22879-79-4Relevant academic research and scientific papers
Mechanisms of Decarboxylation of Carboxybiotin
Tipton, Peter A.,Cleland, W. W.
, p. 5866 - 5869 (1988)
Carboxylation is decarboxylated by two different mechanisms at low pH, where the N 1' carboxyl is protonated (pK 4.25 at 2 deg C) and at high pH where it is ionized.The low-pH mechanism has a rate constant of 5.9 X 10-3min-1 at 2 deg C (activation energy 33 kcal/mol), while the high - pH one has a rate constant of 4.6 X 10-3min-1 at 25 deg C, with the two mechanisms showing equal rates at 25 deg C at pH 6.4.At pH 8 the D2O solvent isotope effect is 1.1 with a curved proton inventory, while at pH 3.4 the value is 1.6 with a linear proton inventory.The 13C isotope effect on decarboxylation is 1.023 at pH 8.2, but 1.012 for the lo w-pH reaction.The low-pH mechanism probably involves concerted protonation of N 1' and C - N bond cleavage, with an early transition state in which proton motion is ahead of C - N bond breaking.The high - pH mechanism has a moderately early transition state and gives the enolate as the product, with the small solvent isotope effect presumably arising from changes in the fractionation factors of protons in water hydrogen-bonded to the ureido oxygen.
Synthetic studies on d-biotin, part 9.1) An improved asymmetric synthetic route to d-biotin via Hoffmann-Roche lactone-thiolactone approach
Chen, Fen-Er,Jia, Hui-Qing,Chen, Xu-Xiang,Dai, Hui-Fang,Xie, Bin,Kuang, Yun-Yan,Zhao, Jian-Feng
, p. 743 - 746 (2005)
An efficient and highly stereoselective total synthesis of d-biotin has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2) with an overall yield of 33%. Polymer-supported oxazaborolidine- catalyzed asymmetric reduction of meso-cyclic imide 4 constitutes the key synthetic step in introducing stereogenic centers into the d-biotin molecule.
Biotin derivatives carrying two chelating DOTA units. Synthesis, in vitro evaluation of biotinidases resistance, avidin binding, and radiolabeling tests
Pratesi, Alessandro,Bucelli, Francesca,Mori, Ilaria,Chinol, Marco,Verdoliva, Antonio,Paganelli, Giovanni,Rivieccio, Vincenzo,Gariboldi, Lucia,Ginanneschi, Mauro
, p. 432 - 440 (2010)
The synthesis of four biotin derivatives carrying two DOTA moieties for each ligand (BisDOTA set) is reported, for increasing radiation/dose ratio and improving efficiency in the pretargeted avidin-biotin radioimmunotherapy. The biotin-containing scaffold of two BisDOTAwas similar to the mono-DOTA derivative previously described. Then the scaffold was elongated by trifunctionalized spacers of different length and conjugated with one of the COOH groups of two DOTA. Two others were prepared starting from a on-resin lysine residue. The lysine R-NH2 was bonded to biotin, and then spacers were appended to the ε-NH2 and conjugated with two DOTA molecules. One compound contained a p-aminobenzoic acid spacer, which ensured higher head-to-tail distance and increased rigidity of the chain. These last two compounds had a very high ability to bond avidin and were labeled with 90Y at high specific activity. All the compounds were resistant to the action of serum biotinidases. 2009 American Chemical Society.
Isotope and Affinity Tags in Photoreactive Substance P Analogues to Identify the Covalent Linkage within the NK-1 Receptor by MALDI-TOF Analysis
Sachon, Emmanuelle,Tasseau, Olivier,Lavielle, Solange,Sagan, Sandrine,Bolbach, Gerard
, p. 6536 - 6543 (2003)
Photoreactive analogues of substance P (biotin sulfone-spacer (amino pentanoic or Gly 3)-Arg-Pro-Lys-Pro-(pBzl)-Phe-Gln-Phe-Phe-Gly-Leu-Met(O 2)NH2) with or without isotope (deuterium) labeling have been synthesized. Deuteriums were present on (d)-biotin or epibiotin sulfone (D3), on the Gly3 spacer linker (D6), or on the Gly in position 9 of SP (D2). Therefore, peptide analogues could be either unlabeled or tri-, penta-, or hexadeuterated. Results obtained with the use of these peptide analogues show that (d)-biotin sulfone and epibiotin sulfone are not recognized with the same affinity by streptavidin, with (d)-biotin sulfone displaying better affinity for the protein. Photolabeling of the human NK-1 receptor with a 1:1 molar ratio of nondeuterated and deuterated photoreactive substance P (SP) analogues in position 5, followed by combined digestions, purification, and MALDI-TOF mass spectrometry analysis, made the identification of the domain of the receptor covalently linked by the photoreactive SP analogue easier. Indeed, doublets in mass spectra were specific for the covalent complex whereas single peaks could be attributed to contaminating species. This method is particularly suitable when minute amounts of complex have to be analyzed, as in the case of highly hydrophobic G-protein coupled receptors.
Selective modification of sulfamidate-containing peptides
Busto, Jesús H.,Jiménez-Osés, Gonzalo,Mazo, Nuria,Navo, Claudio D.,Peregrina, Jesús M.
, p. 6265 - 6275 (2020)
Hybrid peptides whose N-terminal residues are activated in the form of α-methylisoserine-derived cyclic sulfamidates exhibit rich reactivity as electrophiles, allowing site- and stereoselective modifications at different backbone and side chain positions.
Highly enantioselective methanolysis of meso-cyclic anhydride mediated by bifunctional thiourea cinchona alkaloid derivatives: Access to asymmetric total synthesis of (+)-biotin
Xiong, Fei,Xiong, Fang-Jun,Chen, Wen-Xue,Jia, Hui-Qing,Chen, Fen-Er
, p. 1078 - 1082 (2013)
An enantioselective asymmetric total synthesis of (+)-biotin (1) via the Hoffmann-Roche lactone-thiolactone strategy has been accomplished from commercially available cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2). Strategic transformations include a cinchona alkaloid-based bifunctional thiourea mediated methanolytic desymmetrization of prochiral cyclic anhydride 3 to produce the enantiomerically enriched precursor of Roche lactone 5 and an improved introduction of the 4-carboxybutyl side chain at C-4 position of Roche thiolactone 6 via Grignard reaction.
SYSTEMS AND METHODS FOR DETECTION OF TARGET ANALYTES USING SELECTIVELY CLEAVABLE BONDS
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, (2021/09/10)
The invention described herein is directed to methods of isolation and detection of target analytes in a sample. The target analytes are coupled to analyte detection particles which comprise base particles having labels and affinity agents coupled thereto by linker arms. The linker arms form bonds with the labels and target analytes and are cleavable under different label and affinity cleavable conditions. Systems and methods for preparing and using the analyte detection particles are also disclosed.
METHOD FOR PRODUCING BIOTIN
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Paragraph 0067-0083, (2021/02/25)
To provide a production method for obtaining high-purity biotin at good yields.SOLUTION: A method for producing biotin includes a process in which a composition comprising biotin represented by the formula (I) is brought into contact with hydrosulfite salt, before the biotin is extracted.SELECTED DRAWING: None
Solution Dynamics of Hybrid Anderson-Evans Polyoxometalates
Salazar Marcano, David E.,Lentink, Sarah,Moussawi, Mhamad A.,Parac-Vogt, Tatjana N.
supporting information, p. 10215 - 10226 (2021/05/31)
Understanding the stability and speciation of metal-oxo clusters in solution is essential for many of their applications in different areas. In particular, hybrid organic-inorganic polyoxometalates (HPOMs) have been attracting increasing attention as they combine the complementary properties of organic ligands and metal-oxygen nanoclusters. Nevertheless, the speciation and solution behavior of HPOMs have been scarcely investigated. Hence, in this work, a series of HPOMs based on the archetypical Anderson-Evans structure, δ-[MnMo6O18{(OCH2)3C-R}2]3-, with different functional groups (R = -NH2, -CH3, -NHCOCH2Cl, -NCH(2-C5H4N) {pyridine; -Pyr}, and -NHCOC9H15N2OS {biotin; -Biot}) and countercations (tetrabutylammonium {TBA}, Li, Na, and K) were synthesized, and their solution behavior was studied in detail. In aqueous solutions, decomposition of HPOMs into the free organic ligand, [MoO4]2-, and free Mn3+ was observed over time and was shown to be highly dependent on the pH, temperature, and nature of the ligand functional group but largely independent of ionic strength or the nature of the countercation. Furthermore, hydrolysis of the amide and imine bonds often present in postfunctionalized HPOMs was also observed. Hence, HPOMs were shown to exhibit highly dynamic behavior in solution, which needs to be carefully considered when designing HPOMs, particularly for biological applications.
Preparation method for preparing d-biotin by removing N-benzyl by Lewis acid
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Paragraph 0019-0060, (2021/02/24)
The invention provides a preparation method for preparing d-biotin by removing N-benzyl by Lewis acid, which comprises the following steps: removing dibenzyl from a dibenzyl biotin solution and Lewisacid in an anhydrous organic solvent under the protection of inert gas by one-step reaction to obtain d-biotin with the total yield of 90% or above and the content of 99% or above, wherein the productmeets the European Pharmacopoeia EP10.0 standard.
