Gageostatin A
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| Category | Bioactive by-products |
| Catalog number | BBF-04340 |
| CAS | |
| Molecular Weight | 1040.33 |
| Molecular Formula | C52H93N7O14 |
| Purity | ≥90% |
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Description
An antimicrobial peptide (AMP) isolated from a marine strain of bacillus subtilis. It is a linear lipopeptide composed of 7 peptides. It has shown initial bioactivity against pathogenic fungi, gram-positive and gram-negative bacteria, and cancer cell lines.
Specification
| Synonyms | Unk-Glu-Leu-Leu-D-Val-Asp-Leu-Leu-OH; N-[(3R)-3-Hydroxy-11-methyltridecanoyl]-L-α-glutamyl-L-leucyl-L-leucyl-D-valyl-L-α-asparagyl-L-leucyl-L-leucine |
| Sequence | ELLVDLL |
| IUPAC Name | (2S)-2-[[(2S)-2-[[(2S)-3-carboxy-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-carboxy-2-[[(3R)-3-hydroxy-11-methyltridecanoyl]amino]butanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoic acid |
| Canonical SMILES | CCC(C)CCCCCCCC(CC(=O)NC(CCC(=O)O)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CC(=O)O)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)O)O |
| InChI | InChI=1S/C52H93N7O14/c1-13-34(12)19-17-15-14-16-18-20-35(60)27-42(61)53-36(21-22-43(62)63)46(66)54-37(23-29(2)3)47(67)56-39(25-31(6)7)50(70)59-45(33(10)11)51(71)57-40(28-44(64)65)49(69)55-38(24-30(4)5)48(68)58-41(52(72)73)26-32(8)9/h29-41,45,60H,13-28H2,1-12H3,(H,53,61)(H,54,66)(H,55,69)(H,56,67)(H,57,71)(H,58,68)(H,59,70)(H,62,63)(H,64,65)(H,72,73)/t34?,35-,36+,37+,38+,39+,40+,41+,45-/m1/s1 |
| InChI Key | ASKJUGVPESKJDD-YNEMRZIYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Fungi |
| Boiling Point | 1265.9±65.0°C at 760 mmHg |
| Density | 1.1±0.1 g/cm3 |
Reference Reading
1. Gageostatins A-C, antimicrobial linear lipopeptides from a marine Bacillus subtilis
Jong-Seok Lee, Hee Jae Shin, Hyi-Seung Lee, Min Ah Lee, Yeon-Ju Lee, Fakir Shahidullah Tareq Mar Drugs . 2014 Jan 31;12(2):871-85. doi: 10.3390/md12020871.
Concerning the requirements of effective drug candidates to combat against high rising multidrug resistant pathogens, we isolated three new linear lipopeptides, gageostatins A-C (1-3), consisting of hepta-peptides and new 3-β-hydroxy fatty acids from the fermentation broth of a marine-derived bacterium Bacillus subtilis. Their structures were elucidated by analyzing a combination of extensive 1D, 2D NMR spectroscopic data and high resolution ESIMS data. Fatty acids, namely 3-β-hydroxy-11-methyltridecanoic and 3-β-hydroxy-9,11-dimethyltridecanoic acids were characterized in lipopeptides 1 and 2, respectively, whereas an unsaturated fatty acid (E)-7,9-dimethylundec-2-enoic acid was assigned in 3. The 3R configuration of the stereocenter of 3-β-hydroxy fatty acids in 1 and 2 was established by Mosher's MTPA method. The absolute stereochemistry of amino acid residues in 1-3 was ascertained by acid hydrolysis followed by Marfey's derivatization studies. Gageostatins 1-3 exhibited good antifungal activities with MICs values of 4-32 µg/mL when tested against pathogenic fungi (R. solani, B. cinerea and C. acutatum) and moderate antibacterial activity against bacteria (B. subtilis, S. aeureus, S. typhi and P. aeruginosa) with MICs values of 8-64 µg/mL. Futhermore, gageostatins 1-3 displayed cytotoxicity against six human cancer cell lines with GI₅₀ values of 4.6-19.6 µg/mL. It is also noteworthy that mixed compounds 1+2 displayed better antifungal and cytotoxic activities than individuals.
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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 ╳
