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Bacitracin

Peptide antibiotic CAS# 1405-87-4

Bacitracin

Catalog No. BCC4632----Order now to get a substantial discount!

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Chemical structure

Bacitracin

3D structure

Chemical Properties of Bacitracin

Cas No. 1405-87-4 SDF Download SDF
PubChem ID 10909430 Appearance Powder
Formula C65H101N17O16S M.Wt 1408.7
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Bacitracin A; Baciguent; Bacitracin A2a
Solubility H2O : 50 mg/mL (35.14 mM; Need ultrasonic)
Sequence Unk-Leu-D-Glu-Ile-Lys(1)-D-Orn-Ile-D-Phe-His-D-Asp-Asn
Chemical Name (4R)-4-[[(2S)-2-[[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
SMILES CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C2CSC(=N2)C(C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
Standard InChIKey CLKOFPXJLQSYAH-ABRJDSQDSA-N
Standard InChI InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

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Background on Bacitracin

Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy, which disrupts both gram positive and gram negative bacteria by interfering with cell wall and peptidoglycan syn

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References on Bacitracin

Multilevel selection of bcrABDR-mediated bacitracin resistance in Enterococcus faecalis from chicken farms.[Pubmed:27731342]

Sci Rep. 2016 Oct 12;6:34895.

In this study we isolated 109 Enterococcus faecalis from chicken faecal samples in 6 provinces of China to investigate the prevalence and transmission mechanism of the Bacitracin resistance locus bcrABDR in E. faecalis. Thirty-seven bcrABDR-positive E. faecalis were detected with 26 different PFGE clusters. The MLST of 14 positive strains belonged to ST16 and we also detected three new sequence types. S1-PFGE analysis indicated that the locus was located on plasmids presenting different sizes, with the most prevalent size being ~50 kb (13/37). Sequence analysis revealed that 17 out of the 37 strains harbored a 5400-bp central region, in which locus bcrABDR was bracketed by two ISEnfa1 of the same orientation. Two types of bcrABDR alleles, differing in around 10% of their sequence were found. In silico analysis showed that bcrABDR is present in a variety of bacteria including the chicken commensal Enterococcus cecorum. Our results indicate that the use of Bacitracin at farms might trigger the emergence and spread of the Bacitracin resistance determinant bcrABDR among human bacterial pathogens. The finding of bcrABDR in the chicken commensal E. cecorum indicates that farm animals microbiota can be an important reservoir of resistance genes with relevance for human health.

Immobilizing bacitracin on titanium for prophylaxis of infections and for improving osteoinductivity: An in vivo study.[Pubmed:27914255]

Colloids Surf B Biointerfaces. 2017 Feb 1;150:183-191.

Bacitracin immobilized on the titanium (Ti) surface significantly improves anti-bacterial activity and biocompatibility in vitro. In the current study, we investigated the biologic performance (bactericidal effect and bone-implant integration) of Bacitracin-modified Ti in vivo. A rat osteomyelitis model with femoral medullary cavity placement of Ti rods was employed to analyze the prophylactic effect of Bacitracin-modified Ti (Ti-BC). Thirty-six female Sprague Dawley (SD) rats were used to establish the Ti implant-associated infection. The Ti and Ti-BC rods were incubated with and without Staphylococcus aureus to mimic the contaminated Ti rod and were implanted into the medullary cavity of the left femur, and sterile Ti rods were used as the blank control. After 3 weeks, the bone pathology was evaluated using X-ray and micro-computed tomography (micro-CT) analysis. For the investigation of the Ti-BC implant osseointegration in vivo, fifteen SD rats were divided into three groups (N=5), namely Ti, Ti-dopamine immobilized (Ti-DOPA), and Ti-BC. Ti rods were implanted into the left femoral cavity and micro-CT and histological evaluation was conducted after 12 weeks. The in vivo study indicated that Ti-immobilized Bacitracin owned the prophylaxis potential for the infection associated with the Ti implants and allowed for the osseointegration. Thus, the multiple biofunctionalized Ti implants could be realized via immobilization of Bacitracin, making them promising candidates for preventing the Ti implant-associated infections while retaining the osseointegration effects.

Untangling the transcription regulatory network of the bacitracin synthase operon in Bacillus licheniformis DW2.[Pubmed:28279714]

Res Microbiol. 2017 Jul - Aug;168(6):515-523.

The Bacitracin synthetase gene cluster in Bacillus licheniformis DW2 is composed of the bacABC operon encoding a non-ribosomal peptide synthetase and bacT encoding a thioesterase. Although the Bacitracin gene cluster has been well studied, little is known about how this gene cluster is regulated. This study provides insight into how the transcription factors Spo0A and AbrB regulate Bacitracin biosynthesis. Deletion of spo0A resulted in drastically reduced expression of bacA and bacT, and subsequently Bacitracin production. On the other hand, the expression of bacA and bacT increased significantly in B. licheniformis DW2DeltaabrB and DW2Delta0ADeltaabrB compared to the wild-type strain DW2. The Bacitracin yields on cell numbers (U/CFU) in DW2DeltaabrB and DW2Delta0A/pHY300-0A-sad67 were 17.5% and 14.9% higher than that of the wild-type strain. An electrophoretic mobility shift assay (EMSA) further confirmed that AbrB could directly bind to the promoter regions of bacA and bacT. These results indicate that AbrB acts as a repressor of Bacitracin biosynthesis by inhibiting bacA and bacT expression, while Spo0A indirectly promotes Bacitracin biosynthesis by repressing abrB expression.

Understanding the mechanisms of zinc bacitracin and avilamycin on animal production: linking gut microbiota and growth performance in chickens.[Pubmed:28243710]

Appl Microbiol Biotechnol. 2017 Jun;101(11):4547-4559.

Unravelling the mechanisms of how antibiotics influence growth performance through changes in gut microbiota can lead to the identification of highly productive microbiota in animal production. Here we investigated the effect of zinc Bacitracin and avilamycin on growth performance and caecal microbiota in chickens and analysed associations between individual bacteria and growth performance. Two trials were undertaken; each used 96 individually caged 15-day-old Cobb broilers. Trial 1 had a control group (n = 48) and a zinc Bacitracin (50 ppm) treatment group (n = 48). Trial 2 had a control group (n = 48) and an avilamycin (15 ppm) treatment group (n = 48). Chicken growth performance was evaluated over a 10-day period, and caecal microbiota was characterised by sequencing of bacterial 16S rRNA gene amplicons. Avilamycin produced no effect on growth performance and exhibited little significant disturbance of the microbiota structure. However, zinc Bacitracin reduced the feed conversion ratio (FCR) in treated birds, changed the composition and increased the diversity of their caecal microbiota by reducing dominant species. Avilamycin only produced minor reductions in the abundance of two microbial taxa, whereas zinc Bacitracin produced relatively large shifts in a number of taxa, primarily Lactobacillus species. Also, a number of phylotypes closely related to lactobacilli species were positively or negatively correlated with FCR values, suggesting contrasting effects of Lactobacillus spp. on chicken growth performance. By harnessing such bacteria, it may be possible to develop high-productivity strategies in poultry that rely on the use of probiotics and less on in-feed antibiotics.

Description

Bacitracin is a polypeptide antibiotic used for staphylococcal infections. Bacitracin functions as an inhibitor of cell wall biosynthesis through its binding to the undecaprenyl pyrophosphate. The combination of bacitracin with other antibiotics has been efficient to be used as a topical agent.

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