounds were found to behave as potent and efficacious CB1 receptor agonists. Isothiocyanate analog AM10504 is capable of irreversibly labeling both the CB1 and CB2 receptors.
QUATERNARY ALKYL AMMONIUM BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
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, (2012/07/13)
Disclosed are compounds having at least one quaternary alkyl ammonium functionality. The compounds inhibit bacterial efflux pump inhibitors and are used in combination with an anti-bacterial agent to treat or prevent bacterial infections. These combinations can be effective against bacterial infections that have developed resistance to anti-bacterial agents through an efflux pump mechanism.
