Stendomycin
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| Category | Antibiotics |
| Catalog number | BBF-03061 |
| CAS | 11006-78-3 |
| Molecular Weight | 1629.03 |
| Molecular Formula | C79H137N17O19 |
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Description
Stendomycin is an ester peptide antibiotic complex produced by Str. sp. It has anti-gram-positive bacteria, mycobacteria and fungi activity.
Specification
| IUPAC Name | N-[1-[[2-[[1-[[1-[[1-[[(Z)-1-[[6-butan-2-yl-12-(1-hydroxyethyl)-9-(hydroxymethyl)-22-methyl-3-(3-methyl-2-methylimino-1,3-diazinan-4-yl)-2,5,8,11,14,17,20-heptaoxo-15,18-di(propan-2-yl)-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]amino]-1-oxobut-2-en-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxobutan-2-yl]-N-methyl-1-(12-methyltridecanoyl)pyrrolidine-2-carboxamide |
| Canonical SMILES | CCC(C)C1C(=O)NC(C(=O)OC(C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CO)C(C)O)C(C)C)C(C)C)NC(=O)C(=CC)NC(=O)C(C)NC(=O)C(C(C)CC)NC(=O)C(C(C)C)NC(=O)CNC(=O)C(C(C)O)N(C)C(=O)C2CCCN2C(=O)CCCCCCCCCCC(C)C)C)C3CCNC(=NC)N3C |
| InChI | InChI=1S/C79H137N17O19/c1-21-45(12)60(90-69(105)57(42(6)7)86-55(100)39-82-76(112)65(49(16)99)95(20)77(113)54-34-32-38-96(54)56(101)35-31-29-27-25-24-26-28-30-33-41(4)5)72(108)83-47(14)66(102)84-51(23-3)67(103)92-63-50(17)115-78(114)64(53-36-37-81-79(80-18)94(53)19)93-73(109)61(46(13)22-2)89-68(104)52(40-97)85-74(110)62(48(15)98)91-71(107)59(44(10)11)87-70(106)58(43(8)9)88-75(63)111/h23,41-50,52-54,57-65,97-99H,21-22,24-40H2,1-20H3,(H,80,81)(H,82,112)(H,83,108)(H,84,102)(H,85,110)(H,86,100)(H,87,106)(H,88,111)(H,89,104)(H,90,105)(H,91,107)(H,92,103)(H,93,109)/b51-23- |
| InChI Key | ITDGBBBUDJYCDB-QACTWMCZSA-N |
Properties
| Appearance | Creamy Glassy Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi; mycobacteria |
| Solubility | Soluble in Methanol, Chloroform, Water, DMF |
Reference Reading
1. Stendomycin and Pantomycin Are Identical Natural Products: Preparation of a Functionalized Bioactive Analogue
Nikolaj L Villadsen, Bente K Hansen, Esben B Svenningsen, Katrine H Jørgensen, Thomas Tørring, Thomas B Poulsen J Org Chem. 2018 Jul 6;83(13):7303-7308. doi: 10.1021/acs.joc.8b00553. Epub 2018 May 18.
The natural products pantomycin and stendomycin were both reported as antimicrobial agents. We demonstrate by gene cluster analysis, LC-MS analysis, and isolation that these polypeptides are identical, and we identify previously unknown congeners. We show that stendomycin can be chemically modified at its electrophilic dehydrobutyrine moiety yielding the first bioactive analogue of this natural product which can undergo additional functionalization. This compound may be a valuable starting point for molecular probe development, and we invite its distribution to the scientific community.
2. Stendomycin selectively inhibits TIM23-dependent mitochondrial protein import
Ireos Filipuzzi, Janos Steffen, Mitchel Germain, Laetitia Goepfert, Michael A Conti, Christoph Potting, Raffaele Cerino, Martin Pfeifer, Philipp Krastel, Dominic Hoepfner, Julie Bastien, Carla M Koehler, Stephen B Helliwell Nat Chem Biol. 2017 Dec;13(12):1239-1244. doi: 10.1038/nchembio.2493. Epub 2017 Oct 9.
Tim17 and Tim23 are the main subunits of the TIM23 complex, one of the two major essential mitochondrial inner-membrane protein translocon machineries (TIMs). No chemical probes that specifically inhibit TIM23-dependent protein import were known to exist. Here we show that the natural product stendomycin, produced by Streptomyces hygroscopicus, is a potent and specific inhibitor of the TIM23 complex in yeast and mammalian cells. Furthermore, stendomycin-mediated blockage of the TIM23 complex does not alter normal processing of the major regulatory mitophagy kinase PINK1, but TIM23 is required to stabilize PINK1 on the outside of mitochondria to initiate mitophagy upon membrane depolarization.
3. Structure activity relationships of stendomycin, a lipopeptide antibiotic from Streptomyces
B Losilla, M T Pommier, N Bonnaveiro, A Cremieux, G Michel Microbios. 1992;71(286):75-80.
A strain of Streptomyces which produced stendomycin, a lipopeptide antibiotic, was grown in culture media containing various amino acids as nitrogen substrates. The nature of the fatty acid component of stendomycin was dependent on the nature of the amino acid present in the medium, but this did not affect antibiotic activity. Modifications in the peptide moiety resulted in a loss of antifungal activity.
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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 ╳
