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- Name help_outline D-allo-threonine Identifier CHEBI:58645 Charge 0 Formula C4H9NO3 InChIKeyhelp_outline AYFVYJQAPQTCCC-PWNYCUMCSA-N SMILEShelp_outline C[C@@H](O)[C@@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline D-leucine Identifier CHEBI:143079 Charge 0 Formula C6H13NO2 InChIKeyhelp_outline ROHFNLRQFUQHCH-RXMQYKEDSA-N SMILEShelp_outline [O-]C([C@@H](CC(C)C)[NH3+])=O 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline D-alanine Identifier CHEBI:57416 Charge 0 Formula C3H7NO2 InChIKeyhelp_outline QNAYBMKLOCPYGJ-UWTATZPHSA-N SMILEShelp_outline C[C@@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 30 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline L-proline Identifier CHEBI:60039 Charge 0 Formula C5H9NO2 InChIKeyhelp_outline ONIBWKKTOPOVIA-BYPYZUCNSA-N SMILEShelp_outline [O-]C(=O)[C@@H]1CCC[NH2+]1 2D coordinates Mol file for the small molecule Search links Involved in 30 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline L-leucine Identifier CHEBI:57427 Charge 0 Formula C6H13NO2 InChIKeyhelp_outline ROHFNLRQFUQHCH-YFKPBYRVSA-N SMILEShelp_outline CC(C)C[C@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 55 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 3,077 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline fusahexin Identifier CHEBI:191392 Charge 0 Formula C30H50N6O7 InChIKeyhelp_outline KALBWDFILFPIEW-MGESPVMDSA-N SMILEShelp_outline [C@H]1(C(N[C@H](C(N[C@H]2C(=O)N3[C@H](C(N[C@@H](C(N[C@H](C(=O)N1)CC(C)C)=O)CC(C)C)=O)CC[C@H]3O[C@@H]2C)=O)CC(C)C)=O)C 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 3,005 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:72047 | RHEA:72048 | RHEA:72049 | RHEA:72050 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Cyclic, hydrophobic hexapeptide fusahexin is the product of a nonribosomal peptide synthetase in Fusarium graminearum.
Westphal K.R., Bachleitner S., Severinsen M.M., Brundtoe M.L., Hansen F.T., Soerensen T., Wollenberg R.D., Lysoee E., Studt L., Soerensen J.L., Sondergaard T.E., Wimmer R.
The plant pathogenic fungus <i>Fusarium graminearum</i> is known to produce a wide array of secondary metabolites during plant infection. This includes several nonribosomal peptides. Recently, the fusaoctaxin (<i>NRPS5</i>/9) and gramilin (<i>NRPS8</i>) gene clusters were shown to be induced by ho ... >> More
The plant pathogenic fungus <i>Fusarium graminearum</i> is known to produce a wide array of secondary metabolites during plant infection. This includes several nonribosomal peptides. Recently, the fusaoctaxin (<i>NRPS5</i>/9) and gramilin (<i>NRPS8</i>) gene clusters were shown to be induced by host interactions. To widen our understanding of this important pathogen, we investigated the involvement of the <i>NRPS4</i> gene cluster during infection and oxidative and osmotic stress. Overexpression of <i>NRPS4</i> led to the discovery of a new cyclic hexapeptide, fusahexin (<b>1</b>), with the amino acid sequence cyclo-(d-Ala-l-Leu-d-<i>allo</i>-Thr-l-Pro-d-Leu-l-Leu). The structural analyses revealed an unusual ether bond between a proline C<sup>δ</sup> to C<sup>β</sup> of the preceding threonine resulting in an oxazine ring system. The comparative genomic analyses showed that the small gene cluster only encodes an ABC transporter in addition to the five-module nonribosomal peptide synthetase (NRPS). Based on the structure of fusahexin and the domain architecture of <i>NRPS4</i>, we propose a biosynthetic model in which the terminal module is used to incorporate two leucine units. So far, iterative use of NRPS modules has primarily been described for siderophore synthetases, which makes <i>NRPS4</i> a rare example of a fungal nonsiderophore NRPS with distinct iterative module usage. << Less