Carbosynth LTD

Compton, United Kingdom

Carbosynth LTD

Compton, United Kingdom

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Agoston K.,Institute of Organic Chemistry | Agoston K.,Carbosynth LTD | Watt G.M.,Carbosynth LTD | Fugedi P.,Institute of Organic Chemistry
Tetrahedron Letters | Year: 2015

Abstract A monosaccharide unit was synthesized bearing four different temporary protecting groups. The protecting groups used (Fmoc carbonate, NAP ether, levulinoyl and chloroacetyl esters) and the anomeric thio-glycoside form a new set of orthogonal protecting groups. The orthogonality of these groups has been demonstrated on the monosaccharide scaffold. © 2015 Elsevier Ltd.


Liu Z.,University of Oxford | Yoshihara A.,Kagawa University | Wormald M.R.,University of Oxford | Jenkinson S.F.,University of Oxford | And 3 more authors.
Organic Letters | Year: 2014

Addition of human milk oligosaccharides (HMO) to baby foods may protect infants from disease. As many simple HMOs are fucosylated this is likely to increase the demand for l-fucose as a synthetic building block. Any chemical synthesis must be cheap to compete with a biotechnological process. Acetonide is the only protecting group we have used in this new synthesis of l-fucose from vitamin C in 27% overall yield (purification by recrystallization; no chromatography required in the entire sequence). © 2014 American Chemical Society.


Agoston K.,Hungarian Academy of Sciences | Streicher H.,Carbosynth Ltd | Fugedi P.,Hungarian Academy of Sciences
Tetrahedron Asymmetry | Year: 2016

A large number of different sets of orthogonal protecting groups have been developed and used in carbohydrate chemistry over the last decade. These orthogonal sets are collected and summarized in this report. The ‘artificial’ classification of this review is based on the number of the protecting groups involved in the examined set. © 2016 Elsevier Ltd


Desmet T.,Ghent University | Soetaert W.,Ghent University | Bojarova P.,Academy of Sciences of the Czech Republic | Karen V.,Academy of Sciences of the Czech Republic | And 3 more authors.
Chemistry - A European Journal | Year: 2012

Glycosylation can significantly improve the physicochemical and biological properties of small molecules like vitamins, antibiotics, flavors, and fragrances. The chemical synthesis of glycosides is, however, far from trivial and involves multistep routes that generate lots of waste. In this review, biocatalytic alternatives are presented that offer both stricter specificities and higher yields. The advantages and disadvantages of different enzyme classes are discussed and illustrated with a number of recent examples. Progress in the field of enzyme engineering and screening are expected to result in new applications of biocatalytic glycosylation reactions in various industrial sectors. Industrial and academic research on enzymatic glycosylation of small molecules is discussed in this Review article. Biocatalytic alternatives are presented that offer both stricter specificities and higher yields. The advantages and disadvantages of different enzyme classes are discussed and illustrated with a number of recent examples. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Laurenson J.A.B.,University of Strathclyde | Laurenson J.A.B.,Carbosynth Ltd. | Parkinson J.A.,University of Strathclyde | Percy J.M.,University of Strathclyde | And 2 more authors.
Beilstein Journal of Organic Chemistry | Year: 2013

Esters of crotonic acid were brominated on a multigramme scale using a free radical procedure. A phase transfer catalysed fluorination transformed these species to the 4-fluorobut-2E-enoates reproducibly and at scale (48-53%, ca. 300 mmol). Asymmetric dihydroxylation reactions were then used to transform the butenoate, ultimately into all four diastereoisomers of a versatile fluorinated C4 building block at high enantiomeric-enrichment. The (DHQ) 2AQN and (DHQD)2AQN ligands described by Sharpless were the most effective. The development and optimisation of a new and facile method for the determination of ee is also described; 19F{1H} spectra recorded in d-chloroform/diisopropyl tartrate showed distinct baseline separated signals for different enantiomers. © 2013 Laurenson et al; licensee Beilstein-Institut.


Agoston K.,Institute of Organic Chemistry | Agoston K.,Carbosynth LTD | Agoston A.,Laboratory Computer LTD | Dorgan C.R.,Carbosynth LTD | Fugedi P.,Institute of Organic Chemistry
Carbohydrate Research | Year: 2015

A new test was elaborated to identify a new set of orthogonal protecting groups. With the developed method eight different protecting groups were tested under various deprotection conditions and the complex reaction mixtures were analysed by HPLC. The developed method allows for quick identification of orthogonality using simple model structures. © 2015 Elsevier Ltd. All rights reserved.


Grant
Agency: European Commission | Branch: H2020 | Program: BBI-RIA | Phase: BBI.VC3.R6 | Award Amount: 5.96M | Year: 2015

This project aims to develop new processes and solve bottlenecks in the fermentative production of biosurfactants and specialty carbohydrates. Specifically, the project targets the development of innovative fermentation processes to produce the following compounds: 1. Glycolipid biosurfactants. The project targets four distinct classes of biosurfactants, specifically rhamnolipids, sophorolipids, xylolipids and mannosylerythritol-lipids with a wide range of application fields. 2. Specialty carbohydrates. Specifically, the project targets sialylated oligosaccharides, a class of very complex Human Milk Oligosaccharides that find application as a neutraceutical, pharmaceutical and cosmetic ingredient. For both product lines, microbial producer strains will be developed through metabolic engineering. The fermentation process and down-stream processing will be developed and optimized in order to obtain an industrial process. Second generation technology based on lignocellulosic substrates will also be developed. Sufficient amounts of the new products will be produced for application testing, in order to evaluate their market potential in a wide range of application fields. The technical, economic, environmental and social sustainability of the process over the whole value chain from biomass to product application will also be assessed, with an emphasis on identifying and addressing the bottlenecks in the innovation chain. A valorisation plan will be drafted to complete the innovation process. The project consortium has all the required players to obtain the expected impact: RTOs to address the research challenges in this project, an open innovation pilot plant to optimize and scale up the new processes, three biotech SMEs and three large industries to ensure the exploitation of the project results. In addition, two user groups (one for each product line) consisting of end-user companies are involved in the project.


Grant
Agency: European Commission | Branch: FP7 | Program: CP-IP | Phase: KBBE.2013.3.3-01 | Award Amount: 6.22M | Year: 2013

IB2Market aims to bring industrial biotechnology from the research lab to the market and to solve the bottle-necks in industrialisation. Specifically, the project targets the development and scale-up of new industrial biotechnology processes that have recently been developed to produce the following compounds: 1. Biosurfactants, tensioactive ingredients with a wide range of applications. Specifically, the project targets bola-sophorolipids, a completely new type of biosurfactants. 2. Specialty carbohydrates, mainly for pharmaceutical and cosmetic applications. Specifically, the project targets L-fucose and fucosylated oligosaccharides that are very difficult to produce through extraction or chemical synthesis. For both product lines, the fermentation process and down-stream processing will be optimised and scaled up to 15.000 litre scale. Sufficient amounts of product will be produced for application testing and exploratory marketing, in order to identify the most interesting market segments. The technical, economic and environmental sustainability of the process from biomass to product application will also be assessed, with particular emphasis on identifying and solving the bottlenecks in the innovation chain. A valorisation plan will be drafted to complete the innovation chain. The project will result in the industrialisation and commercialisation of the developed products and processes. The project consortium has all the required players to move a process from lab scale to industrialisation: an open innovation pilot plant (Bio Base Europe Pilot Plant), a biotech start-up company (Inbiose), marketing companies for surfactants (EOC-surfactants) and specialty carbohydrates (Carbosynth), the RTD organisation that developed the processes at lab-scale (Ghent University), an application developer (Innovhub) and service-providing SMEs (Nova institute and BCNP consultants).


Grant
Agency: European Commission | Branch: FP7 | Program: CP-FP | Phase: KBBE.2010.3.3-01 | Award Amount: 3.73M | Year: 2010

This project aims to develop novel biocatalysts for the production of glycosides (NOVOSIDES). Glycosylated compounds have a wide range of applications, but very few enzymes are able to glycosylate small organic molecules cost-efficiently at the industrial scale. Therefore, glycosylation reactions catalysed by transglycosidases, glycoside phosphorylases and glycoside hydrolases will be explored in more detail. These enzymes catalyze the transfer a glycosyl group from a cheap and readily available donor substrate to a variety of acceptors. To exploit their full potential, the enzymes specificity and stability against high temperatures and the presence of organic co-solvents will be optimised by means of directed evolution. A large and diverse collection of enzymes will first be established by screening in natural environments and by the mining of public (meta)genome databases. The enzyme collection will then be screened for activity on a variety of representative acceptors from different chemical classes. This will allow the identification of the most promising enzymes for optimisation through semi-rational and random mutagenesis. The high-throughput screening of natural and variant enzymes will be performed with newly developed fluorescent probes, that allow fast and accurate measurements of carbohydrate-active enzymes in a direct and non-destructive assay. To achieve these ambitious goals, a complementary consortium of academia and industry has been formed that covers the whole range of required expertises. The economical potential of our technology will be demonstrated by the development and scale-up of selected glycosylation reactions at pilot-plant facilities. The produced glycosides will be actively marketed to potential end-users to promote the valorisation of the projects results and to initiate future collaborations on novel target compounds.


PubMed | Hungary; Carbosynth LTD, Laboratory Computer LTD, Institute of Organic Chemistry and Carbosynth LTD
Type: | Journal: Carbohydrate research | Year: 2015

A new test was elaborated to identify a new set of orthogonal protecting groups. With the developed method eight different protecting groups were tested under various deprotection conditions and the complex reaction mixtures were analysed by HPLC. The developed method allows for quick identification of orthogonality using simple model structures.

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