Reaction participants Show >> << Hide
- Name help_outline validoxylamine A 7'-phosphate Identifier CHEBI:111504 Charge -1 Formula C14H25NO11P InChIKeyhelp_outline ZKSTYMJGEHZSFH-MBABXGOBSA-M SMILEShelp_outline C1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1COP([O-])(=O)[O-])O)O)O)[NH2+][C@@H]2[C@@H]([C@H]([C@@H](C(=C2)CO)O)O)O 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 validoxylamine A Identifier CHEBI:111505 Charge 1 Formula C14H26NO8 InChIKeyhelp_outline YCJYNBLLJHFIIW-MBABXGOBSA-O SMILEShelp_outline C1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O)[NH2+][C@@H]2[C@@H]([C@H]([C@@H](C(=C2)CO)O)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 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:49400 | RHEA:49401 | RHEA:49402 | RHEA:49403 | |
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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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Pseudoglycosyltransferase catalyzes nonglycosidic C-N coupling in validamycin a biosynthesis.
Asamizu S., Yang J., Almabruk K.H., Mahmud T.
Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-pho ... >> More
Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented nonglycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated 'pseudoglycosyltransferase' catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7'-phosphate with net retention of the 'anomeric' configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7'-phosphate to validoxylamine A. << Less
J. Am. Chem. Soc. 133:12124-12135(2011) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.