Butirosin B
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| Category | Bioactive by-products |
| Catalog number | BBF-00191 |
| CAS | 34291-03-7 |
| Molecular Weight | 555.57 |
| Molecular Formula | C21H41N5O12 |
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Description
Butirosin B 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 B |
| 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,4S,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-HBYCGHPUSA-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 | 172-173°C(dec.) |
| Density | 1.58 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, water |
Reference Reading
1. Unique O-ribosylation in the biosynthesis of butirosin
Fumitaka Kudo, Takuya Fujii, Shunsuke Kinoshita, Tadashi Eguchi Bioorg Med Chem. 2007 Jul 1;15(13):4360-8. doi: 10.1016/j.bmc.2007.04.040. 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.
2. Epimerization at C-3'' in butirosin biosynthesis by an NAD(+) -dependent dehydrogenase BtrE and an NADPH-dependent reductase BtrF
Ryohei Takeishi, Fumitaka Kudo, Mario Numakura, Tadashi Eguchi Chembiochem. 2015 Feb 9;16(3):487-95. doi: 10.1002/cbic.201402612. Epub 2015 Jan 19.
Butirosin is an aminoglycoside antibiotic consisting two epimers at C-3'' of ribostamycin/xylostasin with a unique 4-amino-2-hydroxybutyrate moiety at C-1 of the aminocyclitol 2-deoxystreptamine (2DOS). To date, most of the enzymes encoded in the biosynthetic gene cluster for butirosin, from the producing strain Bacillus circulans, have been characterized. A few unknown functional proteins, including nicotinamide adenine dinucleotide cofactor-dependent dehydrogenase/reductase (BtrE and BtrF), are supposed to be involved in the epimerization at C-3'' of butirosin B/ribostamycin but remain to be characterized. Herein, the conversion of ribostamycin to xylsostasin by BtrE and BtrF in the presence of NAD(+) and NADPH was demonstrated. BtrE oxidized the C-3'' of ribostamycin with NAD(+) to yield 3''-oxoribostamycin. BtrF then reduced the generated 3''-oxoribostamycin with NADPH to produce xylostasin. This reaction step was the last piece of butirosin biosynthesis to be described.
3. Extended sequence and functional analysis of the butirosin biosynthetic gene cluster in Bacillus circulans SANK 72073
Fumitaka Kudo, Mario Numakura, Hideyuki Tamegai, Hideki Yamamoto, Tadashi Eguchi, Katsumi Kakinuma J Antibiot (Tokyo). 2005 Jun;58(6):373-9. doi: 10.1038/ja.2005.47.
Butirosin produced by Bacillus circulans is among the clinically important 2-deoxystreptamine containing aminoglycoside antibiotics and its unique structure is found in (S)-4-amino-2-hydroxyburyric acid substituted at C-1 of 2-deoxystreptamine. Recently, the key part of the butirosin biosynthetic gene cluster has been identified from Bacillus circulans SANK 72073, however the whole gene for the biosynthesis awaited for identification. In the present study, we undertook extended analysis of the butirosin biosynthetic gene cluster and found nine additional open reading flames (ORFs), btrQ, btrR1, btrR2, btrT, btrU, btrV, btrW, btrX and orf1 in the cluster. In addition, we constructed disruption mutants of btrR1 and btrP-V, and found that the btr genes (ca. 24Kb) between btrR1 and btrP-V are at least required for the butirosin biosynthesis.
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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 ╳
