UCL Discovery
UCL home » Library Services » Electronic resources » UCL Discovery

Synthesis and photolytic evaluation of a nitroindoline-caged glycine with a side chain of high negative charge for use in neuroscience

Papageorgiou, G; Beato, M; Ogden, D; (2011) Synthesis and photolytic evaluation of a nitroindoline-caged glycine with a side chain of high negative charge for use in neuroscience. Tetrahedron , 67 (29) 5228 - 5234. 10.1016/j.tet.2011.05.045. Green open access

[thumbnail of Beato_Papageorgiou et al 2011.pdf]
Preview
Text
Beato_Papageorgiou et al 2011.pdf

Download (660kB) | Preview

Abstract

A photolabile precursor of the neuroinhibitory amino acid glycine has been synthesised with two phosphate groups attached to the indoline nucleus at a 4-alkoxy substituent. In common with the photochemical properties of other 1-acyl-7-nitroindolines, this releases glycine on a sub-is time scale upon irradiation with near-UV light. The synthetic route previously developed for the preparation of the GABA analogue required some modifications because of the greater hydrolytic sensitivity of the glycine compound. The phosphorylation method used here could be beneficial to the synthesis of other nitroindoline-caged amino acids, especially the related caged GABA derivative. Glycine released by laser photolysis on spinal cord neurons generated fast-rising responses and the pharmacological properties of the reagent are such that it is useful for physiological experiments.

Type: Article
Title: Synthesis and photolytic evaluation of a nitroindoline-caged glycine with a side chain of high negative charge for use in neuroscience
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tet.2011.05.045
Publisher version: http://dx.doi.org/10.1016/j.tet.2011.05.045
Language: English
Additional information: © 2011. This manuscript version is published under a Creative Commons Attribution Non-commercial Non-derivative 4.0 International licence (CC BY-NC-ND 4.0). This licence allows you to share, copy, distribute and transmit the work for personal and non-commercial use providing author and publisher attribution is clearly stated. Further details about CC BY licences are available at http://creativecommons.org/licenses/by/4.0.
Keywords: Photolysis, Caged compounds, Nitroindolines, Phosphorylation, metabotropic slow EPSC, rat Purkinje neurons, dendritic spines, l-glutamate, carboxylic-acids, gaba receptors, 1-acyl-7-nitroindolines, photorelease, transporters, mechanisms
UCL classification: UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > Div of Biosciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > Div of Biosciences > Neuro, Physiology and Pharmacology
URI: https://discovery.ucl.ac.uk/id/eprint/1320074
Downloads since deposit
238Downloads
Download activity - last month
Download activity - last 12 months
Downloads by country - last 12 months

Archive Staff Only

View Item View Item