The crystal structures are described of N-(n-heptyl)-d-gluconamide (1) [space group P1, a = 5.183(7), b = 16.18(1), c = 4.803(5) Å, α = 94.2(1)°, β = 96.1(1)°, γ = 99.0(1)°] and of N-(n-decyl)-d-gluconamide (2) [space group P21, a = 5.255(2), b = 35.97(1), c = 4.807(2) Å, β = 94.81(3)°],...

N-Octylamides of diastereomeric gluconic and gulonic acids form molecular aggregates of extremely different curvature, namely helical micellar rods with a diameter of 4 nm and planar bilayers. In the crystal structure of the gulonamide compound, symmetric “tail-to-tail” bilayer sheets are obse...

The crystal structure of the title compound [5; space group P21; a = 8.375(5), b = 51.52(2), c = 5.6473(3) Å; β = 89.64(4)°] was determined by X-ray diffraction methods and refined to R = 0.107. There are two molecules in the asymmetric unit, which adopt nearly identical conformations. Each mo...

The crystal structure of N-(n-octyl)-D-gluconamide (space group P21, a = 5.252(1), b = 32.426(9), c = 4.805(1)Å, β = 94.96(5)°) was determined by X-ray diffraction methods and refined to R = 0.046. The molecules are V-shaped and occur in an all-trans conformation for both the aliphatic and D-...

N-(n-Octyl)-6-deoxy-d-gluconamide crystallizes in the orthorhombic space group P212121, with a = 5.4524(5), b = 16.662(3), and c = 36.897(5) Å. The structure was determined by X-ray diffraction and refined to R = 9.2%. The asymmetric crystal unit contains two molecules (A,B) with significantly d...

This study was aimed to evaluate the fate of D3G, 3-ADON, and 15-ADON during various processing steps (milling, fermentation, baking and cooking with water) of different cereal-based products, as well as the co-occurrence of culmorin (CUL) and its derivatives (15-Hydroxy-CUL and 5-Hydroxy-CUL. S...

Microbial enantioselective hydrolysis of diethyl-3-hydroxyglutarate afforded (S)-ethyl hydrogen-3-hydroxyglutarate, which was transformed into (R)-4-amino-3-hydroxybutyric acid and L-carnitine, via a Curtius and Hunsdiecker rearrangement, respectively.

Biocatalytic asymmetrizations of diethyl 3-hydroxyglutarate furnish a route to the enantiomers of ethyl 4-cyano-3-hydroxybutanoate. The enantiopreference of different enzymes has been established by chiral chromatography. Conclusive evidence for absolute configurations has been provided by X-ray...

Optically pure ethyl (S)-3-hydroxyglutarate [(S)-3-EHG] is used as a key precursor for synthesis of a variety of pharmaceutically important compounds. In this work, we established an efficient procedure for enantioselectively hydrolyzing diethyl 3-hydroxyglutarate (3-DHG) to optically active (S)...

Chiral phosphoric acid-catalyzed enantioselective Friedel–Crafts reaction of indoles with ethyl glyoxylate imines was developed. With 10 mol % of the catalyst, the Friedel–Crafts reactions between a wide range of indoles and imines have been carried out, affording optically active (3-indolyl)g...

Treatment of 1-hexadecyloxy-2,3-epoxypropane ot its derivatives, 1-chloro-3-hexadecyloxy-2-propanol and 2-hydroxy-3-hexadecyloxy-propyl p-toluensulfonate, with N-alkyl trifluroacetamides sodium salt gave 3-alkyl-oxazolidin-2-ones in good yields. The in situ formed alkoxy anion is believed to att...

A high pressure flow-mixing isothermal microcalorimeter was used to determine molar excess enthalpies of six binary systems for 2,4-pentanedione + (1-butanol, + 2-methyl-1-propanol, + 1-pentanol, + 1-heptane, + ethyl acetate, and + water) at T = 298.15, 313.15, and 328.15 K and p = 0.1 and 10.0 ...

Densities, refractive indices and speeds of sound at 298.15, 303.15, and 308.15 K are reported for the binary mixtures ethyl acetate + 2-butanol and ethyl acetate + 3-methyl-1-butanol. Isobaric vapor–liquid equilibrium data at 101.3 kPa were determined for the ethyl acetate + 3-methyl-1-butanol...

Densities of the binary liquid mixtures of 2-ethyl-1-butanol + dibutyl ether (DBE) or ethylene glycol mono butyl ether (EGMBE), 2-methyl-1-butanol + DBE, have been measured as a function of the composition at temperature range of 293.15 to 313.15 K and atmospheric pressure. The measurements have...

The densities of binary mixtures of ethyl acrylate with 1-butanol, 2-butanol, 2-methyl-1-propanol, and 2-methyl-2-propanol, including those of pure liquids, over the entire composition range were measured at temperatures (288.15, 293.15, 298.15, 303.15, 308.15, 313.15, and 318.15) K and atmosphe...

Treatment of phenylenediamines with methyl trimethoxyacetate led to the formation of 3-methoxy-quinoxalin-2-ones with the assistance of lanthanide-based Lewis acids.

2-(2-Cyano-1-ethylthioethenyl)pyrroles easy exchange their ethylthio group for hydroxyl (NaOH, H2O–methanol, 40–45 °C, 1 h) to give 2-(2-cyano-1-hydroxyethenyl)pyrroles, a new family of stable enols, in 50–94% yields. The vinylic nucleophilic substitution proceeds at the double bond of both ...

A new reagent for the routine identification of cysteine residues during protein sequencing is described. This method employs 3-bromopropylamine to alkylate cysteines in proteins after reduction with dithiothreitol. Upon sequencing of the protein on an Applied Biosystems 477A protein sequencer, ...

We have previously shown that 3-bromopropylamine offers several advantages over other alkylating reagents in the modification and subsequent identification of cysteine residues by protein sequencing. We describe here simple on-sequencer procedures for alkylating cysteines in proteins which emplo...

Various mammalian tissues contain membrane-bound amine oxidase termed semicarbazide-sensitive amine oxidase (SSAO). A variety of compounds has been identified as relatively selective SSAO inhibitors, but those inhibitors currently available also inhibit monoamine oxidase (MAO). In the present st...