717119-80-7Relevant academic research and scientific papers
Synthesis of 18F-labelled biotin analogues
Blom, Elisabeth,Itsenko, Oleksiy,Langstroem, Bengt
, p. 681 - 683 (2011)
A one-step 18F-labelling strategy was used to prepare three labelled analogues of the vitamin biotin, which can be useful as tracers because of biotin's high affinity for avidin. The labelled compounds were obtained in decay-corrected yields of up to 35% and specific radioactivity of 320 GBq/μmol. When evaluated in situ, the analogues showed good affinity for avidin: 60-75% of the radiolabelled compounds were bound to avidin within 5 minutes. The binding was site-specific, as shown by blocking experiments with native biotin. Copyright
Mechanistic Investigation on Copper–Arylacetylide Polymerization and Sensing Applications
Liang, Quanduo,Chang, Xiaoyong,Su, Ya-qiong,Mugo, Samuel M.,Zhang, Qiang
, p. 18014 - 18021 (2021)
Exploration of new polymerization reactions is very intriguing in fundamental and practical research, which will advance reaction theories and produce various functional materials. Herein, we report a new polymerization method based on the reaction of CuI and arylacetylide, which generates linear polymers with high molecular weight and low polydispersity index of molecular weight. The Cu–arylacetylide polymerization exhibits different characteristics with traditional polymerizations such as mild reaction temperature, air atmosphere reaction, high molecular weight, fast polymerization rate, and imprecise molar ratio between monomers. The bond formation path and activation energy of each step was investigated by density functional theory calculations to understand the reaction mechanism. The poly(Cu-arylacetylide)s exhibit strong fluorescence emission and inherent semiconductive properties, which have been used to fabricate an electronic device for streptavidin sensing.
Tandem Wittig/Diels-Alder diversification of genetically encoded peptide libraries
Triana, Vivian,Derda, Ratmir
, p. 7869 - 7877 (2017)
In this paper, we developed a tandem of two carbon-carbon bond-forming reactions to chemically diversify the libraries of peptides displayed on a bacteriophage. The Wittig reaction of a biotin-ester from a stabilized phosphorane ylide with model peptides containing N-terminal glyoxal exhibits reaction rates of 0.07 to 5 M-1 s-1 in water at pH 6.5-8. The log(k) scaled linearly with pH from pH 6 to 8; above pH 9 the reaction is accompanied by the hydrolysis of the ester functionality. Capture of the phage displaying the biotinylated product by streptavidin beads confirmed the rate of this reaction in a library of 108 peptides (k = 0.23 M-1 s-1 at pH = 6.5) and also confirmed the regioselectivity of this modification. Olefins introduced into the Wittig reaction can act as Michael acceptors: addition of glutathione, cysteamine, and DYKDDDDKC ( FLAG-Cys ) peptide occurs with k = 0.12-4.1 M-1 s-1 at pH 7.8. Analogous reactions with the DYKDDDDKC peptide take place on phage-displayed peptides modified via the Wittig reaction. This reaction is manifested as a progressive emergence of a FLAG-epitope on the phage and detected by the capture of this phage using an anti-FLAG antibody. Olefins introduced into the Wittig reaction also act as dienophiles in the Diels-Alder reaction with cyclopentadiene. The conversion of the dienophile to norbornene-like adducts on the phage was observed by monitoring the disappearance of the thiol-reactive olefin on the phage. This report broadens the reaction scope of genetically-encoded peptide libraries displayed on the phage, expanding the structural diversity of these platforms and increasing their potential to be used in screening against important protein targets. The possibility of monitoring tandem reactions by the use of different labels illustrates the feasibility of obtaining highly functionalized peptides with chemical motifs impossible to achieve using conventional translational machinery.
Determination of the bioavailability of biotin conjugated onto shell cross-linked (SCK) nanoparticles
Qi, Kai,Ma, Qinggao,Remsen, Edward E.,Clark Jr., Christopher G.,Wooley, Karen L.
, p. 6599 - 6607 (2004)
Shell cross-linked nanoparticles (SCKs) presenting surface- and bioavailable biotin functional groups were synthesized via a mixed micelle methodology, whereby co-micellization of chain terminal biotinylated poly(acrylic acid)-b-poly(methyl acrylate) (PAA-b-PMA) and nonbiotinylated PAA-b-PMA were cross-linked in an intramicellar fashion within the shell layer of the mixed micelles, between the carboxylic acid groups of PAA and the amine functionalities of 2,2′-(ethylenedioxy)diethylamine. The hydrodynamic diameters (Dh) of the micelles and the SCKs with different biotinylated block copolymer contents were determined by dynamic light scattering (DLS), and the dimensions of the SCKs were characterized with tapping-mode atomic force microscopy (AFM) and transmission electron microscopy (TEM). The amount of surface-available biotin was tuned by varying the stoichiometric ratio of the biotinylated PAA-b-PMA versus the nonbiotinylated PAA-b-PMA, as demonstrated with solution-state, binding interaction analyses, an avidin/HABA (avidin/4′-hydroxyazobenzene-2-carboxylic acid) competitive binding assay, and fluorescence correlation spectroscopy (FCS). The avidin/HABA assay found the amount of available biotin at the surface of the biotinylated SCK nanoparticles to increase with increasing biotin-terminated block copolymer incorporation, but to be less than 25% of the theoretical value. FCS measurements showed the same trend.
One-step synthesis of low polydispersity, biotinylated poly(N- isopropylacrylamide) by ATRP
Bontempo, Debora,Li, Ronald C.,Ly, Tiffany,Brubaker, Carrie E.,Maynard, Heather D.
, p. 4702 - 4704 (2005)
Low polydispersity poly(N-isopropylacrylamide) with a biotin end-group was obtained in one step from a biotinylated initiator for atom transfer radical polymerization and interacted with streptavidin to generate the thermosensitive polymerprotein conjugate. The Royal Society of Chemistry 2005.
