Catalytic asymmetric synthesis of Non-proteinogenic amino acids PhD

Department(s):
Chemistry
Entry requirements:
2:1+
Full-time:
3 years
Part-time:
not available
Reference number:
CM/MCK-2/2017
Start date:
01 July 2018
UK/EU fees:
TBC
International fees:
TBC
Location:
Loughborough
Application deadline:
01 April 2018

Achievements

5th

in the UK for Chemistry

Guardian University Guide 2018

New

£17m STEMLab facility

2017

Overview

Loughborough University is a top-ten rated university in England for research intensity (REF2014) and an outstanding 66% of the work of Loughborough’s academic staff who were eligible to be submitted to the REF was judged as ‘world-leading’ or ‘internationally excellent’, compared to a national average figure of 43%.

In choosing Loughborough for your research, you’ll work alongside academics who are leaders in their field. You will benefit from comprehensive support and guidance from our Doctoral College, including tailored careers advice, to help you succeed in your research and future career. 

Project detail

Chiral amino acids whether proteinogenic (derived from proteins) or non-proteinogenic are ubiquitous and integral building blocks of numerous natural products and drug candidate molecules (e.g. antibiotics vancomycin / amoxicillin). Currently the bench mark synthetic methodology for installing this chiral centre is the asymmetric Strecker reaction, which relies on using highly toxic HCN or TMSCN as its key reagent.

This research programme will address this issue by the formation of this key chiral centre contained within non-proteinogenic aryl- and hetero-aryl glycine amino acids via an asymmetric addition of arenes / heteroarenes to allenamides: a reaction commonly known as ‘hydroarylation’. Allenamides have become an increasingly valuable group of compounds that contain two double-bonds on an adjacent carbon which are then attached directly to a nitrogen atom tempered with an electron withdrawing functionality. We have previously shown that it is possible to selectively activate allenamides to nucleophilic attack using ‘gold-catalysis’. We will introduce this new chiral centre by an asymmetric ‘gold-catalysed’ hydroarylation reaction manifold. Once this ‘gold catalysed asymmetric hydroarylation’ transformation has been achieved the products of this transformation will then be converted, in only one synthetic step, to the desired aryl- and hetero-aryl glycine targets.

See: Kimber et al., Org. Lett. 2014, 16, 4606; Tet. Lett, 2015, 56, 350; Synlett 2012, 565; J. Org. Chem. 2010, 75, 5406; Org. Lett. 2010, 12, 1128.

Supervisors

Primary supervisor: Dr Marc Kimber

Find out more

For further project details email Dr Marc Kimber or register your interest and ask us a question.

Applicants should have, or expect to achieve, at least a 2:1 Honours degree (or equivalent) in Chemistry/Medicinal Chemistry.

A relevant Master's degree and / or experience in one or more of the following will be an advantage:
Chemistry / Medicinal Chemistry.

All students must also meet the minimum English Language requirements.

Fees and funding

UK/EU:
TBC
International:
TBC

Tuition fees cover the cost of your teaching, assessment and operating University facilities such as the library, IT equipment and other support services. University fees and charges can be paid in advance and there are several methods of payment, including online payments and payment by instalment. Special arrangements are made for payments by part-time students.

This is an open call for candidates who are sponsored or who have their own funding. If you do not have funding, you may still apply, however Institutional funding is not guaranteed. Outstanding candidates (UK/EU/International) without funding will be considered for funding opportunities which may become available in the School.

How to apply

All applications should be made online. Under programme name, select Chemistry. Please quote reference number: CM/MCK-2/2017

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