Glidobactin B
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| Category | Antibiotics |
| Catalog number | BBF-01248 |
| CAS | 108351-51-5 |
| Molecular Weight | 546.70 |
| Molecular Formula | C29H46N4O6 |
| Purity | ≥95% |
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Description
It is produced by the strain of Polyangium brachysporum sp. No. K481-B-101. It is an anti-tumor antibiotic. It has the activity against pathogenic fungi and yeast, the activity of Glidobactin C is the strongest. It also extends the survival of mice inoculated with leukemia P388 cells.
Specification
| Synonyms | Antibiotic BU-2867TB; BU-2867TB; 2,4,8-Tetradecatrienamide, N-(2-hydroxy-1-(((10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)amino)carbonyl)propyl)-, (5S-(3E,5R*,8R*(1R*(2E,4E,8E),2S*),10R*))- |
| IUPAC Name | (2E,4E,8E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]tetradeca-2,4,8-trienamide |
| Canonical SMILES | CCCCCC=CCCC=CC=CC(=O)NC(C(C)O)C(=O)NC1CC(CCNC(=O)C=CC(NC1=O)C)O |
| InChI | InChI=1S/C29H46N4O6/c1-4-5-6-7-8-9-10-11-12-13-14-15-26(37)33-27(22(3)34)29(39)32-24-20-23(35)18-19-30-25(36)17-16-21(2)31-28(24)38/h8-9,12-17,21-24,27,34-35H,4-7,10-11,18-20H2,1-3H3,(H,30,36)(H,31,38)(H,32,39)(H,33,37)/b9-8+,13-12+,15-14+,17-16-/t21-,22+,23-,24-,27-/m0/s1 |
| InChI Key | AZHZGGIJCMPFMJ-AECIEKQISA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi; Yeast |
| Boiling Point | 915.2 °C at 760 mmHg |
| Melting Point | 232-234 °C |
| Density | 1.15 g/cm3 |
| Solubility | Soluble in Methanol, DMSO, Ethanol; Fairly soluble in Ethyl Acetate, Acetonitrile, Chloroform; Insoluble in Water |
Reference Reading
1. Enzymatic formation of glidobactamine: a peptide nucleus of glidobactins A, B and C, new lipopeptide antitumor antibiotics
K Numata, M Oka, Y Nakakita, T Murakami, T Miyaki, M Konishi, T Oki, H Kawaguchi J Antibiot (Tokyo). 1988 Oct;41(10):1351-7. doi: 10.7164/antibiotics.41.1351.
Glidobactin deacylating activity was found in a bacterial strain of Pseudomonas sp. Glidobactamine, a key intermediate for acyl analogues of glidobactin, was isolated from the enzymatic degradation products of glidobactins after treatment using a column of fibrous active gel on which the cells of the Pseudomonas strain were immobilized. The chemical structure of glidobactamine was confirmed as the intact peptide moiety of glidobactins by chemical reformation of glidobactin A from glidobactamine and 2,4-dodecadienoic acid which is the constitutive fatty acid of glidobactin A.
2. Enhanced production of the minor components of glidobactins in Polyangium brachysporum
K Numata, T Murakami, M Oka, H Yamamoto, M Hatori, T Miyaki, T Oki, H Kawaguchi J Antibiot (Tokyo). 1988 Oct;41(10):1358-65. doi: 10.7164/antibiotics.41.1358.
Polyangium brachysporum sp. nov. strain ATCC 53080 produces a novel type of antifungal and antitumor antibiotic complex, glidobactins A, B and C. Enhanced production of minor components, glidobactins B and C, was achieved by medium modification. The addition of soybean oil or corn oil, which are rich in unsaturated C18 fatty acids, to the fermentation medium led to an increased production of components B and C. Productivity of component C was selectively enhanced by the addition of oleic acid-rich oils, olive oil and Tween 80 (polyoxyethylene sorbitan mono-oleate). Furthermore, precursing palmitoleate, linoleate and oleate permitted the direct biosynthesis of components A, B and C, respectively. The fermentation with 3% addition of an appropriate oil at initial time provided an optimal production of component B or C.
3. Glidobactins A, B and C, new antitumor antibiotics. II. Structure elucidation
M Oka, K Yaginuma, K Numata, M Konishi, T Oki, H Kawaguchi J Antibiot (Tokyo). 1988 Oct;41(10):1338-50. doi: 10.7164/antibiotics.41.1338.
The structures of new antitumor antibiotics, glidobactins A (Ia), B (Ib) and C (Ic) were elucidated by a combination of chemical and enzymatic degradations and spectral analyses. They have in common a cyclized tripeptide nucleus composed of L-threonine, 4(S)-amino-2(E)-pentenoic acid and erythro-4-hydroxy-L-lysine, and differ from each other in the unsaturated fatty acid moiety attached to the peptide.
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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 ╳
