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Merck

11702

Bacitracin

from Bacillus licheniformis, ≥65 IU/mg

Synonym(s):

Altracin, Bacitracin A

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About This Item

Empirical Formula (Hill Notation):
C66H103N17O16S
CAS Number:
1405-87-4
Molecular Weight:
1422.69
NACRES:
NA.85
PubChem Substance ID:
57646949
UNSPSC Code:
51282002
EC Number:
215-786-2
MDL number:
MFCD00062640

Product Name

Bacitracin, from Bacillus licheniformis, ≥65 IU/mg

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

InChI key

CLKOFPXJLQSYAH-RNHDWVCBSA-N

SMILES string

[H]N1[C@@H](Cc2cnc[nH]2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)C3CSC(=N3)C(N)C(C)CC)[C@@H](C)CC)C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](Cc4ccccc4)C1=O

biological source

Bacillus licheniformis

form

powder

specific activity

≥65 IU/mg

color

white to pale buff

antibiotic activity spectrum

Gram-positive bacteria

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

Quality Level

200

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Application

Bacitracin is used to study disruption of bacterial cell wall synthesis at the level of peptidoglycan biosynthesis and isoprenyl metabolism. It is also used to study the biosynthesis of sterols and squalene.
Bacitracin has been used:
  • as a protease inhibitor
  • as a control antibiotic
  • for the calibration in size exclusion chromatography

Biochem/physiol Actions

Bacitracin has been shown to decrease vancomycin-resistant Enterococcus faecium population in intestine.
Bacitracin is a peptide antibiotic.
Antimicrobial spectrum: Gram-positive bacteria.
Mode of Action: Inhibits bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphate.

General description

Chemical structure: peptide

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Moisture sensitive. Keep in a dry place.

Packaging

5G, 25 G

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000504461
0000504461
0000368617
0000368618
0000354954

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Oral Bacitracin: A Consideration for Suppression of Intestinal Vancomycin-Resistant Enterococci (VRE) and for VRE Bacteremia From an Apparent Gastrointestinal Tract Source.
Truc T Tran et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 60(11), 1726-1728 (2015-02-24)
Ashwantha Kumar Enjapoori et al.
Genome biology and evolution, 6(10), 2754-2773 (2014-09-24)
Monotremes (platypus and echidna) are the descendants of the oldest ancestor of all extant mammals distinguished from other mammals by mode of reproduction. Monotremes lay eggs following a short gestation period and after an even briefer incubation period, altricial hatchlings
Anthony W Kingston et al.
Molecular microbiology, 93(1), 37-49 (2014-05-09)
Heptaprenyl diphosphate (C35 -PP) is an isoprenoid intermediate in the synthesis of both menaquinone and the sesquarterpenoids. We demonstrate that inactivation of ytpB, encoding a C35 -PP utilizing enzyme required for sesquarterpenoid synthesis, leads to an increased sensitivity to bacitracin
Hiromasa Tsuda et al.
Antimicrobial agents and chemotherapy, 46(12), 3756-3764 (2002-11-19)
Streptococcus mutans is resistant to bacitracin, which is a peptide antibiotic produced by certain species of Bacillus. The purpose of this study was to clarify the bacitracin resistance mechanism of S. mutans. We cloned and sequenced two S. mutans loci
Kazuhiko Nakano et al.
Nature communications, 2, 485-485 (2011-09-29)
Although several risk factors for stroke have been identified, one-third remain unexplained. Here we show that infection with Streptococcus mutans expressing collagen-binding protein (CBP) is a potential risk factor for haemorrhagic stroke. Infection with serotype k S. mutans, but not
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