7031-23-4Relevant articles and documents
Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis
Adamson, Christopher,Kajino, Hidetoshi,Kanai, Motomu,Kawashima, Shigehiro A.,Yamatsugu, Kenzo
supporting information, p. 14976 - 14980 (2021/09/29)
Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.
Synthesis, spectral characterization, electrochemical properties and antimicrobial screening of sulfur containing acylferrocenes
Ili?, Danijela,Damljanovi?, Ivan,Stevanovi?, Dragana,Vuki?evi?, Mirjana,Radulovi?, Niko,Kahlenberg, Volker,Laus, Gerhard,Vuki?evi?, Rastko D.
scheme or table, p. 1863 - 1869 (2010/07/04)
Several known and eight new sulfur containing acylferrocenes of the general formula FcCO(CH2)nSR (where Fc = ferrocenyl, n = 1 or 2 and R = alkyl, 4-bromobenzyl or 2,6-dichlorobenzyl group) were synthesized in order to test their in vitro antimicrobial activity against 11 bacterial and three fungal/yeast strains. It has been shown that only four of the 14 ketones are completely inactive at the tested dose, while the activities of the other ones were noteworthy. All new compounds were well characterized by IR and NMR spectral data, and their electrochemical properties were investigated by cyclic voltammetry. The X-ray crystal structures of two representative ketones are also presented.
Studies on umami taste. Synthesis of new guanosine 5′-phosphate derivatives and their synergistic effect with monosodium glutamate
Cairoli, Paola,Morelli, Carlo F.,Speranza, Giovanna,Manitto, Paolo,Pieraccini, Stefano,Sironi, Maurizio
supporting information; experimental part, p. 1043 - 1050 (2009/05/08)
A number of N2-alkyl and N2-acyl derivatives of guanosine 5′-phosphate (GMP) have been synthesized and tested for their synergistic effect with monosodium L-glutamate (MSG), the prototypical substance imparting umami taste to savory-based foods. Capacities to enhance the taste intensity of MSG (γ values) were estimated through subjective comparisons of MSG/nucleotide mixtures in water with appropriate solutions of MSG alone. Assuming β = γ[nucleotide]/γ[IMP], β values of the N 2-substituted GMPs were found in the range 1.2-5.7. Such values appear to be related to the chain length of the substituent in the 2-position of the purine nucleus and dependent on the replacement of a CH2 group with an S atom and/or with an α-CO group. These findings indicate that the exocyclic NHR group of the guanine moiety is actively implicated in the synergism between GMP derivatives and MSG. Theoretical calculations suggest that an anti conformation is probably assumed by ribonucleotide molecules interacting with umami receptors.
