619-45-4Relevant articles and documents
Photosensitive self-assembled monolayers on gold: Photochemistry of surface-confined aryl azide and cyclopentadienylmanganese tricarbonyl
Wollman, Eric W.,Kang, Doris,Frisbie, C. Daniel,Lorkovic, Ivan M.,Wrighton, Mark S.
, p. 4395 - 4404 (1994)
Photosensitive self-assembled monolayers (SAMs) are prepared by the spontaneous reaction of di-11-(4-azidobenzoate)-1-undecyl disulfide, I, or 11-mercaptoundecylcyclopentadienylmanganese tricarbonyl, II, with polycrystalline Au. SAMs of I are photosensitive by virtue of a pendant aryl azide moiety (λmax = 270 nm, log ε = 4.2) which undergoes photoreaction with secondary amines to form Au-confined derivatives of 3-H azepine and hydrazine, while Au-II SAMs undergo photosubstitution of phosphine for CO. Au-I SAMs irradiated in the presence of various secondary amines were characterized by reflection absorption infrared spectroscopy (RAIRS), XPS, and cyclic voltammetry, and showed persistent attachment of approximately one monolayer of amine. Infrared spectroscopy was used to establish that primary photoproducts obtained upon irradiation of Au-I SAMs in diethylamine are nearly identical to primary photoproducts obtained upon irradiating an analog of I, methyl 4-azidobenzoate, in diethylamine solution. XPS analysis of Au-I SAMs before and after irradiation in the presence of secondary amines confirms loss of N2 from the Au-I SAM and incorporation of one nitrogen atom per surface-confined molecule. Most definitively, cyclic voltammetry of Au-I after irradiation in the presence of 2-ferrocenylethyl-2′,2′,2′-trifluoroethylamine, III, showed 3.3 × 10-10 mol cm-2 of surface-confined ferrocene. Positive ion SIMS spectra of Au-II irradiated in the presence of PPh2Et, PPh2(n-Pr), PPh2(CH2)11Fc, X, Fc = ferrocenyl, or PPh2(CH2)2(CF2)5CF 3, XI, show that introduction of the phosphine onto the surface occurs upon near-UV irradiation. Importantly, the surface photochemistry of I and II allows the high lateral resolution patterning of Au surfaces and Au microstructures with a variety of molecular reagents. SIMS maps for vinyl ferrocenium (m/z 212) or F- (m/z 19) of flat Au-II substrates irradiated through a Cr-on-glass mask in the presence of X or XI demonstrate photochemical patterning at a lateral resolution of 2H5OH)2NH.
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Schwartz,Paruta
, p. 252,253-255 (1976)
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Carboxyl Methyltransferase Catalysed Formation of Mono- and Dimethyl Esters under Aqueous Conditions: Application in Cascade Biocatalysis
Ashbrook, Chloe,Carnell, Andrew J.,Goulding, Ellie,Hatton, Harry,Johnson, James R.,Kershaw, Neil M.,McCue, Hannah V.,Rigden, Daniel J.,Ward, Lucy C.
supporting information, (2022/02/21)
Carboxyl methyltransferase (CMT) enzymes catalyse the biomethylation of carboxylic acids under aqueous conditions and have potential for use in synthetic enzyme cascades. Herein we report that the enzyme FtpM from Aspergillus fumigatus can methylate a broad range of aromatic mono- and dicarboxylic acids in good to excellent conversions. The enzyme shows high regioselectivity on its natural substrate fumaryl-l-tyrosine, trans, trans-muconic acid and a number of the dicarboxylic acids tested. Dicarboxylic acids are generally better substrates than monocarboxylic acids, although some substituents are able to compensate for the absence of a second acid group. For dicarboxylic acids, the second methylation shows strong pH dependency with an optimum at pH 5.5–6. Potential for application in industrial biotechnology was demonstrated in a cascade for the production of a bioplastics precursor (FDME) from bioderived 5-hydroxymethylfurfural (HMF).
Method for synthesizing heteroatom- substituted aromatic compound from styrene compound
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Paragraph 0166-0168, (2021/02/06)
The invention discloses a method for synthesizing a heteroatom-substituted aromatic compound from a styrene compound, which comprises the following steps of: mixing a styrene compound with a general formula (I) and a heteroatom-containing compound with a general formula (II), and reacting in the presence of an acid additive and an organic solvent to obtain a heteroatom-substituted compound with ageneral formula (III). According to the synthesis method disclosed by the invention, a large amount of styrene compounds are used as raw materials and react to generate aromatic amine or phenol compounds under the action of no metal catalysis; and compared with the traditional aromatic amine and phenol synthesis method, the method has the advantages of high yield, simple conditions, low waste discharge amount, no metal participation, simple reaction equipment, easiness in industrial production and the like.
Optimizing the structure of (salicylideneamino)benzoic acids: Towards selective antifungal and anti-staphylococcal agents
Krátky, Martin,Kone?ná, Klára,Broke?ová, Kate?ina,Maixnerová, Jana,Trejtnar, Franti?ek,Vin?ová, Jarmila
, (2021/02/03)
An increasing resistance of human pathogenic bacteria and fungi has become a global health problem. Based on previous reports of 4-(salicylideneamino)benzoic acids, we designed, synthesised and evaluated their me-too analogues as potential antimicrobial agents. Forty imines derived from substituted salicylaldehydes and aminobenzoic acids, 4-aminobenzoic acid esters and 4-amino-N-phenylbenzamide were designed using molecular hybridization and prodrug strategies. The target compounds were synthesized with high yields and characterized by spectral methods. They were investigated against a panel of Gram-positive and Gram-negative bacteria, mycobacteria, yeasts and moulds. The most active imines were tested to determine their cytotoxicity and selectivity in HepG2 cells. Dihalogenosalicylaldehydes-based derivatives showed potent broad-spectrum antimicrobial properties, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 7.81 μM) and Enterococcus faecalis (MIC of ≥15.62 μM), yeasts (MIC from 7.81 μM) and Trichophyton interdigitale mould (MIC of ≥3.90 μM). Methyl 4-[(2-hydroxy-3,5-diiodobenzylidene)amino]benzoate 4h exhibited excellent in vitro activity along with low toxicity to mammalian cells. This compound is selective for staphylococci, Candida spp. and Trichophyton interdigitale. In addition, this imine was evaluated as a potential inhibitor of Gram-positive biofilms. The successful approach used provided some promising derivatives with more advantageous properties than the parent 4-(salicylideneamino)benzoic acids.