3-Trehalosamine
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| Category | Antibiotics |
| Catalog number | BBF-02706 |
| CAS | 75060-25-2 |
| Molecular Weight | 341.31 |
| Molecular Formula | C12H23NO10 |
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Description
3-Trehalosamine is originally isolated from Nocardiopsis trehalosis sp. nov. NRRL 12026. It has a weak anti-Gram-positive bacteria effect.
Specification
| Synonyms | hexopyranosyl 3-amino-3-deoxyhexopyranoside; 3-Amino-3-deoxy-alpha-D-glucopyranosyl-alpha-D-glucopyranoside |
| IUPAC Name | (2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol |
| Canonical SMILES | C(C1C(C(C(C(O1)OC2C(C(C(C(O2)CO)O)O)O)O)N)O)O |
| InChI | InChI=1S/C12H23NO10/c13-5-6(16)3(1-14)21-11(8(5)18)23-12-10(20)9(19)7(17)4(2-15)22-12/h3-12,14-20H,1-2,13H2/t3-,4-,5+,6-,7-,8-,9+,10-,11-,12-/m1/s1 |
| InChI Key | OHNBYBTUSOVUMK-PNKJYEMWSA-N |
Properties
| Appearance | White Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 200°C |
Reference Reading
1. Preparation of 3-amino-3-deoxy derivatives of trehalose and sucrose and their activities
N Asano, K Katayama, M Takeuchi, T Furumoto, Y Kameda, K Matsui J Antibiot (Tokyo). 1989 Apr;42(4):585-90. doi: 10.7164/antibiotics.42.585.
The 3-keto derivatives of trehalose and sucrose respectively were prepared by a one-step enzymatic route using D-glucoside 3-dehydrogenase from Flavobacterium saccharophilum. Reductive amination of 3-ketotrehalose with ammonium acetate and sodium cyanoborohydride gave three compounds, 3-amino-3-deoxy-alpha-D-allopyranosyl alpha-D-glucopyranoside, 3-amino-3-deoxy-alpha-D-glucopyranosyl alpha-D-glucopyranoside (3-trehalosamine) and 3-amino-3-deoxy-alpha-D-mannopyranosyl alpha-D-glucopyranoside. From the reductive amination of 3-ketosucrose, 3-amino-3-deoxy-alpha-D-allopyranosyl beta-D-fructofuranoside and 3-amino-3-deoxy-alpha-D-glucopyranosyl beta-D-fructofuranoside were obtained. The antibiotic and glycohydrolase inhibitory activities of these 3-amino-3-deoxy derivatives were determined.
2. Diverse Synthesis of Natural Trehalosamines and Synthetic 1,1'-Disaccharide Aminoglycosides
Yen-Chu Lu, Soumik Mondal, Ching-Chi Wang, Chun-Hung Lin, Kwok-Kong Tony Mong Chembiochem. 2019 Jan 18;20(2):287-294. doi: 10.1002/cbic.201800656. Epub 2018 Dec 20.
A general strategy for the diverse synthesis of ten disaccharide aminoglycosides, including natural 2-trehalosamine (1), 3-trehalosamine (2), 4-trehalosamine (3), and neotrehalosyl 3,3'-diamine (8) and synthetic aminoglycosides 4-7, 9, and 10, has been developed. The aminoglycoside compounds feature different anomeric configurations and numbers of amino groups. The key step for the synthesis was the glycosylation coupling of a stereodirecting donor with a configuration-stable TMS glycoside acceptor. Either the donor or acceptor could be substituted with an azido group. The aminoglycosides prepared in the present study were characterized by 1D and 2D NMR spectroscopy.
3. A novel trehalosamine isolated from Bacillus amyloliquefaciens and its antibacterial activities
Ying Wang, Bo Zhao, Yaping Liu, Linjing Mao, Xuanming Zhang, Wu Meng, Kechun Liu, Jie Chu AMB Express. 2020 Jan 14;10(1):6. doi: 10.1186/s13568-019-0943-x.
Bacillus amyloliquefaciens has been widely used as a probiotic in the field of biological control,and its antibacterial compounds plays an important role in the prevention and control of plant, livestock and poultry diseases. It has the advantages of green, safe and efficiency. This study aims to separate and purify active ingredient from Bacillus amyloliquefaciens GN59 and study its antibacterial activity. A novel compound was isolated from GN59 by column chromatography on silica gel and HPLC purification. The chemical structure was identified as α-D-glucopyranosyl-(1 → 1')-3'-amino-3'-deoxy-β-D-glucopyranoside (a,β-3-trehalosamine) on the basis of spectroscopic analysis. This is the first report about a,β-3-trehalosamine isolated from biological resources on an antibiotic activity against pathogenic bacterium. The 3'-neotrehalosamine displayed antibacterial activity across a broad spectrum of microorganisms, including different gram-positive and gram-negative bacteria, with minimal inhibitory concentration (MIC) values ranging from 0.5 to 0.7 mg/mL. The results indicated that the 3'-neotrehalosamine from GN59 might be a potential candidate for bactericide.
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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 ╳
