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.

Journal Details

This article was published in the following journal.

Name: Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Pages: 10355-61


DeepDyve research library

PubMed Articles [15519 Associated PubMed Articles listed on BioPortfolio]

BioJava-ModFinder: identification of protein modifications in 3D structures from the Protein Data Bank.

We developed a new software tool, BioJava-ModFinder, for identifying protein modifications observed in 3D structures archived in the Protein Data Bank (PDB). Information on more than 400 types of prot...

Dual gold and photoredox catalysed C-H activation of arenes for aryl-aryl cross couplings.

A mild and fully catalytic aryl-aryl cross coupling via gold-catalysed C-H activation has been achieved by merging gold and photoredox catalysis. The procedure is free of stoichiometric oxidants and a...

Borinic acid Catalysed Hydrosilanes Reduction of Tertiary Amides: A Mild and Chemoselective Synthesis of Amines.

A reduction of various aryl, alkyl and α,β-unsaturated amides with phenylsilane catalysed by a borinic acid is reported. The reaction carried out under unprecedented very mild conditions and led to ...

Enzymatic behavior of laccase following interaction with γ-CD and immobilization into PCL nanofibers.

This study examines the effects of CD use on enzymatic activity, following enzyme immobilization into nanofibers. There is almost no research available on the change in enzyme activity following inter...

Synthesis of amine-functionalized Fe3O4@C nanoparticles for laccase immobilization.

Amine-functionalized Fe3O4@C nanoparticles with an average diameter of 266nm have been successfully synthesized by a solvothermal reduction method. The structure, morphology and properties of the Fe3O...

Clinical Trials [3538 Associated Clinical Trials listed on BioPortfolio]

Optimize RV Selective Site Pacing Clinical Trial

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...

Brain Imaging Techniques That Predict Antidepressant Responsiveness

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...

Staging Accuracy of a Selective Lymphadenectomy Strategy in Early Stage NSCLC

Systemic mediastinal lymphadenectomy is deemed indispensable in lung cancer surgery for accurate staging and complete resection. However, extensive lymphadenectomy in patients without noda...

What Treatment Works for Children With Selective Mutism?

The purpose of this pilot study is to explore the outcome of a manual based treatment for children with Selective Mutism

The Natural History of Atopic Disease in Thai Children and Association With Atopic March

Atopic dermatitis(AD) is one of manifestation in atopic march. The prevalence of AD is increased. In 1998, the investigators found the prevalence of AD about 15 % in Thailand. AD is diagno...

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.

Quick Search

DeepDyve research library

Searches Linking to this Article