Butirosin sulfate

For research use only. Not for therapeutic Use.

  • CAT Number: I023852
  • CAS Number: 51022-98-1
  • Molecular Formula: C21H45N5O20S2
  • Molecular Weight: 751.7
  • Purity: 98%
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Butirosin sulfate (Cat.No:I023852) is a water-soluble aminoglycosidic antibiotic complex isolated from fermentation filtrates of Bacillus circulans. Two components (A and B) have been separated from the complex. Both are active against many gram-positive and some gram-negative bacteria.


Catalog Number I023852
CAS Number 51022-98-1
Synonyms

Butirosin sulfate; CI642; CI 642; CI-642

Molecular Formula C21H45N5O20S2
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
IUPAC Name 4-amino-N-((1R,2S,3R,4R,5S)-5-amino-4-(((2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-hydroxycyclohexyl)-2-hydroxybutanamide bis(sulfate) dihydrate
InChI InChI=1S/C21H41N5O12.2H2O4S.2H2O/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;2*1-5(2,3)4;;/h6-18,20-21,27-33H,1-5,22-25H2,(H,26,34);2*(H2,1,2,3,4);2*1H2/t6-,7+,8?,9+,10+,11+,12-,13+,14?,15+,16+,17+,18+,20+,21-;;;;/m0..../s1
InChIKey IUQWHBUMCWSQIM-OXNIXSIASA-N
SMILES NCCC(C(N[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O)O[C@@H]2O[C@@H](C([C@H]2O)O)CO)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3N)O)O)CN)N)=O)O.OS(=O)(O)=O.OS(=O)(O)=O.O.O
Reference

1: Ota Y, Tamegai H, Kudo F, Kuriki H, Koike-Takeshita A, Eguchi T, Kakinuma K. Butirosin-biosynthetic gene cluster from Bacillus circulans. J Antibiot (Tokyo). 2000 Oct;53(10):1158-67. doi: 10.7164/antibiotics.53.1158. PMID: 11132962.
2: Takeishi R, Kudo F, Numakura M, Eguchi T. Epimerization at C-3” in butirosin biosynthesis by an NAD(+) -dependent dehydrogenase BtrE and an NADPH-dependent reductase BtrF. Chembiochem. 2015 Feb 9;16(3):487-95. doi: 10.1002/cbic.201402612. Epub 2015 Jan 19. PMID: 25600434.
3: Dowding JE. Susceptibility to butirosin and neomycin B in Bacillus circulans, the butirosin-producing organism. J Gen Microbiol. 1979 Dec;115(2):385-9. doi: 10.1099/00221287-115-2-385. PMID: 93616.
4: Kudo F, Eguchi T. Biosynthetic enzymes for the aminoglycosides butirosin and neomycin. Methods Enzymol. 2009;459:493-519. doi: 10.1016/S0076-6879(09)04620-5. PMID: 19362652.
5: DiGiammarino EL, Draker KA, Wright GD, Serpersu EH. Solution studies of isepamicin and conformational comparisons between isepamicin and butirosin A when bound to an aminoglycoside 6′-N-acetyltransferase determined by NMR spectroscopy. Biochemistry. 1998 Mar 17;37(11):3638-44. doi: 10.1021/bi972778b. PMID: 9521682.
6: Llewellyn NM, Li Y, Spencer JB. Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain. Chem Biol. 2007 Apr;14(4):379-86. doi: 10.1016/j.chembiol.2007.02.005. PMID: 17462573.
7: Kudo F, Fujii T, Kinoshita S, Eguchi T. Unique O-ribosylation in the biosynthesis of butirosin. Bioorg Med Chem. 2007 Jul 1;15(13):4360-8. doi: 10.1016/j.bmc.2007.04.040. Epub 2007 Apr 25. PMID: 17482823.
8: Heifetz CL, Chodubski JA, Pearson IA, Silverman CA, Fisher MW. Butirosin compared with gentamicin in vitro and in vivo. Antimicrob Agents Chemother. 1974 Aug;6(2):124-35. doi: 10.1128/aac.6.2.124. PMID: 15828182; PMCID: PMC444617.
9: Aubert-Pivert E, el-Samaraie A, von Döhren H. A 4-amino-2-hydroxybutyrate activating enzyme from butirosin-producing Bacillus circulans. Biochem Biophys Res Commun. 1993 Dec 30;197(3):1334-9. doi: 10.1006/bbrc.1993.2623. PMID: 7506542.
10: Takeda K, Kinumaki A, Hayasaka H, Yamaguchi T, Ito Y. Mutational biosynthesis of butirosin analogs. II. 3′, 4′-Dideoxy-6′-N-methylbutirosins, new semisynthetic aminoglycosides. J Antibiot (Tokyo). 1978 Oct;31(10):1031-8. doi: 10.7164/antibiotics.31.1031. PMID: 81823.

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