Virginiamycin S2
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| Category | Antibiotics |
| Catalog number | BBF-02966 |
| CAS | 33477-38-2 |
| Molecular Weight | 811.88 |
| Molecular Formula | C42H49N7O10 |
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Description
It is a depsipeptide antibiotic produced by the strain of Str. virginiae and Str. virginiae var. sp. It has anti-gram-positive bacteria and mycobacterium effects, and the antibacterial activity of component M of Virginiamycin against cocci is stronger than component S, while the activity is stronger than component M.
Specification
| Synonyms | Staphylomycin-S2; 4-L-Phenylalanine-5-(cis-4-hydroxy-L-2-piperidinecarboxylic acid)virginiamycin S1; N-[(3-Hydroxy-2-pyridinyl)carbonyl]cyclo[L-Thr*-D-Abu-L-Pro-L-Phe-[(4R)-4-hydroxy-L-pipecoloyl]-L-phenyl-Gly-]; N-[(3-Hydroxy-2-pyridyl)carbonyl]-cyclo[L-Thr*-D-Abu-L-Pro-L-Phe-4β-hydroxy-L-Hpr-L-phenyl-Gly-] |
| IUPAC Name | N-[(3S,6S,12R,15S,16R,19S,22S,24S)-3-benzyl-12-ethyl-24-hydroxy-16-methyl-2,5,11,14,18,21-hexaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide |
| Canonical SMILES | CCC1C(=O)N2CCCC2C(=O)NC(C(=O)N3CCC(CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)O)CC6=CC=CC=C6 |
| InChI | InChI=1S/C42H49N7O10/c1-3-28-40(56)48-20-11-16-30(48)36(52)45-29(22-25-12-6-4-7-13-25)41(57)49-21-18-27(50)23-31(49)37(53)47-34(26-14-8-5-9-15-26)42(58)59-24(2)33(38(54)44-28)46-39(55)35-32(51)17-10-19-43-35/h4-10,12-15,17,19,24,27-31,33-34,50-51H,3,11,16,18,20-23H2,1-2H3,(H,44,54)(H,45,52)(H,46,55)(H,47,53)/t24-,27+,28-,29+,30+,31+,33+,34+/m1/s1 |
| InChI Key | LRSRCZBNIGNEHL-NTXCPLLSSA-N |
Properties
| Appearance | White Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria |
| Solubility | Soluble in Methanol, Ethanol |
Reference Reading
1. Quinupristin (RP 57669): a new tool to investigate ribosome-group B streptogramin interactions
D Beyer, P Vannuffel, K Pepper Biol Chem. 1998 Jul;379(7):841-6. doi: 10.1515/bchm.1998.379.7.841.
Streptogramin antibiotics consist of two types of molecules, group A and group B. The group B molecule quinupristin (RP 57669) and the group A molecule dalfopristin (RP 54476) constitute the first water-soluble semisynthetic streptogramin, quinupristin/dalfopristin (RP 59500). When group B molecules bind to 50S subunits or to tightly coupled ribosomes, there is an increase in their fluorescence intensity, which is proportional to the concentration of the antibiotic-ribosome complex formed. We found here that the background fluorescence of unbound quinupristin is 10-fold lower than that of unbound virginiamycin S, a natural group B molecule often used experimentally. The association constants were found (i) to be similar for the binding of the two group B molecules to tightly coupled 70S ribosomes in the absence of the group A molecules (quinupristin: 3.5 x 10(7) M(-1); virginiamycin S: 2.8 x 10(7) M(-1)) and (ii) to similarly increase about 20-fold in the presence of the corresponding group A molecule (quinupristin + dalfopristin: 69 x 10(7) M(-1); virginiamycin S + virginiamycin M: 60 x 10(7) M(-1)). Similar results were obtained with 50S ribosomal subunits. Additionally, we provide evidence that the failure of the group B molecules to inhibit poly(Phe) synthesis is due to the displacement of the group B molecule during poly(Phe) polymerization on the ribosome, indicating that the artificial poly(Phe) peptide competes with the binding of the group B molecule.
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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 ╳
