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UFS busy with exciting research into flavours and fragrances

11 July 2022 | Story Andre Damons | Photo Supplied

Prof Martie Smith and Prof Drik Opperman — Prof Martie Smit and Prof Dirk Opperman in the Department of Microbiology and Biochemistry filed a patent entitled “Process for the chemical modification of alkanes, fatty acids and fatty alcohols”.

Flavours and fragrances have a wide application in the food, feed, cosmetic, chemical and pharmaceutical sectors. Many flavour compounds are still produced via chemical synthesis or via extraction from plant or animal sources. However, there is increasing interest in their bio-production or the use of flavour compounds of (micro) biological origin.

One reason for this shift is that chemical synthesis often uses environmentally unfriendly processes. Chemical synthesis usually also produces racemic mixtures with the second enantiomer, mirror image of the looked-for compound, often having undesirable organoleptic properties. Furthermore, the consumer has developed a “chemophobia”-attitude towards synthetic chemical compounds, especially when related to food and home-care products. This applies even to nature-identical compounds – products that occur in nature but are produced via a non-natural chemical process. Products produced with the use of enzymes or microbes from “natural” substrates can be labelled “natural”. The flavour and fragrance industry thus pay higher prices for such products labelled as “natural”.

The invention

A University of the Free State (UFS) team, led by Prof Martie Smit and Prof Dirk Opperman in the Department of Microbiology and Biochemistry are conducting exciting research in this area. They filed a patent entitled “Process for the chemical modification of alkanes, fatty acids and fatty alcohols”.

The invention relates to a process for the enzymatic in-chain hydroxylation of C12 to C16 fatty acids, alcohols, and alkanes. Hydroxylation of C12 fatty acid and alcohol provides routes for the synthesis of “natural” δ-dodecalactone. The advantage of these routes is that they do not rely on massoia lactones. Massoia lactones are derived from the bark of Massoia trees which grow in Indonesia. Harvesting of the bark kills the trees.

The cytochrome P450 enzymes (P450s) claimed in this patent are to the inventors’ knowledge the most regioselective enzymes described thus far that can be used for the synthesis of δ-dodecalactone from lauric acid or 1-dodecanol. The approach that the technology takes is to claim cytochrome P450 enzymes that share 70 % amino acid identity to a set of selected P450s for the regioselective hydroxylation of lauric acid and 1-dodecanol to synthesise δ-dodecalactone.

Still in early stage

The current state of development is early stage with the technology only demonstrated in the laboratory on a small scale (100-200 ml). Before the technology can be commercialised the team would need to further improve the regioselectivity and stability of the P450s and proof that the reactions can be scaled up in bioreactors. The technology will probably be delivered as an enzyme (amino acid sequence) with the desired properties.

There are other research groups working on a synthetic biology approach for the de novo synthesis of δ-dodecalactone from glucose by genetically engineered microbes. It is still unclear how such a process will compare in terms of product yields, economics and environmental impact with the processes proposed by the UFS patent.

If the team had to partner with a commercial company, their first choice would be to work with an established flavour and fragrance company. Another possibility would be the small French flavour and fragrance company that Dr Alizé Pennec, the post-doc and co-inventor who initially discovered the unique P450 activity, is working for.

Please view the videos for more information on patents.

The Vice-Rector: Research and Internationalisation has released two new calls for applications for funding. Academic staff and researchers are encouraged to submit applications for these funds. At this stage we are not accepting projects from Research Fellows.

The two funds are:

1. The Industrial Engagement Fund

2. The Intellectual Property Commercialisation Fund

Each fund has its own guidelines and application process. The guidelines are attached. The applications must be filled in on RIMS.

The RIMS application forms can be found through this link

For more information please click the documents below:

IP Commercialisation Fund Concept Note

The UFS Industry Engagement Fund Concept Note

News Archive

UFS boasts with most advanced chemical research apparatus in Africa

2005-11-23

Celebrating the inauguration of the NMR were from the left Prof Frederick Fourie (Rector and Vice-Chancellor of the UFS), Dr Detlef Müller (Development Scientist and Manager: Africa and Asia of Bruker in Germany, the supplier of the NMR), Prof Jannie Swarts (head of the head of the Division Physical Chemistry at the UFS) and Prof Herman van Schalkwyk (Dean: Faculty of Natural and Agricultural Sciences at the UFS). Photo: Lacea Loader

UFS boasts with most advanced chemical research apparatus in Africa

The University of the Free State’s (UFS) Department of Chemistry now boasts with some of the most advanced chemical research apparatus in Africa after the latest addition, a nuclear magnetic resonance (NMR) spectrometer, was inaugurated today by the Rector and Vice-Chancellor, Prof Frederick Fourie. The NMR is used to analyse molecular structures.

Last month the Department of Chemistry celebrated the installation of the most advanced single crystal X-ray diffractometer in Africa. The diffractometer provides an indispensable technique to investigate among others the solid state of compounds for medicinal application.

“Three years ago the UFS executive management realised that, if we want to build a university of excellence, we should invest in research. We started to think strategically about chemistry and decided to bring the apparatus at the Department of Chemistry on a more competitive standard. Strategic partnerships were therefore secured with companies like Sasol,” said Prof Fourie during the inauguration ceremony.

“The installation of the NMR symbolises the ability of the UFS to turn academic areas around. I hope that this is the beginning of a decade of excellence for chemistry at the UFS,” said Prof Fourie.

”The catalogue value of the Bruker 600 MHz NMR is approximately R11 million. With such an advanced apparatus we are now able to train much more post-graduate students,“ said Prof Jannie Swarts, head of the Division Physical Chemistry at the UFS.

”The NMR is the flagship apparatus of the UFS Department of Chemistry that enables chemists to look at compounds more easily at a molecular level. Research in chemistry is critically dependent on NMR, which is a technique that can determine the composition of reactants and products in complicated chemical reactions, with direct application is most focus areas in chemistry,“ said Prof Swarts.

”Parts of the spectrometer consists of non-commercial items that were specifically designed for the UFS Department of Chemistry to allow the study of unique interactions in e.g. rhodium and platinum compounds,” said Prof Swarts.

According to Prof Swarts the NMR enables chemists to conduct investigations on the following:

To evaluate for example the complex behaviour of DNA in proteins as well as the analysis of illegal drugs sometimes used by athletes.
It provides an indispensable technique to investigate compounds for medicinal application for example in breast, prostate and related bone cancer identification and therapy, which are currently synthesised in the Department of Chemistry.
It can also be applied to the area of homogeneous catalysis where new and improved compounds for industrial application are synthesized and characterised, whereby Sasol and even the international petrochemical industry could benefit. This analytical capacity is highly rated, especially in the current climate of increased oil prices.
The NMR can detect and identify small concentrations of impurities in feed streams in the petrochemical industry, e.g. at Sasol and also the international petrochemical industry. These minute amounts of impurities can result in metal catalyst deactivation or decomposition and can cause million of rands worth in product losses.
It is indispensable for studying the complexity of samples that is non-crystalline. These materials represent the vast majority of chemical compounds such as solvents, gasoline, cooking oil, cleaning agents and colorants as examples.

According to Prof Swarts the general medical technique of MRI (magnetic resonance imaging) in use at larger hospitals, is based on NMR technology.

”The NMR apparatus enabled the Department of Chemistry to characterise complex molecules that were synthesised for the multi-national company, FARMOFS-PAREXEL, and to negotiate research agreements with overseas universities,” said Prof Swarts.

Media release
Issued by: Lacea Loader
Media Representative
Tel: (051) 401-2584
Cell: 083 645 2454
E-mail: loaderl.stg@mail.uovs.ac.za
22 November 2005

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