Butirosin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00593 |
| CAS | 34291-02-6 |
| Molecular Weight | 555.57 |
| Molecular Formula | C21H41N5O12 |
| Purity | 95% |
Online Inquiry
Description
Butirosin A is an aminoglycoside antibiotic produced by acillus circulans. It has activity against gram-positive bacteria, negative bacteria, and mycobacteria. It is not cross-resistant to gentamicin, and has an effect on some kanamycin-resistant bacteria.
Specification
| Synonyms | Ambutyrosin A |
| Storage | 2-8ºC |
| IUPAC Name | (2S)-4-amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-hydroxycyclohexyl]-2-hydroxybutanamide |
| Canonical SMILES | C1C(C(C(C(C1NC(=O)C(CCN)O)O)OC2C(C(C(O2)CO)O)O)OC3C(C(C(C(O3)CN)O)O)N)N |
| InChI | InChI=1S/C21H41N5O12/c22-2-1-8(28)19(34)26-7-3-6(24)17(37-20-11(25)15(32)13(30)9(4-23)35-20)18(12(7)29)38-21-16(33)14(31)10(5-27)36-21/h6-18,20-21,27-33H,1-5,22-25H2,(H,26,34)/t6-,7+,8-,9+,10+,11+,12-,13+,14-,15+,16+,17+,18+,20+,21-/m0/s1 |
| InChI Key | XEQLFNPSYWZPOW-SVRMBHBBSA-N |
Properties
| Appearance | Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria |
| Boiling Point | 947.4°C at 760 mmHg |
| Melting Point | 166-168°C(dec.) |
| Density | 1.58 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, water |
Reference Reading
1.Characterization and mechanistic study of a radical SAM dehydrogenase in the biosynthesis of butirosin.
Yokoyama K1, Numakura M, Kudo F, Ohmori D, Eguchi T. J Am Chem Soc. 2007 Dec 12;129(49):15147-55. Epub 2007 Nov 15.
BtrN encoded in the butirosin biosynthetic gene cluster possesses a CXXXCXXC motif conserved within the radical S-adenosyl methionine (SAM) superfamily. Its gene disruption in the butirosin producer Bacillus circulans caused the interruption of the biosynthetic pathway between 2-deoxy-scyllo-inosamine (DOIA) and 2-deoxystreptamine (DOS). Further, in vitro assay of the overexpressed enzyme revealed that BtrN catalyzed the oxidation of DOIA under the strictly anaerobic conditions along with consumption of an equimolar amount of SAM to produce 5'-deoxyadenosine, methionine, and 3-amino-2,3-dideoxy-scyllo-inosose (amino-DOI). Kinetic analysis showed substrate inhibition by DOIA but not by SAM, which suggests that the reaction is the Ordered Bi Ter mechanism and that SAM is the first substrate and DOIA is the second. The BtrN reaction with [3-2H]DOIA generated nonlabeled, monodeuterated and dideuterated 5'-deoxyadenosines, while no deuterium was incorporated by incubation of nonlabeled DOIA in the deuterium oxide buffer.
2.Unique O-ribosylation in the biosynthesis of butirosin.
Kudo F1, Fujii T, Kinoshita S, Eguchi T. Bioorg Med Chem. 2007 Jul 1;15(13):4360-8. Epub 2007 Apr 25.
Using a comparative genetics approach, one or more of the BtrA, BtrL, BtrP, and BtrV proteins encoded in the butirosin biosynthetic gene cluster (btr) from Bacillus circulans SANK72073 were identified as being responsible for an O-ribosylation process leading to the formation of ribostamycin, a key intermediate in this, and related antibiotic biosynthetic pathways. Functional analysis of the recombinantly expressed proteins revealed that both BtrL and BtrP were responsible for the ribosylation of neamine, using 5-phosphoribosyl-1-diphosphate (PRPP) as the ribosyl donor. Further detailed analysis indicated that this process occurs via two discrete steps: with BtrL first catalyzing the phosphoribosylaion of neamine to form 5''-phosphoribostamycin, followed by a BtrP-catalyzed dephosphorylation to generate ribostamycin. To the best of our knowledge, this is the first time that the functional characterization of a glycosyltransferase from an aminoglycoside biosynthetic gene cluster has been reported.
3.Fluorescent HIV-1 Dimerization Initiation Site: design, properties, and use for ligand discovery.
Tam VK1, Kwong D, Tor Y. J Am Chem Soc. 2007 Mar 21;129(11):3257-66. Epub 2007 Feb 24.
The HIV-1 Dimerization Initiation Site (DIS) is an intriguing, yet underutilized, viral RNA target for potential antiretroviral therapy. To study the recognition features of this target and to provide a quantitative, rapid, and real-time tool for the discovery of new binders, a fluorescence-based assay has been constructed. It relies on strategic incorporation of 2-aminopurine, an isosteric fluorescent adenosine analogue, into short hairpin RNA constructs. These oligomers self-associate to form a kissing loop that thermally rearranges into a more stable extended duplex, thereby mimicking the association and structural features of the native RNA sequence. We demonstrate the ability of two fluorescent DIS constructs, DIS272(2AP) and DIS273(2AP), to report the binding of known DIS binders via changes in their emission intensity. Binding of aminoglycosides such as paromomycin to DIS272(2AP) results in significant fluorescence enhancement, while ligand binding to DIS273(2AP) results in fluorescence quenching.
Recommended Products
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-02614 | Nystatin | 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 ╳
