N-Carbamoyl-D-glucosamine
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00217 |
| CAS | 71868-25-2 |
| Molecular Weight | 222.20 |
| Molecular Formula | C7H14N2O6 |
Online Inquiry
Description
N-Carbamoyl-D-glucosamine N is an antibiotic produced by Streptomyces halstedii SF-1993. It has anti-gram-negative bacteria and fungi. Hexose, D-glucosamine and N-acetyl-D-glucosamine can antagonize its activity.
Specification
| Synonyms | D-Glucose, 2-((aminocarbonyl)amino)-2-deoxy- |
| IUPAC Name | [(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]urea |
| Canonical SMILES | C(C(C(C(C(C=O)NC(=O)N)O)O)O)O |
| InChI | InChI=1S/C7H14N2O6/c8-7(15)9-3(1-10)5(13)6(14)4(12)2-11/h1,3-6,11-14H,2H2,(H3,8,9,15)/t3-,4+,5+,6+/m0/s1 |
| InChI Key | VITVUDZBVHPRHH-SLPGGIOYSA-N |
Properties
| Appearance | Colorless needle Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria; fungi |
| Melting Point | 158-159°C |
Reference Reading
1. CV-1, a new antibiotic produced by a strain of Streptomyces sp. II. structure determination
T Yasuzawa, M Yoshida, M Ichimura, K Shirahata, H Sano J Antibiot (Tokyo). 1987 Jun;40(6):727-31. doi: 10.7164/antibiotics.40.727.
The structure of a new antibiotic, CV-1 was determined to be 1,2-diamino-1,2-N,N'-carbonyl-1,2-dideoxy-alpha-D-glucose hydrate by spectral and chemical studies. CV-1 possessed a unique open ring hemiaminal structure. CV-1 synthesized from N-carbamoyl-D-glucosamine was identical to material isolated from fermentation.
2. Isolation and identification of N-carbamoyl-beta-D-glucopyranosylamine from human serum
T Hamafuji, W Tsugawa, K Sode J Biochem Mol Biol Biophys. 2002 Oct;6(5):315-8. doi: 10.1080/1025814021000003247.
N-carbamoyl-beta-D-glucopyranosylamine (NCG) is a compound, which can chemically be synthesized by the condensation of glucose and urea by heating under acidic condition. In this study, we isolated and identified NCG and its anomer from human serum. This is the first study showing the occurrence and isolation of NCG from a natural source. The NCG level in human serum was estimated to be 71+/-33 microM using a glucose-3-dehydrogenase-based assay. Because NCG is not commercially used in foods or drugs, we conclude that the NCG isolated from human serum is synthesized from blood glucose and urea in vivo.
3. Relationship between serum N-carbamoyl-beta-D-glucopyranosylamine level and renal failure
Tetsuro Hamafuji, Wakako Tsugawa, Koji Sode Ren Fail. 2003 Jan;25(1):115-21. doi: 10.1081/jdi-120017474.
A statistical investigation was carried out on the distribution of serum N-carbamoyl-beta-D-glucopyranosylamine (NCG) among various patient groups. The serum NCG levels of patients treated in the departments of hemodialysis (131 +/- microM), nephritic syndrome (47 +/- 54 microM), and diabetes mellitus (55 +/- 70 microM) were significantly higher (p < 0.01) than those in other internal disease patients (18 +/- 22 microM) and healthy volunteers (6 +/- 22 microM). The serum NCG level was greatly reduced by hemodialysis therapy, however a return to initial NCG levels was observed within about one week. These results indicate that a high serum NCG level is a feature of renal failure patients, and a relationship was demonstrated between hyperuremia and NCG formation and accumulation in blood.
Recommended Products
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
