Search results for "hydroxylation"

Collagen overglycosylation: a biochemical feature that may contribute to bone quality.

2005

Skeletal ability to resist mechanical stress is determined by bone amount and quality, which relies on macro- and micro-architecture, turnover, bone matrix, and mineralisation; the role of collagen has not been clearly elucidated. Numerous post-translational steps are involved in collagen type I biosynthesis, including residue hydroxylation and glycosylation catalysed by enzymes that work until the protein folds forming the triple helix; therefore, folding rate regulates these processes. Overglycosylated hydroxylysines are poor substrates for epsilon-amino group deamination which initiates cross-link formation. Three clinical conditions associated with fractures may relate collagen overglyc…

Effect of the cytochrome P-450 inactivator 1-aminobenzotriazole on the metabolism of chlortoluron and isoproturon in wheat

1987

Abstract Roots of young wheat plants ( Triticum aestivum cv Clement) were treated with [ 14 C]chlortoluron or [ 14 C]isoproturon alone or mixed with 1-aminobenzotriazole (ABT), a mechanism-based inactivator of cytochrome P -450 monooxygenases. Radioactivity extracted from shoots slightly decreased during periods of metabolism, this decrease being reduced by ABT in the case of isoproturon. ABT strongly inhibited the metabolism of both herbicides. Accumulation of metabolites was generally depressed in the presence of ABT; however, levels of the free N -monodemethylated derivatives were little or not affected. It is concluded that ABT is a synergist of chlortoluron and isoproturon in wheat bec…

Reversible inhibition of C1Q release from guinea pig macrophages by 2,2'-dipyridyl: Evidence for a posttranslational hydroxylation step in the biosyn…

1978

A Selective Synthesis of Fluorinated Cispentacin Derivatives

2014

A facile selective method has been developed for the synthesis of new fluorine-containing cispentacin stereoisomers. Mono- and difluorinated cispentacin derivatives were synthetized from a bicyclic β-lactam in five or six steps involving a regio- and stereoselective hydroxylation through iodooxazoline formation, followed by deoxygenation by fluorination. Starting from an enantiomerically pure bicyclic β-lactam obtained by enzymatic resolution of the racemic compound, an enantiodivergent procedure allowed the preparation of both dextro- and levorotatory difluorinated cispentacins.

Kinetic properties of hexameric tyrosinase from the crustacean Palinurus elephas.

2008

Tyrosinases catalyze hydroxylation of monophenols to o-diphenols and their subsequent oxidation to o-quinones, whereas catecholoxidases catalyze only the latter reaction. Both enzymes occur in all organisms and are Type 3 copper proteins that perform the first steps of melanin formation. In arthropods, they play an essential role in the sclerotization of the exoskeleton. Very few phenoloxidases are characterized structurally or kinetically and the existence of an actual tyrosinase activity has not been demonstrated in most cases. Here we present for the first time a complete kinetic characterization of a tyrosinase from a crustacean (Palinurus elephas) including the influence of inhibitors.…

Hydroxylation and conjugation of phenol by the frog Rana temporaria.

1985

1. Frogs injected with phenol excrete 67–95% of dose in 15h; 32–87% of dose are metabolites.2. Metabolites identified were phenyl sulphate (15–44% of dose), phenyl glucuronide (10–25% of dose), catechol sulphate (up to 7% of dose), quinol sulphate (1–25% of dose), resorcinol and catechol (traces).

Increased 2-Hydroxylation of Estrogen in Women with a Family History of Osteoporosis

2005

Recent studies indicate that women with predominant estrogen metabolism through the 2-hydroxyl (inactive) pathway have lower bone mineral density (BMD) compared with those with predominant 16alpha-hydroxylation (active). Although many factors have been identified to affect estrogen metabolism, the role of a family history of osteoporosis remains unknown. The objective of this study was to investigate the influence of family history of osteoporosis and other clinical factors on estrogen hydroxylation. This was a cross-sectional study conducted in a university-based research center from May 2002 to February 2004. The participants included 175 otherwise healthy postmenopausal women at least 1 …

Multigram Scale Enzymatic Synthesis of (R)-1-(4′-Hydroxyphenyl)ethanol Using Vanillyl Alcohol Oxidase

2018

The enantioselective oxyfunctionalisation of C−H bonds is a highly interesting reaction, as it provides access to chiral alcohols that are important pharmaceutical building blocks. However, it is hard to achieve using traditional methods. One way in which it can be achieved is through the action of oxidative enzymes. Although many reports of the oxyfunctionalisation capabilities of enzymes at an analytical scale have been published, reports on the use of enzymes to achieve oxyfunctionalisation on a synthetically relevant scale are fewer. Here, we describe the scale-up of the conversion of 4-ethylphenol to (R)-1-(4′-hydroxyphenyl)ethanol using the flavin-dependent enzyme vanillyl alcohol oxi…

Stereoselective synthesis and application of tridentate aminodiols derived from (+)-pulegone

2016

Abstract A library of tridentate aminodiols, derived from naturally occurring (R)-(+)-pulegone, was synthesized and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The reduction of pulegone furnished pulegol, which was transformed into allylic trichloroacetamide via Overman rearrangement of the corresponding trichloroacetimidate. The protected enamine was subjected to dihydroxylation with OsO4/NMO system resulting in a 1:1 mixture of (1R,2R,4R)- and (1S,2S,4R)-aminodiol diastereomers. After the removal of the trichloroacetyl protecting groups, the obtained primary aminodiols were transformed into secondary ones. The regioselectivity of the ring closure of the N-b…

Xanthine oxidase catalyzes the oxidation of retinol.

2007

In mammals, xanthine oxidase (E.C. 1.17.3.2) catalyzes the hydroxylation of a wide variety of heterocyclic substrates such as purines, pyrimidines, and pterins, in addition to aldehydes [1] as all-trans-retinaldehyde [2-5]. Here, we show that buttermilk xanthine oxidase was capable to oxidizing all-trans-retinol (t-ROL) to all-trans-retinaldehyde (t-RAL) that was successively oxidized to all-trans-retinoic acid (t-RA). A rise in the enzyme activity, when t-ROL-CRBP complex was assayed, with respect to the free t-ROL, was observed. Furthermore, treatment of the enzyme with Na2S and glutathione resulted in a significant increment in catalytic activity toward t-ROL and t-RAL, due to the recons…