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- Name help_outline 5''-phosphoribostamycin Identifier CHEBI:65082 Charge 2 Formula C17H37N4O13P InChIKeyhelp_outline YSYVVCNYHFEBSE-VVPCINPTSA-P SMILEShelp_outline [NH3+]C[C@H]1O[C@H](O[C@@H]2[C@@H]([NH3+])C[C@@H]([NH3+])[C@H](O)[C@H]2O[C@@H]2O[C@H](COP([O-])([O-])=O)[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 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 6,264 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ribostamycin Identifier CHEBI:65028 Charge 4 Formula C17H38N4O10 InChIKeyhelp_outline NSKGQURZWSPSBC-VVPCINPTSA-R SMILEShelp_outline [H][C@]1(O[C@H](CO)[C@@H](O)[C@H]1O)O[C@@H]1[C@@H](O)[C@H]([NH3+])C[C@H]([NH3+])[C@H]1O[C@H]1O[C@H](C[NH3+])[C@@H](O)[C@H](O)[C@H]1[NH3+] 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 phosphate Identifier CHEBI:43474 Charge -2 Formula HO4P InChIKeyhelp_outline NBIIXXVUZAFLBC-UHFFFAOYSA-L SMILEShelp_outline OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,002 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:33971 | RHEA:33972 | RHEA:33973 | RHEA:33974 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Unique O-ribosylation in the biosynthesis of butirosin.
Kudo F., Fujii T., Kinoshita S., Eguchi T.
Using a comparative genetics approach, one or more of the BtrA, BtrL, BtrP, and BtrV proteins encoded in the butirosin biosynthetic gene cluster (btr) from Bacillus circulans SANK72073 were identified as being responsible for an O-ribosylation process leading to the formation of ribostamycin, a ke ... >> More
Using a comparative genetics approach, one or more of the BtrA, BtrL, BtrP, and BtrV proteins encoded in the butirosin biosynthetic gene cluster (btr) from Bacillus circulans SANK72073 were identified as being responsible for an O-ribosylation process leading to the formation of ribostamycin, a key intermediate in this, and related antibiotic biosynthetic pathways. Functional analysis of the recombinantly expressed proteins revealed that both BtrL and BtrP were responsible for the ribosylation of neamine, using 5-phosphoribosyl-1-diphosphate (PRPP) as the ribosyl donor. Further detailed analysis indicated that this process occurs via two discrete steps: with BtrL first catalyzing the phosphoribosylaion of neamine to form 5''-phosphoribostamycin, followed by a BtrP-catalyzed dephosphorylation to generate ribostamycin. To the best of our knowledge, this is the first time that the functional characterization of a glycosyltransferase from an aminoglycoside biosynthetic gene cluster has been reported. << Less
Bioorg. Med. Chem. 15:4360-4368(2007) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.