| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:32 -0600 |
| Update Date |
2013-02-08 17:11:13 -0700 |
| HMDB ID |
HMDB02030 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Fructosamine |
| Description |
Fructosamine 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. Fructosamine 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  ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-Amino-1-deoxy-D-fructose
- D-Isoglucosamine
|
| Chemical Formula |
C6H13NO5 |
| Average Molecular Weight |
179.1711 |
| Monoisotopic Molecular Weight |
179.079372531 |
| IUPAC Name |
(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol |
| Traditional IUPAC Name |
(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol |
| CAS Registry Number |
4429-04-3 |
| SMILES |
NC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O |
| InChI Identifier |
InChI=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/s1 |
| InChI Key |
IXZISFNWUWKBOM-ARQDHWQXSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Carbohydrates and Carbohydrate Conjugates |
| Class |
Monosaccharides |
| Sub Class |
Hexoses |
| Other Descriptors |
- Aliphatic Heteromonocyclic Compounds
- Carbohydrates and Carbohydrate Conjugates
|
| Substituents |
- 1,2 Diol
- Hemiacetal
- Oxane
- Primary Aliphatic Amine (Alkylamine)
- Secondary Alcohol
|
| Direct Parent |
Hexoses |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
Not Available |
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
Not Available
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| Biofluid Locations |
|
| Tissue Location |
Not Available
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| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
1980 +/- 320 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
2300 (1850 - 2850) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
192 (149–242) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
4750.0 +/- 2950.0 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
<1.00 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
2220 +/- 250 uM |
Adult (>18 years old) |
Female |
Pregnancy |
Not Available |
| Blood |
Detected and Quantified |
|
338.7 +/- 77.4 uM |
Adult (>18 years old) |
Both |
Diabetes |
Type 1 with oral insulin spray treatment
|
| Blood |
Detected and Quantified |
|
228 (180–255) uM |
Adult (>18 years old) |
Both |
Cirrhosis |
Not Available |
| Blood |
Detected and Quantified |
|
315 (260–430) uM |
Adult (>18 years old) |
Both |
Renal disease |
Not Available |
| Blood |
Detected and Quantified |
|
254 (193–315) uM |
Adult (>18 years old) |
Both |
Type 2 diabetes (Good control) |
Not Available |
| Blood |
Detected and Quantified |
|
408 (346–653) uM |
Adult (>18 years old) |
Both |
Type 2 diabetes (Poor control) |
Not Available |
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Diabetes mellitus type 2 |
|---|
- Guevara-Aguirre J, Guevara-Aguirre M, Saavedra J, Bernstein G, Rosenbloom AL: Comparison of oral insulin spray and subcutaneous regular insulin at mealtime in type 1 diabetes. Diabetes Technol Ther. 2007 Aug;9(4):372-6.
Pubmed: 17705693
|
| Pregnancy |
|---|
- Khan HA, Sobki SH, Alhomida AS: Fluctuations in fasting blood glucose and serum fructosamine in pregnant women monitored on successive antenatal visits. Clin Exp Med. 2006 Oct;6(3):134-7.
Pubmed: 17061063
|
| 11-beta-hydroxylase deficiency |
|---|
- Paroni R, Ceriotti F, Galanello R, Battista Leoni G, Panico A, Scurati E, Paleari R, Chemello L, Quaino V, Scaldaferri L, Lapolla A, Mosca A: Performance characteristics and clinical utility of an enzymatic method for the measurement of glycated albumin in plasma. Clin Biochem. 2007 Dec;40(18):1398-405. Epub 2007 Aug 10.
Pubmed: 17919531
|
|
| Associated OMIM IDs |
- 202010 (11-beta-hydroxylase deficiency)
- 125853 (Diabetes mellitus type 2)
|
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022807 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
19291 |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Fructosamine |
| NuGOwiki Link |
HMDB02030 |
| Metagene Link |
HMDB02030 |
| METLIN ID |
Not Available |
| PubChem Compound |
20484 |
| PDB ID |
Not Available |
| ChEBI ID |
24103 |
| References |
|---|
| Synthesis Reference |
Liu, Gui-Rong; Qiu, Ye; Yang, Qun-Shui. Synthesis of fructosamine and its application in cigarettes. Yancao Keji (2006), (8), 33-34, 37. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Morenkova SA: [Comparative analysis of dependence of saliva sorbitol and fructosamine levels on blood glucose level in patients with diabetes] Biomed Khim. 2004;50(6):612-4.
Pubmed: 15707277
|
