GoldI-catalysed Synthesis of a Furan Analogue of Thiamine PyrophosphateReportar como inadecuado


GoldI-catalysed Synthesis of a Furan Analogue of Thiamine Pyrophosphate


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Publication Date: 2014-11-05

Journal Title: Beilstein Journal of Organic Chemistry

Publisher: Beilstein-Institut

Volume: 10

Pages: 2580-2585

Language: English

Type: Article

Metadata: Show full item record

Citation: Iqbal, A., Sahraoui, E., & Leeper, F. J. (2014). Gold(I)-catalysed Synthesis of a Furan Analogue of Thiamine Pyrophosphate. Beilstein Journal of Organic Chemistry, 10 2580-2585.

Description: This is the final version. It was first published by the Beilstein-Institut at http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-10-270

Abstract: An analogue of thiamine having a furan ring in place of the thiazolium ring has been synthesised by a short and efficient route, involving gold(I)-catalysed cyclisation of an alkynyl alcohol to form the furan ring. The furan analogue of thiamine diphosphate (ThDP) was also made and tested for binding to and inhibition of pyruvate decarboxylase (PDC) from Zymomonas mobilis (overexpressed in E. coli with a N-terminal His-tag). It is a very strong inhibitor, with a KI value of 32.5 pM. It was also shown that the furan analogue of thiamine can be functionalised at the C-2 position, which will allow access to mimics of reaction intermediates of various ThDP-dependent enzymes.

Keywords: Thiamine diphosphate, Gold-catalysed cyclisation, Furan Synthesis, Pyruvate decarboxylase

Sponsorship: This work was supported by a studentship from the Cambridge Commonwealth Trust (A.I.)

Identifiers:

This record's URL: http://www.repository.cam.ac.uk/handle/1810/246187http://dx.doi.org/10.3762/bjoc.10.270

Rights: Attribution 2.0 UK: England & Wales

Licence URL: http://creativecommons.org/licenses/by/2.0/uk/





Autor: Iqbal, AmjidSahraoui, El-HabibLeeper, Finian J.

Fuente: https://www.repository.cam.ac.uk/handle/1810/246187



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