3-Amino-3-deoxy-D-glucose
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| Category | Bioactive by-products |
| Catalog number | BBF-00677 |
| CAS | 576-44-3 |
| Molecular Weight | 179.17 |
| Molecular Formula | C6H13NO5 |
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Description
It is produced by the strain of Bacillus aminoglucosidicus. It has the activity of resistant bacillus subtilis and other gram-positive bacteria.
Specification
| Synonyms | D-Kanosamine; Kanosamine |
| Storage | -20 °C under inert atmosphere |
| IUPAC Name | (3R,4S,5S,6R)-4-amino-6-(hydroxymethyl)oxane-2,3,5-triol |
| Canonical SMILES | C(C1C(C(C(C(O1)O)O)N)O)O |
| InChI | InChI=1S/C6H13NO5/c7-3-4(9)2(1-8)12-6(11)5(3)10/h2-6,8-11H,1,7H2/t2-,3+,4-,5-,6?/m1/s1 |
| InChI Key | BQCCAEOLPYCBAE-CBPJZXOFSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 530.5±50.0 °C (Predicted) |
| Melting Point | 140-143 °C |
| Density | 1.491±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Water |
Reference Reading
1. 3-Amino-3-deoxy-D-glucose: an antibiotic produced by a deep-sea bacterium
N Fusetani, D Ejima, S Matsunaga, K Hashimoto, K Itagaki, Y Akagi, N Taga, K Suzuki Experientia. 1987 Apr 15;43(4):464-5. doi: 10.1007/BF01940457.
Gram-positive bacteria isolated from deep-sea sediments of the Pacific basin showed considerable antibacterial activity. A Bacillus strain, isolated from a sediment sample collected at a depth of 4310 m, was shown to produce 3-amino-3-deoxy-D-glucose, a known antibiotic.
2. Stepwise Post-glycosylation Modification of Sugar Moieties in Kanamycin Biosynthesis
Fumitaka Kudo, Yukinobu Kitayama, Akimasa Miyanaga, Mario Numakura, Tadashi Eguchi Chembiochem. 2021 May 4;22(9):1668-1675. doi: 10.1002/cbic.202000839. Epub 2021 Feb 11.
Kanamycin A is the major 2-deoxystreptamine (2DOS)-containing aminoglycoside antibiotic produced by Streptomyces kanamyceticus. The 2DOS moiety is linked with 6-amino-6-deoxy-d-glucose (6ADG) at O-4 and 3-amino-3-deoxy-d-glucose at O-6. Because the 6ADG moiety is derived from d-glucosamine (GlcN), deamination at C-2 and introduction of C-6-NH2 are required in the biosynthesis. A dehydrogenase, KanQ, and an aminotransferase, KanB, are presumed to be responsible for the introduction of C-6-NH2 , although the substrates have not been identified. Here, we examined the substrate specificity of KanQ to better understand the biosynthetic pathway. It was found that KanQ oxidized kanamycin C more efficiently than the 3''-deamino derivative. Furthermore, the substrate specificity of an oxygenase, KanJ, that is responsible for deamination at C-2 of the GlcN moiety was examined, and the crystal structure of KanJ was determined. It was found that C-6-NH2 is important for substrate recognition by KanJ. Thus, the modification of the GlcN moiety occurs after pseudo-trisaccharide formation, followed by the introduction of C-6-NH2 by KanQ/KanB and deamination at C-2 by KanJ.
3. The site of inhibition of cell wall synthesis by 3-amino-3-deoxy-D-glucose in Staphylococcus aureus
H Tanaka, S Shimizu, R Oiwa, Y Iwai, S Omura J Biochem. 1979 Jul;86(1):155-9.
The inhibition of growth and cell wall synthesis by 3-amino-3-deoxy-D-glucose (3-AG), which is known to be one of the constituents of the kanamycin molecule and a metabolite of Bacillus sp., was almost completely overcome by glucosamine and N-acetylglucosamine in Staphylococcus aureus but scarcely affected by D-glucose and D-fructose. The antibiotic did not inhibit the incorporation of [14C]glucosamine and [3H]N-acetylglucosamine into the acid-insoluble fraction, but rather enhanced the incorporation of [14C]glucosamine. On the other hand, it inhibited the incorporation of D-[14C]fructose into the cell wall fraction but hardly affected the incorporation of D-[14C]fructose into the acid-insoluble fraction in the presence of pencillin G. Based on these results, it is suggested that the site of primary action of 3-AG is the formation of glucosamine-6-phosphate from D-fructose-6-phosphate, which is catalyzed by glucosamine synthetase [EC 2.6.1.16].
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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 ╳
