Butirosin
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| Category | Antibiotics |
| Catalog number | BBF-00592 |
| CAS | 12772-35-9 |
| Molecular Weight | 555.57 |
| Molecular Formula | C21H41N5O12 |
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Description
Butirosin 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
| Related CAS | 51022-98-1 (disulfate) |
| Synonyms | Ambutyrosin |
| IUPAC Name | (2R)-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-[(2R,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-NUOYRARPSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria |
| Boiling Point | 1186.7°C at 760 mmHg |
Reference Reading
1. 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.
2. 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.
3. Butirosin-biosynthetic gene cluster from Bacillus circulans
Y Ota, H Tamegai, F Kudo, H Kuriki, A Koike-Takeshita, T Eguchi, K Kakinuma J Antibiot (Tokyo). 2000 Oct;53(10):1158-67. doi: 10.7164/antibiotics.53.1158.
Butirosin is an interesting 2-deoxystreptamine (DOS)-containing aminoglycoside antibiotic produced by non-actinomycete Bacilli. Recently we were successful in purification of 2-deoxy-scyllo-inosose synthase from butirosin-producer Bacillus circulans as the key enzyme for the biosynthesis of DOS, in cloning of the responsible gene (btrC), and in its overexpression in Escherichia coli. The present study involved gene-walking approach, which allowed us to find a gene cluster around btrC. The function of each gene was further investigated by gene disruption, and the disruptants of btrB, btrC, btrD and btrM showed no antibiotic producing activity. Therefore, the gene cluster found so far was determined to be a part of the butirosin biosynthetic gene cluster. Functions of some ORFs are also discussed in terms of butirosin biosynthesis on the basis of database search.
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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 ╳
