EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

N-acetyl-D-mannosamine

Supplier Sponsors

CAS Number: 3615-17-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:222-790-8
FDA UNII: X80PR7P73R
Nikkaji Web:J421.873F
MDL:MFCD00136044
XlogP3:-1.70 (est)
Molecular Weight:221.20975000
Formula:C8 H15 N O6
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
2-acetamido-2-deoxy-D-mannose >98.0%(LC)
Odor: characteristic
Use: A derivative of D-Mannosamine (M167000).
TCI AMERICA
For experimental / research use only.
N-Acetyl-D-mannosamine Monohydrate >98.0%(HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for N-acetyl-D-mannosamine usage levels up to:
 not for fragrance use.
 
Recommendation for N-acetyl-D-mannosamine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11096158
National Institute of Allergy and Infectious Diseases:Data
N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Chemidplus:0003615176
 
References:
 N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):11096158
Pubchem (cas):3615-17-6
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C00645
HMDB (The Human Metabolome Database):HMDB01129
FooDB:FDB028419
Export Tariff Code:2940.00.6000
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 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
 

Articles:

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.
 
Notes:
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