The isolation, structural determination, and total synthesis of terfestatin A, a novel auxin signaling inhibitor from Streptomyces sp.

Indole 3-acetic acid, a plant hormone auxin, regulates every aspects of plant growth and development. In the screening for specific inhibitors on auxin signaling using the transgenic Arabidopsis plant harboring the auxin-responsive reporter gene, terfestain A was found to be a novel inhibitor of auxin signaling from the culture of Streptomyces sp. F40. The structure of terfestatin A was determined to be p-terphenyl β-glucoside on the basis of spectroscopic analyses, chemical degradation, and total synthesis.     

The participation of the anion and alkyl substituent of diaryliodonium salts in photo‐initiated cationic polymerization reactions

The photo‐initiated cationic polymerization (PCP) of epoxides using diaryliodonium salt photoacid generators (PAGs) bearing alkyl groups and anions was investigated. The properties and reactivities of a series of iodonium salts containing various cations and anions were compared in the context of a PCP reaction. The products from the decomposition of the cations of these salts were analyzed using gas chromatography‐mass spectrometry (GC‐MS) spectra. The relationship between the molecular structure of the salts and their reaction mechanism in the PCP reaction was investigated. Based on the results of the investigation, it was concluded that the structures of the cations and anions of theiodonium salts affect the PCP reaction rate, which was controlled by the products from the diaryliodonium salts. As part of an additional investigation, the diaryliodonium salts‐epoxide materials were applied to 254 nm‐photo‐patterning. Copyright © 2006 John Wiley & Sons, Ltd.     

Catalytic reduction of nitrogen dioxide with propene in the presence and absence of oxygen over various metal oxides

Over metal oxides (SiO₂, ZrO₂, Al₂O₃, MgO, La₂O₃, and CaO) with-H values of metal oxide formation higher than 700 kJ/mol, C₃H₆ reacts with NO₂ in preference to O₂.     

Reaction of azole condensed quinoxaline N-oxides with acetic anhydride

The reaction of 7-chlorotetrazolo[1,5-α]quinoxaline 5-oxide 6a with acetic anhydride gave 7-chloro-5-(7-chlorotetrazolo[1,5-α]quinoxalin-4-yl)-4,5-dihydro-4-oxotetrazolo[1,5-α]quinoxaline 7a , while the reaction of 7-chloro-1,2,4-triazolo[4,3-α]quinoxaline 5-oxide 6b with acetic anhydride afforded 7-chloro-5-(7-chloro-1,2,4-triazolo[4,3-α]quinoxalin-4-yl)-4,5-dihydro-4-oxo-1,2,4-triazolo[4,3-α]quinoxaline 7b and 7-chloro-4,5-dihydro-4-oxo-1,2,4-triazolo[4,3-α]quinoxaline 8b . The reaction of compound 6a or 6b with acetic anhydride/acetic acid provided 7-chloro-4,5-dihydro-4-oxo-tetrazolo[1,5-α]quinoxaline 8a or compound 8b , respectively.     

Water-swellable polyelectrolyte microgels polymerized in an inverse microemulsion using a nonionic surfactant

A series of poly(dimethylacrylamide-co-2-acrylamido-2-methyl-1-propanesulfonic acid) microgels slightly crosslinked by methylene-bis-acrylamide (MBA) were polymerized in a novel inverse microemulsion polymerization (IMEP) system. To determine a suitable composition of the IMEP system, the phase diagram of a pseudoternary system was made. The pseudoternary polymerization system consisted of n-hexane, a nonionic surfactant (polyoxyethylene oleyl ether, C18En), and an aqueous monomer solution. Polymerization was performed in a single-phase reversed micelle solution. The reversed micelles were about 50 nm in diameter, as determined by FF-TEM. The viscometric characteristics of the polymers extracted from the IMEP system were studied in 3 mM sodium chloride aqueous solution. The intrinsic viscosity values for the noncrosslinked and crosslinked (0.1 mol% MBA was incorporated) samples were 25 and 7.4 dl/g, respectively. The overlap concentration (c*) of crosslinked polymer microgel occurred at c[eta] = 1 in the solvent. When the volume fraction (phi) of the microgel was 0.7, the value of the apparent yield stress of the microgel solution was observed. These results show that the microgel has a significant thickening effect above c* due to friction between the microgel particles. It is assumed that the microgels polymerized in a confined space retain the shape or size of the nanosized reactor with a diameter on the order of 50 nm.     

Synthesis and Odor Evaluation of Stereoisomers of Imine Derivatives in Roasted Spotted Shrimp

All possible stereoisomers of imine derivatives 1 – 4 , which have the characteristic roast odor of seafood, were synthesized. As a result of odor evaluation of all isomers, we found that each isomer has a different and characteristic odor of roasted seafood.     

Substituent effects on the tautomer ratios between the hydrazone imine and diazenyl enamine forms in side-chained quinoxalines

The 3-(arylhydrazono)methyl-2-oxo-1,2-dihydroquinoxalines 9–11 were synthesized by the reaction of the quinoxalines 6–8 with various p-substituted benzenediazonium salts. Compounds 9–11 showed the tautomeric equilibria between the hydrazone imine A and diazenyl enamine B forms in dimethyl sulfoxide media. The substituent effect on the tautomer ratios of A to B was studied by the nmr spectroscopy to clarify that the presence of the ester group R² on the hydrazone carbon and electron-donating p-substituent R¹ on the side chain benzene ring exhibited a tendency to increase the ratios of the tautomer A .