Abstract

Trifolitoxin (TFX) is a peptide bacteriocin produced by Rhizobium leguminosarum bv. trifoli T24 which is bacteriostatic toward most strains of R. leguminosarum and R. fredii. Sequence analysis of the TFX production and resistance genes strongly suggests that this peptide is produced ribosomally (Breil, et al. 1993, J. Bacteriol., in press). The DNA sequence of the tfxA structural gene and Edman degradation of the purified peptide show that the amino acid sequence of the peptide precursor of TFX is DIGGSRQGCVA. This peptide sequence is post-translationally modified by the tfx genes such that the glutamine residue is cyclized to a UV absorbing chromophore. The purpose of this work was to determine the structure of this chromophore. Two isomers of TFX were isolated by reverse phase HPLC. The mass of the molecules was confirmed by low resolution FAB-MS to be 1037.4 for both molecules. The structure of the chromophore was determined by a combination of modern NMR techniques, such as COSY, TOCSY and HMQC, to be a 2-pyridone derivative which tautomerizes to give TFX isomers. Both isomers of TFX also contain a thiazoline ring which is the result of ring closure between the sulfhydryl group of cysteine and the carbonyl of glycine.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Center for Research Resources (NCRR)
Type
Biotechnology Resource Grants (P41)
Project #
5P41RR002301-17
Application #
6451277
Study Section
Project Start
2001-03-01
Project End
2002-02-28
Budget Start
Budget End
Support Year
17
Fiscal Year
2001
Total Cost
Indirect Cost

  Institution

Name
University of Wisconsin Madison
Department
Type
DUNS #
161202122
City
Madison
State
WI
Country
United States
Zip Code
53715

  Publications

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Franco, Aldo; Dovell, Sanaz; Möller, Carolina et al. (2018) Structural plasticity of mini-M conotoxins - expression of all mini-M subtypes by Conus regius. FEBS J 285:887-902
Wales, Jessica A; Chen, Cheng-Yu; Breci, Linda et al. (2018) Discovery of stimulator binding to a conserved pocket in the heme domain of soluble guanylyl cyclase. J Biol Chem 293:1850-1864
Travers, Timothy; López, Cesar A; Van, Que N et al. (2018) Molecular recognition of RAS/RAF complex at the membrane: Role of RAF cysteine-rich domain. Sci Rep 8:8461
Thomas, Nathan E; Wu, Chao; Morrison, Emma A et al. (2018) The C terminus of the bacterial multidrug transporter EmrE couples drug binding to proton release. J Biol Chem 293:19137-19147
Assadi-Porter, Fariba M; Radek, James; Rao, Hongyu et al. (2018) Multimodal Ligand Binding Studies of Human and Mouse G-Coupled Taste Receptors to Correlate Their Species-Specific Sweetness Tasting Properties. Molecules 23:
Wijayatunga, Nadeeja N; Sams, Valerie G; Dawson, John A et al. (2018) Roux-en-Y gastric bypass surgery alters serum metabolites and fatty acids in patients with morbid obesity. Diabetes Metab Res Rev 34:e3045
Assadi-Porter, Fariba M; Reiland, Hannah; Sabatini, Martina et al. (2018) Metabolic Reprogramming by 3-Iodothyronamine (T1AM): A New Perspective to Reverse Obesity through Co-Regulation of Sirtuin 4 and 6 Expression. Int J Mol Sci 19:
Selen Alpergin, Ebru S; Bolandnazar, Zeinab; Sabatini, Martina et al. (2017) Metabolic profiling reveals reprogramming of lipid metabolic pathways in treatment of polycystic ovary syndrome with 3-iodothyronamine. Physiol Rep 5:
Mong, Surin K; Cochran, Frank V; Yu, Hongtao et al. (2017) Heterochiral Knottin Protein: Folding and Solution Structure. Biochemistry 56:5720-5725

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