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- Name help_outline γ-L-glutamyl-butirosin B Identifier CHEBI:65086 Charge 3 Formula C26H51N6O15 InChIKeyhelp_outline YGLNWHGPOZHVMV-BHZFYAMWSA-Q SMILEShelp_outline [NH3+]C[C@H]1O[C@H](O[C@@H]2[C@@H]([NH3+])C[C@@H](NC(=O)[C@@H](O)CCNC(=O)CC[C@H]([NH3+])C([O-])=O)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H]([NH3+])[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline butirosin B Identifier CHEBI:65085 Charge 4 Formula C21H45N5O12 InChIKeyhelp_outline XEQLFNPSYWZPOW-HBYCGHPUSA-R SMILEShelp_outline [NH3+]CC[C@H](O)C(=O)N[C@@H]1C[C@H]([NH3+])[C@@H](O[C@H]2O[C@H](C[NH3+])[C@@H](O)[C@H](O)[C@H]2[NH3+])[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H]1O 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 5-oxo-L-proline Identifier CHEBI:58402 (Beilstein: 4783230) help_outline Charge -1 Formula C5H6NO3 InChIKeyhelp_outline ODHCTXKNWHHXJC-VKHMYHEASA-M SMILEShelp_outline [O-]C(=O)[C@@H]1CCC(=O)N1 2D coordinates Mol file for the small molecule Search links Involved in 6 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:33995 | RHEA:33996 | RHEA:33997 | RHEA:33998 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain.
Llewellyn N.M., Li Y., Spencer J.B.
Butirosin, an aminoglycoside antibiotic produced by Bacillus circulans, bears the unique (S)-4-amino-2-hydroxybutyrate (AHBA) side chain, which protects the antibiotic from several common resistance mechanisms. The AHBA side chain is advantageously incorporated into clinically valuable antibiotics ... >> More
Butirosin, an aminoglycoside antibiotic produced by Bacillus circulans, bears the unique (S)-4-amino-2-hydroxybutyrate (AHBA) side chain, which protects the antibiotic from several common resistance mechanisms. The AHBA side chain is advantageously incorporated into clinically valuable antibiotics such as amikacin and arbekacin by synthetic methods. Therefore, it is of significant interest to explore the biosynthetic origins of this useful moiety. We report here that the AHBA side chain of butirosin is transferred from the acyl carrier protein (ACP) BtrI to the parent aminoglycoside ribostamycin as a gamma-glutamylated dipeptide by the ACP:aminoglycoside acyltransferase BtrH. The protective gamma-glutamyl group is then cleaved by BtrG via an uncommon gamma-glutamyl cyclotransferase mechanism. The application of this pathway to the in vitro enzymatic production of novel AHBA-bearing aminoglycosides is explored with encouraging implications for the preparation of unnatural antibiotics via directed biosynthesis. << Less
Chem. Biol. 14:379-386(2007) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.