We have published an article in Chem. Sci. describing a cheap, low molecular weight glycosylation catalyst at loadings down to 0.1 mol%. Just 0.25 mg of thiouracil as catalyst was required to make 1 g of disaccharide product. The work evidences that the mechanism of activation is not through double H-bonding catalyst but rather by Brønsted acid/base catalysis. We also demonstrated application to the synthesis of glyconjugates and 1,1′-linked trehalose-type sugars (with relevance to TB studies).
Special congratulations to joint lead authors Gary and Avene; this paper contains key results from both their PhD theses and reflects a lot of hard work. Well done also to Mairead who contributed to the research as part of her final year BSc project. Ultimately a lot of hard work was put in by all the authors so well done too to Nathan and Ren, and thanks to Yannick for his work on special NMR experiments. Thanks also to our funders: SFI (SIRG and CDA awards supported Gary, Eoghan and Ren), IRC (PG Scholarship to Avene), and UCD (funding for Nathan).
The article is available as an open access article:
Chem Sci 2019, advance article. G A Bradshaw, A C Colgan, N P Allen, I Pongener, M B Boland, Y Ortin and E M McGarrigle* — Stereoselective organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings. DOI: 10.1039/C8SC02788A
We participated in the 8th Baltic Meeting on Microbial Carbohydrates this week. Ren and Roisin presented posters on their research at the meeting while Eoghan chaired the afternoon session on Tuesday. The meeting was held in Malahide, Dublin beyond the traditional geographical area of the conference (although the air-con was a little cold on one day it couldn’t be described as being ‘baltic’). The meeting was run by our colleagues from the Oscarson group – well done on a smoothly run conference folks!
Congratulations to our former undergraduate researchers Nathan, Joe, Cian, Jammah and Alan on their graduation today! This marks the culmination of 4 years of hard work on their BSc degrees in Chemistry, Medicinal Chemistry & Chemical Biology, and Chemistry with Environmental & Sustainable Chemistry, respectively. Well done all. Congratulations to Joe and Cian who finished joint top of the class in Medicinal Chemistry & Chemical Biology. Nathan and Joe are staying the UCD School of Chemistry for postgraduate research. We hope you enjoy the day and wish you all the best for the future.
We are looking for a postdoctoral fellow to join the group. An SFI-funded postdoctoral position is available in the group for 16-18 months. We are seeking a highly motivated chemist, skilled in Organic chemistry, to join the group. Applications can only be made through the UCD HR website (job reference number 010758). The closing date for applications is October 1st and there is some flexibility with respect to start date. See the job description on the UCD HR website for further details.
We welcome Joe Ruddy back to the lab. Following a really successful undergraduate research project in the lab on organocatalysis, Joe is starting an MSc in the group in the area of carbohydrate chemistry. Joe’s project is funded by SFI. We are all happy you are back.
Ren, Róisín and Eoghan all presented their research in the 29th International Carbohydrate Symposium in Lisbon this week. Ren and Róisín presented their work as posters, while Eoghan was an invited speaker. We all very much enjoyed the excellent meeting. We are especially grateful to Prof Amélia Pilar Rauter who was the Chair of the organising committee for all of her hard work.
Congratulations to Martin on publishing his first paper. The paper was published online in Synthesis and describes the large-scale synthesis of a chiral sulfide, isothiocineole, and its application in asymmetric epoxidations and aziridinations on multi-gram scale. The work is a collaboration with the Aggarwal group in the University of Bristol. Martin’s co-authors are Dr Johnathan Matlock, Dr Ona Illa (Universitat Autònoma de Barcelona), Eoghan and Prof Varinder Aggarwal.
Currently the paper can be read online (with a subscription) but an author’s copy will be posted on the group website soon, and a copy will be deposited in the UCD repository once an embargo period has passed.
Synthesis 2018, efirst. M P O’Fearraigh, J V Matlock, E M McGarrigle*, V K Aggarwal* — Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination. DOI: 10.1055/s-0037-1609580
The work in UCD was sponsored the University of Bristol, the Irish Research Council (GOIPG/2014/528), Science Foundation Ireland, and the Marie-Curie Action COFUND (11/SIRG/B2154).