Bacitracin F

Bacitracin F

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Bacitracin F
Category Antibiotics
Catalog number BBF-04106
CAS 22601-63-4
Molecular Weight 1419.68
Molecular Formula C66H98N16O17S
Purity >95%

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Description

Bacitracin F is a major Bacitracin analog, a peptide antibiotic used as an inhibitor of protein disulfide isomerase (PDI). It is isolated from Bacillus.

Specification

Synonyms Bacitracin H3; N2-[N-[[2-[(S)-2-Methylbutanoyl]thiazol-4-yl]carbonyl]-L-Leu-D-Glu-L-Ile-]cyclo(L-Lys-D-Orn-L-Ile-D-Phe-L-His-D-Asp-L-Asn-)
Storage Store at 2-8°C
IUPAC Name 5-[[1-[[3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-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]-4-[[4-methyl-2-[[2-(2-methylbutanoyl)-1,3-thiazole-4-carbonyl]amino]pentanoyl]amino]-5-oxopentanoic acid
Canonical 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)C2=CSC(=N2)C(=O)C(C)CC)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
InChI InChI=1S/C66H98N16O17S/c1-9-35(6)52(82-58(92)42(22-23-50(84)85)73-59(93)43(26-34(4)5)75-63(97)48-32-100-66(80-48)54(88)37(8)11-3)64(98)74-40-20-15-16-25-70-55(89)46(29-49(68)83)77-62(96)47(30-51(86)87)78-61(95)45(28-39-31-69-33-71-39)76-60(94)44(27-38-18-13-12-14-19-38)79-65(99)53(36(7)10-2)81-57(91)41(21-17-24-67)72-56(40)90/h12-14,18-19,31-37,40-47,52-53H,9-11,15-17,20-30,67H2,1-8H3,(H2,68,83)(H,69,71)(H,70,89)(H,72,90)(H,73,93)(H,74,98)(H,75,97)(H,76,94)(H,77,96)(H,78,95)(H,79,99)(H,81,91)(H,82,92)(H,84,85)(H,86,87)
InChI Key FCLQHQCOKGKLHR-UHFFFAOYSA-N
Source Bacillus subtilis var Tracy

Properties

Appearance Pale Yellow Solid
Melting Point >265°C
Density 1.3±0.1 g/cm3
Solubility Soluble in Aqueous Acid, Acidic Methanol, Methanol

Reference Reading

1. [Sporulation in Bacillus licheniformis during altered bacitracin synthesis]
B V Tiaglov,A N Rozov,A A Lukin,V I Permogorov Antibiotiki . 1983 Jul;28(7):494-7.
Sporulation in different strains of Bacillus licheniformis, 10716 and 1001 in connection with changes in synthesis of bacitracin was studied. It was shown that the sporulation efficiency did not depend on the synthesis of the antibiotic: in some strains with low potency for the antibiotic production, the sporulation level was lowered, while in the others, it was not lowered. Moreover, normal sporulation was also observed, when the synthesis of bacitracin was inhibited. Therefore, it is suggested that there is no correlation between the sporulation and antibiotic production.
2. Sequencing of bacitracin A and related minor components by liquid chromatography/electrospray ionization ion trap tandem mass spectrometry
Cindy Govaerts,Chunlan Li,Jennifer Orwa,Jos Hoogmartens,Eugène Roets,Ann Van Schepdael,Erwin Adams Rapid Commun Mass Spectrom . 2003;17(12):1366-1379. doi: 10.1002/rcm.1058.
A selective reversed-phase liquid chromatography/mass spectrometry (LC/MS(n)) method is described for the characterization of related compounds in commercial bacitracin samples. Mass spectral data for these polypeptide antibiotics were acquired on a LCQ ion trap mass spectrometer equipped with an electrospray ionization probe operated in the positive and negative ion mode. The LCQ ion trap is ideally suited for the sequencing of those linear side-chain cyclized peptides because it provides on-line LC/MS(n) capability. Using this method bacitracin A, 1-epibacitracin A, bacitracins B(1), B(2), B(3) and bacitracin F were sequenced and previous sequencing was confirmed. Bacitracins C(1), C(2), C(3), D, H(2) and H(3) were resolved chromatographically and their ring portion was sequenced for the first time. Four components not described in the literature (1-epibacitracin B(1), 1-epibacitracin B(2), 1-epibacitracin C(1) and H(4)) were sequenced completely for the first time. The main advantage of this hyphenated LC/MS(n) technique is the characterization of the related substances without time-consuming isolation and purification procedures.
3. Isolation of bacitracins A and F by high-speed counter-current chromatography
H Oka,M Suzuki,Y Ikai,Y Yamazaki,K Harada,H Nakazawa,Y Ito J Chromatogr . 1991 Jan 18;538(1):203-12. doi: 10.1016/s0021-9673(01)91638-3.
The major components of bacitracin were separated and purified using high-speed counter-current chromatography (HSCCC). A systematic search for optimum two-phase solvent systems resulted in two systems: chloroform-ethanol-methanol-water (5:3:3:4) and chloroform-ethanol-water (5:4:3). These were selected based on the determination of the partition coefficients of all the components and the settling time of the phases. HSCCC with these solvent systems separated two components, bacitracins A and F. Improvements in the flow-cell arrangement eliminated noise in detection, making in-line monitoring possible. A tandem mass spectrometric technique was used to characterize the isolated components.
4. Further evidence for the presence of a thiazoline ring in the isoleucylcysteine dipeptide intermediate in bacitracin biosynthesis
K Shimura,H Ishihara FEBS Lett . 1988 Jan 4;226(2):319-23. doi: 10.1016/0014-5793(88)81447-9.
Isoleucylcysteine dipeptide, a first intermediate peptide in bacitracin biosynthesis, was liberated from the enzyme protein and oxidized with manganese dioxide in dimethylsulfoxide. The resulting oxidation product was identified by thin-layer chromatography as 2-(2-methyl-l-oxobutyl)-thiazole-4-carboxylic acid which has been isolated from the hydrolysate of bacitracin F. This result shows that the intermediate dipeptide contains a thiazoline ring, and that the thiazoline ring is synthesized at the dipeptide stage in the process of peptide chain elongation in bacitracin biosynthesis. Improbability of non-enzymatic dehydrative cyclization of the dipeptide is discussed.

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