The quest for new mild and selective modifications of natural structures: laccase-catalysed oxidation of ergot alkaloids leads to unexpected stereoselective C-4 hydroxylation.
Summary of "The quest for new mild and selective modifications of natural structures: laccase-catalysed oxidation of ergot alkaloids leads to unexpected stereoselective C-4 hydroxylation."
Laccase-catalysed oxidation of ergot alkaloids in the absence of chemical mediators allowed the unexpected isolation of the mono-hydroxylated derivatives of compounds 2-7. Structure determination by NMR techniques clearly indicated that hydroxylation took place at the C-4 benzylic position. Quite notably, the proposed protocol allowed, for the first time, functionalisation at the C-4 position of the ergoline skeleton. Depending on the absence or on the presence of a C-10 α-methoxy substituent, hydroxylation was either stereoselective (furnishing C-4α OH derivatives) or gave rise to a C-4α/C-4β OH mixture in a 2:1 ratio, respectively.
Istituto di Chimica del Riconoscimento Molecolare, C.N.R. Via Mario Bianco, 9, 20131, Milano (Italy), Fax: (+39) 02-28901239.
This article was published in the following journal.
Name: Chemistry (Weinheim an der Bergstrasse, Germany)
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22777708
- DOI: http://dx.doi.org/10.1002/chem.201201076
For the first time a laccase from Trametes versicolor was immobilized on a natural clinoptilolite with Si/Al=5 to obtain a biocatalyst for environmental applications. Immobilization procedures exploit...
The selective synthesis of 2,6-trans-tetrahydropyran derivatives employing the rhodium catalysed addition of organoboron reagents to dihydropyranone templates, derived from a zinc-catalysed hetero-Die...
The selective functionalisation of C-H bonds is a powerful strategy for the construction of organic molecules and the Rh(ii)-catalysed C-H insertion reaction is a particularly robust and useful tool f...
A non-symmetrical diboron reagent, B(pin)-B(dan), has been utilised in the Pd-catalysed borylation of aryl bromides and chlorides. Remarkably selective formation of aryl-B(dan) bonds is established. T...
The phosphate functionalized carbon dots (PCDs) with high bio-compatibility and low toxicity can be used as efficient additives for the construction of laccase/PCDs hybrid catalyst. A serials of exper...
The purpose of the Optimize RV study is to determine the long-term effect of selective site pacing. Selective site pacing refers to which area of the right ventricle the lead is placed. T...
Do functional brain changes occur during Venlafaxine ER (extended release) versus Fluoxetine treatment and do changes in selective structures, such as the amygdala, predict treatment respo...
The purpose of this pilot study is to explore the outcome of a manual based treatment for children with Selective Mutism
The purpose of the Optimize RV Follow-Up study is to determine the long-term effect of selective site pacing. Selective site pacing refers to which area of the right ventricle the lead is ...
Polyostotic fibrous dysplasia (PFD) is a sporadic disorder which affects multiple sites in the skeleton. The bone at these sites is rapidly resorbed and replaced by abnormal fibrous tissu...
Medical and Biotech [MESH] Definitions
Any of various enzymatically catalyzed post-translational modifications of PEPTIDES or PROTEINS in the cell of origin. These modifications include carboxylation; HYDROXYLATION; ACETYLATION; PHOSPHORYLATION; METHYLATION; GLYCOSYLATION; ubiquitination; oxidation; proteolysis; and crosslinking and result in changes in molecular weight and electrophoretic motility.
A species of gram-negative bacteria infecting DOGS, the natural hosts, and causing canine BRUCELLOSIS. It can also cause a mild infection in humans.
Patterns (real or mathematical) which look similar at different scales, for example the network of airways in the lung which shows similar branching patterns at progressively higher magnifications. Natural fractals are self-similar across a finite range of scales while mathematical fractals are the same across an infinite range. Many natural, including biological, structures are fractal (or fractal-like). Fractals are related to "chaos" (see NONLINEAR DYNAMICS) in that chaotic processes can produce fractal structures in nature, and appropriate representations of chaotic processes usually reveal self-similarity over time.
Mild to severe infections of the eye and its adjacent structures (adnexa) by adult or larval protozoan or metazoan parasites.
A species of gram-negative bacteria producing mild to severe ANAPLASMOSIS in SHEEP and GOATS, and mild or inapparent infections in DEER and CATTLE.