N-acetyl-D-mannosamine

CAS: 3615-17-6 C8 H15 N O6 MW: 221.20975000

Identification

NameN-acetyl-D-mannosamine
CAS Number3615-17-6
EINECS222-790-8
FDA UNIIX80PR7P73R
Molecular FormulaC8 H15 N O6
Molecular Weight221.20975000
MDL NumberMFCD00136044
Nikkaji NumberJ421.873F
XlogP3-1.70 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Soluble in water, 1e+006 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryinformation only not used for fragrances or flavors
Recommendation for N-acetyl-D-mannosamine usage levels up tonot for fragrance use.
Recommendation for N-acetyl-D-mannosamine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

2- acetamido-2-deoxy-D-mannose D- mannose, 2-(acetylamino)-2-deoxy- N-[(2R,3S,4R,5S,6R)-2,4,5- trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide PubMed: Hyposialylated IgG activates endothelial IgG receptor FcγRIIB to promote obesity-induced insulin resistance. PubMed: Immobilization of sugars in supermacroporous cryogels for the purification of lectins by affinity chromatography. PubMed: Reactivation of hyperglycemia-induced hypocretin (HCRT) gene silencing by N-acetyl-d-mannosamine in the orexin neurons derived from human iPS cells. PubMed: Safety, pharmacokinetics and sialic acid production after oral administration of N-acetylmannosamine (ManNAc) to subjects with GNE myopathy. PubMed: Production and characterization of active recombinant human factor II with consistent sialylation. PubMed: Clinical trials in minimal change disease. PubMed: Nutritional stimulation of commensal oral bacteria suppresses pathogens: the prebiotic concept. PubMed: Vibrational Signatures of Isomeric Lithiated N-acetyl-D-hexosamines by Gas-Phase Infrared Multiple-Photon Dissociation (IRMPD) Spectroscopy. PubMed: Identification of key genes involved in polysaccharide bioflocculant synthesis in Bacillus licheniformis. PubMed: Internalization of a novel, huge lectin from Ibacus novemdentatus (slipper lobster) induces apoptosis of mammalian cancer cells. PubMed: A sialic acid aldolase from Peptoclostridium difficile NAP08 with 4-hydroxy-2-oxo-pentanoate aldolase activity. PubMed: NANS-mediated synthesis of sialic acid is required for brain and skeletal development. PubMed: Protein engineering of a bacterial N-acyl-d-glucosamine 2-epimerase for improved stability under process conditions. PubMed: Identification of genes associated with the penetration activity of the human type of Edwardsiella tarda EdwGII through human colon epithelial cell monolayers. PubMed: Chronic administration of N-acetyl-D-mannosamine improves age-associated impairment of long-term potentiation in the senescence-accelerated mouse. PubMed: Characterization of a novel N-acetylneuraminic acid lyase favoring N-acetylneuraminic acid synthesis. PubMed: Crystal structure of product-bound complex of UDP-N-acetyl-d-mannosamine dehydrogenase from Pyrococcus horikoshii OT3. PubMed: Crystal structures and functional studies clarify substrate selectivity and catalytic residues for the unique orphan enzyme N-acetyl-D-mannosamine dehydrogenase. PubMed: First functional and mutational analysis of group 3 N-acetylneuraminate lyases from Lactobacillus antri and Lactobacillus sakei 23K. PubMed: Cloning and characterization of two different L-type lectin genes from the Chinese mitten crab Eriocheir sinensis. PubMed: Angiopoietin-like 4 based therapeutics for proteinuria and kidney disease. PubMed: Reaction mechanism of N-acetylneuraminic acid lyase revealed by a combination of crystallography, QM/MM simulation, and mutagenesis. PubMed: N-acetyl-D-mannosamine treatment alleviates age-related decline in place-learning ability in dogs. PubMed: The structure and immunomodulatory activity on intestinal epithelial cells of the EPSs isolated from Lactobacillus helveticus sp. Rosyjski and Lactobacillus acidophilus sp. 5e2. PubMed: Structural basis for substrate specificity and mechanism of N-acetyl-D-neuraminic acid lyase from Pasteurella multocida. PubMed: New N-acyl-D-glucosamine 2-epimerases from cyanobacteria with high activity in the absence of ATP and low inhibition by pyruvate. PubMed: Cloning, expression, purification, crystallization and preliminary X-ray diffraction studies of N-acetylneuraminate lyase from methicillin-resistant Staphylococcus aureus. PubMed: Transforming growth factor beta receptor 2 (TGFBR2) changes sialylation in the microsatellite unstable (MSI) Colorectal cancer cell line HCT116. PubMed: Artificial and natural sialic acid precursors influence the angiogenic capacity of human umbilical vein endothelial cells. PubMed: Identification and characterization of cellobiose 2-epimerases from various aerobes. PubMed: Staining tumor cells with biotinylated ACL-I, a lectin isolated from the marine sponge, Axinella corrugata. PubMed: Characterization of a novel N-acetylneuraminate lyase from Staphylococcus carnosus TM300 and its application to N-acetylneuraminic acid production. PubMed: Functional assignment of gene AAC16202.1 from Rhodobacter capsulatus SB1003: new insights into the bacterial SDR sorbitol dehydrogenases family. PubMed: Metabolic monosaccharides altered cell responses to anticancer drugs. PubMed: A transposon site hybridization screen identifies galU and wecBC as important for survival of Yersinia pestis in murine macrophages. PubMed: Properties of BoAGE2, a second N-acetyl-D-glucosamine 2-epimerase from Bacteroides ovatus ATCC 8483. PubMed: New insights into human minimal change disease: lessons from animal models. PubMed: Designing a binding interface for control of cancer cell adhesion via 3D topography and metabolic oligosaccharide engineering. PubMed: Production of N-acetyl-D-neuraminic acid by use of an efficient spore surface display system. PubMed: New stabilized FastPrep-CLEAs for sialic acid synthesis. PubMed: Molecular characterization of a novel N-acetylneuraminate lyase from Lactobacillus plantarum WCFS1. PubMed: Podocyte-secreted angiopoietin-like-4 mediates proteinuria in glucocorticoid-sensitive nephrotic syndrome. PubMed: Comparison of phenotypic (Biolog System) and genotypic (random amplified polymorphic DNA-polymerase chain reaction, RAPD-PCR, and amplified fragment length polymorphism, AFLP) methods for typing Lactobacillus plantarum isolates from raw vegetables and fruits. PubMed: LmbE proteins from Bacillus cereus are de-N-acetylases with broad substrate specificity and are highly similar to proteins in Bacillus anthracis. PubMed: Creatine kinase is a bacteriostatic factor with a lectin-like activity. PubMed: Targeting pro-invasive oncogenes with short chain fatty acid-hexosamine analogues inhibits the mobility of metastatic MDA-MB-231 breast cancer cells. PubMed: UDP-GlcNAc2-epimerase regulates cell surface sialylation and ceramide-induced cell death in human malignant lymphoma. PubMed: Pasteurella multocida sialic acid aldolase: a promising biocatalyst. PubMed: A crosslinked inclusion body process for sialic acid synthesis. PubMed: Divergent evolution of function in the ROK sugar kinase superfamily: role of enzyme loops in substrate specificity. PubMed: Enhanced interferon-gamma secretion and antitumor activity of T-lymphocytes activated by dendritic cells loaded with glycoengineered myeloma antigens. PubMed: Modelling the reaction course of N-acetylneuraminic acid synthesis from N-acetyl-D-glucosamine--new strategies for the optimisation of neuraminic acid synthesis. PubMed: Purification, crystallization and preliminary X-ray diffraction studies of a putative UDP-N-acetyl-D-mannosamine dehydrogenase from Pyrococcus horikoshii OT3. PubMed: Metabolic expression of thiol-derivatized sialic acids on the cell surface and their quantitative estimation by flow cytometry. PubMed: Synthesis of non-natural ManNAc analogs for the expression of thiols on cell-surface sialic acids. PubMed: The central cavity from the (alpha/alpha)6 barrel structure of Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase contains two key histidine residues for reversible conversion. PubMed: Engineering of a sialic acid synthesis pathway in transgenic plants by expression of bacterial Neu5Ac-synthesizing enzymes. PubMed: Targeting glycosylation pathways and the cell cycle: sugar-dependent activity of butyrate-carbohydrate cancer prodrugs. PubMed: Engineering the sialic acid in organs of mice using N-propanoylmannosamine. PubMed: Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor. PubMed: Glycosylation is altered by ethanol in rat hippocampal cultured neurons. PubMed: Metabolic installation of thiols into sialic acid modulates adhesion and stem cell biology. PubMed: Accessibility of N-acyl-D-mannosamines to N-acetyl-D-neuraminic acid aldolase. PubMed: Increased expression of the selectin ligand sialyl-Lewis(x) by biochemical engineering of sialic acids. PubMed: Biochemical engineering of the acyl side chain of sialic acids stimulates integrin-dependent adhesion of HL60 cells to fibronectin. PubMed: Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives. PubMed: Transport of N-acetyl-D-mannosamine and N-acetyl-D-glucosamine in Escherichia coli K1: effect on capsular polysialic acid production. PubMed: O-specific polysaccharide of the marine bacterium "Alteromonas marinoglutinosa" NCIMB 1770. PubMed: Biochemical engineering of the N-acyl side chain of sialic acid: biological implications. PubMed: Structure of the O16 antigen of Stenotrophomonas maltophilia. PubMed: Isolation and characterisation of a serum lectin from blue gourami, Trichogaster trichopterus (Pallus). PubMed: Synthesis of glycophostones: cyclic phosphonate analogues of biologically relevant sugars PubMed: Multiple N-acetyl neuraminic acid synthetase (neuB) genes in Campylobacter jejuni: identification and characterization of the gene involved in sialylation of lipo-oligosaccharide. PubMed: PCR identification of the group A Neisseria meningitidis gene in cerebrospinal fluid. PubMed: Alkaline biocatalysis for the direct synthesis of N-acetyl-D-neuraminic acid (Neu5Ac) from N-acetyl-D-glucosamine (GlcNAc). PubMed: Biosynthesis of KDN (2-keto-3-deoxy-D-glycero-D-galacto-nononic acid). Identification and characterization of a KDN-9-phosphate synthetase activity from trout testis. PubMed: Determination of different amino sugar 2'-epimerase activities by coupling to N-acetylneuraminate synthesis. PubMed: Uptake of N-acetyl-D-mannosamine: an essential intermediate in polysialic acid biosynthesis by Escherichia coli K92. PubMed: Human renin-binding protein is the enzyme N-acetyl-D-glucosamine 2-epimerase. PubMed: Regulation of capsular polysialic acid biosynthesis by N-acetyl-D-mannosamine, an intermediate of sialic acid metabolism. PubMed: Characterization of the gene cassette required for biosynthesis of the (alpha1-->6)-linked N-acetyl-D-mannosamine-1-phosphate capsule of serogroup A Neisseria meningitidis. PubMed: Purification and characterization of N-acetylneuraminate synthase from Escherichia coli K1-M12. PubMed: Structure of the O18 antigen from Acinetobacter baumannii. PubMed: An efficient process for production of N-acetylneuraminic acid using N-acetylneuraminic acid aldolase. PubMed: N-acetyl-D-neuraminic acid lyase generates the sialic acid for colominic acid biosynthesis in Escherichia coli K1. PubMed: Collectin in a non-mammalian species: isolation and characterization of mannan-binding protein (MBP) from chicken serum. PubMed: N-acetyl-D-neuraminic acid synthesis in Escherichia coli K1 occurs through condensation of N-acetyl-D-mannosamine and pyruvate. PubMed: Tritium labelling of amino sugars at C-2 by alkaline epimerization in tritiated water. PubMed: Chitosan-mediated stimulation of macrophage function. PubMed: The structure of the O-antigenic chain of the lipopolysaccharide of Rhizobium trifolii 4s. PubMed: The three-dimensional structure of N-acetylneuraminate lyase from Escherichia coli. PubMed: Identification of a genetic locus involved in the biosynthesis of N-acetyl-D-mannosamine, a precursor of the (alpha 2-->8)-linked polysialic acid capsule of serogroup B Neisseria meningitidis. PubMed: Purification and characterization of mannan-binding protein from mouse serum. PubMed: Purification and characterization of a mannose-specific lectin from Shallot (Allium ascalonicum) bulbs. PubMed: Detection, isolation and characterization of multiple lectins from the haemolymph of the cockroach Blaberus discoidalis. PubMed: Functional and structural identification of a new lectin activity of Borrelia recurrentis spirochetes. PubMed: Cholinergic and dopaminergic agents which inhibit a passive avoidance response attenuate the paradigm-specific increases in NCAM sialylation state. PubMed: Structures of the O1B and O1C lipopolysaccharide antigens of Escherichia coli. PubMed: Biosynthesis of a nonphysiological sialic acid in different rat organs, using N-propanoyl-D-hexosamines as precursors. PubMed: Neuronal ganglioside increases dependent on the neuron--glia interaction in primary culture. PubMed: Lack of cell density-dependent changes in gangliosides of rat primary culture neurons. PubMed: Conglutinin exhibits a complement-dependent enhancement of the respiratory burst of phagocytes stimulated by E. coli. PubMed: Suppression of human natural killer cell activity by amino sugars. PubMed: Purification and properties of N-acyl-D-mannosamine dehydrogenase from Flavobacterium sp. 141-8. PubMed: The anticonvulsant sodium valproate specifically induces the expression of a rat glial heat shock protein which is identified as the collagen type IV receptor. PubMed: Remodeling of a rat hepatocyte plasma membrane glycoprotein. De- and reglycosylation of dipeptidyl peptidase IV. PubMed: Binding properties of a mannose-specific lectin from the snowdrop (Galanthus nivalis) bulb. PubMed: Gangliosides, or sialic acid, antagonize ethanol intoxication. PubMed: Inhibition of yeast binding to mouse peritoneal macrophages by wheat germ agglutinin: a novel effect of the lectin on phagocytic cells. PubMed: Demonstration in human plasma of a lectin activity analogous to that of bovine conglutinin. PubMed: The molecular basis of the hyaluronic acid-mediated stimulation of granulocyte function. PubMed: Alteration of cerebral ganglioside metabolism in developing Snell dwarf mice. PubMed: A neuraminidase from Trypanosoma cruzi removes sialic acid from the surface of mammalian myocardial and endothelial cells. PubMed: CMP-sialic acid, the sole sialosyl donor, is intra-axonally transported. PubMed: Accumulation of N-acetylneuraminic acid (sialic acid) in human fibroblasts cultured in the presence of N-acetylmannosamine. PubMed: alpha-D-mannosidase forms in chicken liver. PubMed: N-acetyl-D-mannosamine analogues as potential inhibitors of sialic acid biosynthesis. PubMed: UDP-N-acetyl-D-mannosamine dehydrogenase from Escherichia coli. PubMed: The metabolism of sialic acid in cystic fibrosis. PubMed: Lectins of distinct specificity in Rhodnius prolixus interact selectively with Trypanosoma cruzi. PubMed: Kinetic characterization of N-acetyl-D-glucosamine kinase from rat liver and kidney. PubMed: The isolation and preliminary characterization of N-acetyl-D-glucosamine kinase from rat kidney and liver. PubMed: Enzymatic formation of uridine diphosphate N-acetyl-D-mannosamine. PubMed: Ia antigenic specificities are oligosaccharide in nature: hapten-inhibition studies. PubMed: Stimulation of HeLa-S3 cell aggregation by sugars related to cell membrane in rotation culture. PubMed: Distribution of neuraminidase and n-acetylneuraminate lyase activities among corynebacteria, mycobacteria, and nocardias. PubMed: Coupled-enzyme system for measuring viral neuraminidase activity. PubMed: Studies on N-acetylneuraminic acid aldolase. PubMed: [Purification and some properties of N-acetyl-D-mannosamine kinase from liver of normal rats and rats with thyrotoxicosis]. PubMed: [Activity of N-acetyl-D-mannosamine kinase of rat liver under some pathological conditions]. PubMed: Administration of N-acetyl-D-mannosamine to mammals. PubMed: STUDIES ON NITROGEN-CONTAINING SUGARS. I. SYNTHESIS OF N-ACETYL-D-MANNOSAMINE FROM 1-NITRO-1-DEOXY-D-MANNITOL PENTAACETATE. PubMed: Enzymatic phosphorylation of N-acetyl-D-mannosamine. PubMed: Preparation of N-acetyl-neuraminic acid from N-acetyl-D-mannosamine. PubMed: Enzymic synthesis of N-acetyl-D-mannosamine.