Towards the stereoselective syntheses of 2-methylcitrate and 2-methylisocitrate and their use in studying the methylcitric acid cycle in Bacillus subtilis

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Jennifer Suzanne Harty Doyle (Creator)
The University of North Carolina at Greensboro (UNCG )
Web Site:
Jason Reddick

Abstract: Bacillus subtilis is a model organism and the entire genome has been sequenced. However, there is an incomplete understanding of the metabolic pathways that are encoded within the genome. A long-term goal of the Reddick research group is to gain a more complete understanding of the mmg operon. The overall objective is to complete the syntheses of 2-methylisocitrate and develop a stereoselective synthesis of 2-methylcitrate. The central hypotheses of these projects are that MmgF cleaves one of the enantiomers of 2-methylisocitrate to produce succinate and pyruvate, and MmgD 2-methylcitrate synthase produces heterochiral ((2S-3R) or (2R,3S))-2-methylcitrate. The completed syntheses will facilitate new investigations furthering the understanding of the mother cell metabolic (mmg) operon. The synthesis of (2RS, 3RS)-2-methylisocitrate has been completed with modified literature methods, and the synthesis of (2RS, 3SR)-2-methylisocitrate has required multiple modifications in order to make the synthesis reproducible. Previous graduate students either were unable to finish the synthesis or experienced reproducibility problems with this synthesis. The stereoselective synthesis of 2-methylcitrate has been designed and the initial steps in the synthesis have begun. The progress made in these two projects will allow the Reddick research group to reach its long-term goal of obtaining more information and a better understanding of Bacillus subtilis and the mmg operon.

Additional Information

Language: English
Date: 2018
2-methylcitrate, 2-methylisocitrate, Bacillus subtillis, Bioorganic, Methylcitrate cycle, Organic chemistry
Bioorganic chemistry
Bacillus subtilis
Krebs cycle

Email this document to