CHEBI:43577 - 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid

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ChEBI Name 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid ChEBI ID CHEBI:43577 ChEBI ASCII Name 3-deoxy-alpha-D-manno-oct-2-ulopyranosonic acid Definition The α-anomer of 3-deoxy-D-manno-oct-2-ulopyranosonic acid. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ZINC000005851513 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C8H14O8 Net Charge 0 Average Mass 238.19196 Monoisotopic Mass 238.06887 InChI InChI=1S/C8H14O8/c9-2-4(11)6-5(12)3(10)1-8(15,16-6)7(13)14/h3-6,9-12,15H,1-2H2,(H,13,14)/t3-,4-,5-,6-,8-/m1/s1 InChIKey NNLZBVFSCVTSLA-HXUQBWEZSA-N SMILES [H][C@@]1(O[C@](O)(C[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)CO Roles Classification Chemical Role(s): Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) View more via ChEBI Ontology ChEBI Ontology Outgoing 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) is a 3-deoxy-D-manno-octulosonic acid (CHEBI:11791) 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) is conjugate acid of 3-deoxy-α-D-manno-oct-2-ulosonate (CHEBI:85986) Incoming α-D-Kdo-4P-O(CH2)3S(CH2)2NH(polyacrylamide) macromolecule (CHEBI:60587) has functional parent 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) α-D-Kdo-4P-OAll (CHEBI:60574) has functional parent 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) α-D-Kdo-5P-O(CH2)3S(CH2)2NH(polyacrylamide) macromolecule (CHEBI:60589) has functional parent 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) α-D-Kdo-5P-OAll (CHEBI:60573) has functional parent 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) 3-deoxy-α-D-manno-2-octulosonic acid 8-phosphate (CHEBI:42115) has functional parent 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid 4-phosphate (CHEBI:59491) has functional parent 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid 5-phosphate (CHEBI:59489) has functional parent 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) 5-deoxy-4-epi-2,3-dehydro-Kdo-(4→8)-α-Kdo (CHEBI:61570) has functional parent 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) 3-deoxy-α-D-manno-oct-2-ulosonate (CHEBI:85986) is conjugate base of 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) 3-deoxy-α-D-manno-oct-2-ulosonyl group (CHEBI:87956) is substituent group from 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (CHEBI:43577) IUPAC Name 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid Synonyms Sources 3-DEOXY-D-MANNO-OCT-2-ULOSONIC ACID PDBeChem α-2-keto-3-deoxyoctulosonic acid pyranose ChEBI α-Kdo ChEBI α-KDop ChEBI Kdo ChEBI Manual Xrefs Databases DB03548 DrugBank KDO PDBeChem View more database links Registry Numbers Types Sources 4234215 Reaxys Registry Number Reaxys 4843253 Beilstein Registry Number Beilstein Citations Wen L, Zheng Y, Li T, Wang PG (2016) Enzymatic synthesis of 3-deoxy-d-manno-octulosonic acid (KDO) and its application for LPS assembly. Bioorganic & medicinal chemistry letters 26, 2825-2828 [PubMed:27173798] [show Abstract] The studies of 3-deoxy-d-manno-octulosonic acid (KDO) have been hindered due to its limited availability. Herein, an efficient enzymatic system for the facile synthesis of KDO from easy-to-get starting materials is described. In this one-pot three-enzyme (OPME) system, d-ribulose 5-phosphate, which was prepared from d-xylose, was employed as starting materials. The reaction process involves the isomerization of d-ribulose 5-phosphate to d-arabinose 5-phosphate catalyzed by d-arabinose 5-phosphate isomerase (KdsD), the aldol condensation of d-arabinose 5-phosphate and phosphoenolpyruvate (PEP) catalyzed by KDO 8-phosphate synthetase (KdsA), and the hydrolysis of KDO-8-phosphate catalyzed by KDO 8-phosphate phosphatase (KdsC). By using this OPME system, 72% isolated yield was obtained. The obtained KDO was further transferred to lipid A by KDO transferase from Escherichia coli (WaaA). Erwin AL, Allen S, Ho DK, Bonthuis PJ, Jarisch J, Nelson KL, Tsao DL, Unrath WC, Watson ME, Gibson BW, Apicella MA, Smith AL (2006) Role of lgtC in resistance of nontypeable Haemophilus influenzae strain R2866 to human serum. Infection and immunity 74, 6226-6235 [PubMed:16966407] [show Abstract] We are investigating a nontypeable Haemophilus influenzae (NTHI) strain, R2866, isolated from a child with meningitis. R2866 is unusually resistant to killing by normal human serum. The serum 50% inhibitory concentration (IC50) for this strain is 18%, approaching that of encapsulated H. influenzae. R3392 is a derivative of R2866 that was found to have increased sensitivity to human serum (IC50, 1.5%). Analysis of tetrameric repeat regions within lipooligosaccharide (LOS) biosynthetic genes in both strains indicated that the glycosyltransferase gene lgtC was out of frame ("off") in most colonies of R3392 but in frame with its start codon ("on") in most colonies of the parent. We sought antigenic and biochemical evidence for modification of the LOS structure. In a whole-cell enzyme-linked immunosorbent assay, strain R3392 displayed reduced binding of the Galalpha1,4Gal-specific monoclonal antibody 4C4. Mass spectrometry analysis of LOS from strain R2866 indicated that the primary oligosaccharide glycoform contained four heptose and four hexose residues, while that of R3392 contained four heptose and three hexose residues. We conclude that the R2866 lgtC gene encodes a galactosyltransferase involved in synthesis of the 4C4 epitope, as in other strains, and that expression of lgtC is associated with the high-level serum resistance that has been observed for this strain. This is the first description of the genetic basis of high-level serum resistance in NTHI, as well as the first description of LOS composition in an NTHI strain for which the complete genome sequence has been determined. Last Modified 18 July 2016