1.02011-09-21 00:19:54 UTC2018-05-29 01:52:53 UTCFDB022807FructosamineFructosamine is a compound which can be considered as the result of a reaction between fructose and ammonia or an amine (with a molecule of water being released). A fructosamine is also formed when carbonyl group of glucose reacts with an amino group of a protein, as the double bond to oxygen moves from the end carbon atom to the next carbon atom and water is released. Fructosamines formed from blood proteins such as serum albumin are known as Glycated Serum Protein (GSP) or Glycated Albumin, and are used to identify the plasma glucose concentration over time and so assess diabetic control. (wikipedia)
Glucose molecules are joined to protein molecules to form stable ketoamines, or fructosamines, through glycation, a nonenzymatic mechanism involving a labile Schiff base intermediate and the Amadori rearrangement. The amount of fructosamine in serum is increased in diabetes mellitus owing to the abnormally high concentration of sugar in blood. The concentration of fructosamine in serum thus reflects the degree of glycemic control attained by the diabetic patient and is useful in monitoring the effectiveness of therapy in diabetes over a period of several weeks, in a manner analogous to the determination of glycated hemoglobin. Of the analytical approaches used to measure fructosamine, affinity chromatography with m-aminophenylboronic acid and the nitroblue tetrazolium reduction method appear to be the most practical means for clinical chemists to assay fructosamine quickly, economically, and accurately. Fructosamine values can readily distinguish normal individuals and diabetic patients in good glycemic control from diabetics in poor control. Unlike glycated hemoglobin, which reflects the average blood sugar concentration over the past six to eight weeks, fructosamine reflects the average blood sugar concentration over the past two to three weeks. Thus a clinical advantage is that fructosamine responds more quickly to changes in therapy, thereby allowing for improved glycemic control. It is used in conjunction with determinations of blood sugar and (or) of glycated hemoglobin, or by itself, the fructosamine assay can provide clinically useful information for the detection and control of diabetes. (PMID: 3319287) [HMDB]1-Amino-1-deoxy-D-fructoseD-IsoglucosamineC6H13NO5179.1711179.079372531(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol4429-04-3NC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1OInChI=1S/C6H13NO5/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,8-11H,1-2,7H2/t3-,4-,5+,6-/m1/s1IXZISFNWUWKBOM-ARQDHWQXSA-N belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.MonosaccharidesOrganic compoundsOrganic oxygen compoundsOrganooxygen compoundsCarbohydrates and carbohydrate conjugatesAliphatic heteromonocyclic compoundsHemiacetalsHydrocarbon derivativesMonoalkylaminesOrganopnictogen compoundsOxacyclic compoundsOxanesPolyolsSecondary alcoholsAlcoholAliphatic heteromonocyclic compoundAmineHemiacetalHydrocarbon derivativeMonosaccharideOrganic nitrogen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganopnictogen compoundOxacycleOxanePolyolPrimary aliphatic aminePrimary amineSecondary alcoholSolidlogp-2.71logs0.74solubility9.90e+02 g/llogp-2.9pka_strongest_acidic10.71pka_strongest_basic8.17iupac(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrolaverage_mass179.1711mono_mass179.079372531smilesNC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1OformulaC6H13NO5inchiInChI=1S/C6H13NO5/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,8-11H,1-2,7H2/t3-,4-,5+,6-/m1/s1inchikeyIXZISFNWUWKBOM-ARQDHWQXSA-Npolar_surface_area116.17refractivity38.02polarizability16.43rotatable_bond_count1acceptor_count6donor_count5physiological_charge1formal_charge0Specdb::NmrOneD10042Specdb::NmrOneD10043Specdb::NmrOneD10044Specdb::NmrOneD10045Specdb::NmrOneD10046Specdb::NmrOneD10047Specdb::NmrOneD10048Specdb::NmrOneD10049Specdb::NmrOneD10050Specdb::NmrOneD10051Specdb::NmrOneD10052Specdb::NmrOneD10053Specdb::NmrOneD10054Specdb::NmrOneD10055Specdb::NmrOneD10056Specdb::NmrOneD10057Specdb::NmrOneD10058Specdb::NmrOneD10059Specdb::NmrOneD10060Specdb::NmrOneD10061Specdb::CMs19459Specdb::CMs38233Specdb::CMs146832Specdb::MsIr1544Specdb::MsIr1545Specdb::MsIr1546Specdb::MsMs309259Specdb::MsMs309260Specdb::MsMs309261Specdb::MsMs353644Specdb::MsMs353645Specdb::MsMs353646Specdb::MsMs2358534Specdb::MsMs2358535Specdb::MsMs2358536Specdb::MsMs2603156Specdb::MsMs2603157Specdb::MsMs2603158HMDB0203024103#<Reference:0x00005556763690f8>#<Reference:0x0000555676368ec8>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Fructosamine-3-kinaseQ9H479FN3KG/T mismatch-specific thymine DNA glycosylaseQ13569TDGKetosamine-3-kinaseQ9HA64FN3KRP