The University of Southampton
University of Southampton Institutional Repository

Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates the corresponding dimethyl and ester lactones: towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein

Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates the corresponding dimethyl and ester lactones: towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein
Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates the corresponding dimethyl and ester lactones: towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein
Trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates, 10b and 10c respectively, and dimethyl (2S,3R)- and (2R,3R)[2 [2-H-2(1)]-homocitric lactones, 11b and 11c respectively, have been synthesised from shikimic acid and [2-H-2]-shikimic acid by a route which defines the stereochemistry of the two chiral centres in each compound. The NMR spectra of these products will enable the stereochemistry of the biological reaction catalysed by homocitrate synthase and by the protein from the nifV gene to be elucidated.
enzymes synthesis stereospecific homocitrate shikimate enantiospecific synthesis lysine biosynthesis citrate synthase d-mannose acid hydroperoxide intermediate epoxidations alcohols
0040-4039
2093-2096
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Duffy, James E.S.
158057e8-e088-4313-9159-b2ebfb57a97e
Young, Douglas W.
e205a9a7-1851-4b08-9f71-1109df35a8e2
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Duffy, James E.S.
158057e8-e088-4313-9159-b2ebfb57a97e
Young, Douglas W.
e205a9a7-1851-4b08-9f71-1109df35a8e2

Tavassoli, Ali, Duffy, James E.S. and Young, Douglas W. (2005) Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates the corresponding dimethyl and ester lactones: towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein. Tetrahedron Letters, 46 (12), 2093-2096. (doi:10.1016/j.tetlet.2005.01.134).

Record type: Article

Abstract

Trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates, 10b and 10c respectively, and dimethyl (2S,3R)- and (2R,3R)[2 [2-H-2(1)]-homocitric lactones, 11b and 11c respectively, have been synthesised from shikimic acid and [2-H-2]-shikimic acid by a route which defines the stereochemistry of the two chiral centres in each compound. The NMR spectra of these products will enable the stereochemistry of the biological reaction catalysed by homocitrate synthase and by the protein from the nifV gene to be elucidated.

Full text not available from this repository.

More information

Published date: 2005
Keywords: enzymes synthesis stereospecific homocitrate shikimate enantiospecific synthesis lysine biosynthesis citrate synthase d-mannose acid hydroperoxide intermediate epoxidations alcohols

Identifiers

Local EPrints ID: 45304
URI: http://eprints.soton.ac.uk/id/eprint/45304
ISSN: 0040-4039
PURE UUID: b48a15cf-49af-442b-bd37-9ab3cc1e5cb9
ORCID for Ali Tavassoli: ORCID iD orcid.org/0000-0002-7420-5063

Catalogue record

Date deposited: 20 Mar 2007
Last modified: 07 Oct 2020 08:21

Export record

Altmetrics

Contributors

Author: Ali Tavassoli ORCID iD
Author: James E.S. Duffy
Author: Douglas W. Young

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×