CHEBI:91253 - GDP-valienol(2−)

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ChEBI Name GDP-valienol(2−) ChEBI ID CHEBI:91253 ChEBI ASCII Name GDP-valienol(2-) Definition An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of GDP-valienol; major species at pH 7.3. Stars This entity has been manually annotated by the ChEBI Team. Submitter Kristian Axelsen Supplier Information No supplier information found for this compound. Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C17H23N5O15P2 Net Charge -2 Average Mass 599.337 Monoisotopic Mass 599.06769 InChI InChI=1S/C17H25N5O15P2/c18-17-20-14-8(15(29)21-17)19-4-22(14)16-13(28)11(26)7(35-16)3-34-38(30,31)37-39(32,33)36-6-1-5(2-23)9(24)12(27)10(6)25/h1,4,6-7,9-13,16,23-28H,2-3H2,(H,30,31)(H,32,33)(H3,18,20,21,29)/p-2/t6-,7+,9+,10-,11+,12-,13+,16+/m0/s1 InChIKey SBXHHXUHVHYPDE-WPOGMVEHSA-L SMILES [C@@H]1([C@@H]([C@H]([C@H](C=C1CO)OP(OP(=O)(OC[C@@H]2[C@H]([C@H]([C@H](N3C=4N=C(NC(C4N=C3)=O)N)O2)O)O)[O-])([O-])=O)O)O)O ChEBI Ontology Outgoing GDP-valienol(2−) (CHEBI:91253) is a organophosphate oxoanion (CHEBI:58945) GDP-valienol(2−) (CHEBI:91253) is conjugate base of GDP-valienol (CHEBI:128754) Incoming GDP-valienol (CHEBI:128754) is conjugate acid of GDP-valienol(2−) (CHEBI:91253) IUPAC Name 5'-O-{[({[(1S,4R,5S,6R)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]oxy}phosphinato)oxy]phosphinato}guanosine Synonym Source GDP-valienol UniProt Manual Xref Database CPD-18787 MetaCyc View more database links Registry Number Type Source 21794281 Reaxys Registry Number Reaxys Citation Asamizu S, Yang J, Almabruk KH, Mahmud T (2011) Pseudoglycosyltransferase catalyzes nonglycosidic C-N coupling in validamycin a biosynthesis. Journal of the American Chemical Society 133, 12124-12135 (Source: SUBMITTER) [PubMed:21766819] [show Abstract] 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. Last Modified 18 April 2016