Post translational modifications of Trifolitoxin: a blue fluorescent peptide antibiotic

Affiliations

¹ School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA, 5064, Australia.
² School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA, 5064, Australia. robert.asenstorfer@adelaide.edu.au.
³ Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL, 32611-7200, USA.
⁴ PK Yonge Developmental Research School, University of Florida, Gainesville, FL, 32601-7845, USA.
⁵ Mass Spectrometry Research and Education Center, Chemistry Department, University of Florida, Florida, FL, 32611-7200, USA.
⁶ Departamento de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 23851-970, RJ, Brazil.
⁷ Department of Plant Pathology, University of California, Riverside, CA, 92521, USA.
⁸ Department of Agronomy, University of Wisconsin-Madison, Madison, WI, 53706, USA.
⁹ Department of Microbiology and Cell Science, University of Florida, Gainesville, FL, 32611-7200, USA.

PMID: 35022574
PMCID: PMC8816728
DOI: 10.1038/s41429-021-00497-0

Post translational modifications of Trifolitoxin: a blue fluorescent peptide antibiotic

Benjamin J Lethbridge et al. J Antibiot (Tokyo). 2022 Mar.

. 2022 Mar;75(3):125-135.

doi: 10.1038/s41429-021-00497-0. Epub 2022 Jan 12.

Authors

Affiliations

¹ School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA, 5064, Australia.
² School of Agriculture, Food and Wine, University of Adelaide, Waite Campus, Urrbrae, SA, 5064, Australia. robert.asenstorfer@adelaide.edu.au.
³ Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL, 32611-7200, USA.
⁴ PK Yonge Developmental Research School, University of Florida, Gainesville, FL, 32601-7845, USA.
⁵ Mass Spectrometry Research and Education Center, Chemistry Department, University of Florida, Florida, FL, 32611-7200, USA.
⁶ Departamento de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 23851-970, RJ, Brazil.
⁷ Department of Plant Pathology, University of California, Riverside, CA, 92521, USA.
⁸ Department of Agronomy, University of Wisconsin-Madison, Madison, WI, 53706, USA.
⁹ Department of Microbiology and Cell Science, University of Florida, Gainesville, FL, 32611-7200, USA.

PMID: 35022574
PMCID: PMC8816728
DOI: 10.1038/s41429-021-00497-0

Abstract

Trifolitoxin (TFX, C₄₁H₆₃N₁₅O₁₅S) is a selective, ribosomally-synthesized, post-translationally modified, peptide antibiotic, produced by Rhizobium leguminosarum bv. trifolii T24. TFX specifically inhibits α-proteobacteria, including the plant symbiont Rhizobium spp., the plant pathogen Agrobacterium spp. and the animal pathogen Brucella abortus. TFX-producing strains prevent legume root nodulation by TFX-sensitive rhizobia. TFX has been isolated as a pair of geometric isomers, TFX1 and TFX2, which are derived from the biologically inactive primary amino acid sequence: Asp-Ile-Gly-Gly-Ser-Arg-Gln-Gly-Cys-Val-Ala. Gly-Cys is present as a thiazoline ring and the Arg-Gln-Gly sequence is extensively modified to a UV absorbing, blue fluorescent chromophore. The chromophore consists of a conjugated, 5-membered heterocyclic ring and side chain of modified glutamine.

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Conflict of interest statement

The authors declare no competing interests.

Figures

**Fig. 1**
Unmodified TFX peptide with the results of the chemical analyses of the biologically active TFX peptide

**Fig. 2**
Structure of TFX in aqueous solution

See this image and copyright information in PMC

References

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1. Triplett EW, Breil BT, Splitter GA. Expression of tfx and sensitivity to the Rhizobial peptide antibiotic trifolitoxin in a taxonomically distinct group of α-proteobacteria including the animal pathogen Brucella abortus. Appl Environ Microbiol. 1994;60:4163–6. - PMC - PubMed
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Post translational modifications of Trifolitoxin: a blue fluorescent peptide antibiotic

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Post translational modifications of Trifolitoxin: a blue fluorescent peptide antibiotic

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