Streptovaricin J
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| Category | Antibiotics |
| Catalog number | BBF-03073 |
| CAS | 52275-61-3 |
| Molecular Weight | 811.87 |
| Molecular Formula | C42H53NO15 |
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Description
Streptovaricin J is a macrolide Ansa antibiotic produced by Str. spectabilis NRRL 2494. It has anti-gram-positive bacteria and mycobacterial activity.
Specification
| IUPAC Name | methyl (7E,9Z,11R,12R,13S,14R,15S,16R,17S,18R,19R,20E)-2,12-diacetyloxy-14,16,18,19,31-pentahydroxy-3,7,11,13,17,19,21,27-octamethyl-6,28-dioxo-23,25-dioxa-5-azatetracyclo[20.7.1.14,29.026,30]hentriaconta-1,3,7,9,20,22(30),26,29(31)-octaene-15-carboxylate |
| Canonical SMILES | CC1C=CC=C(C(=O)NC2=C(C(=C3C(=C2O)C(=O)C(=C4C3=C(C(=CC(C(C(C(C(C(C(C1OC(=O)C)C)O)C(=O)OC)O)C)O)(C)O)C)OCO4)C)OC(=O)C)C)C |
| InChI | InChI=1S/C42H53NO15/c1-17-13-12-14-18(2)40(51)43-30-20(4)38(58-25(9)45)26-27(34(30)49)31(46)22(6)37-28(26)36(55-16-56-37)19(3)15-42(10,53)39(50)23(7)33(48)29(41(52)54-11)32(47)21(5)35(17)57-24(8)44/h12-15,17,21,23,29,32-33,35,39,47-50,53H,16H2,1-11H3,(H,43,51)/b13-12-,18-14+,19-15+/t17-,21+,23+,29-,32-,33-,35-,39-,42-/m1/s1 |
| InChI Key | HWZKXYATXCLZAG-SEWHNPOJSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 936.9±65.0°C at 760 mmHg |
| Melting Point | 177-180°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Production of 3-desmethyl protostreptovaricin I from the genetically engineered Streptomyces spectabilis CCTCC M2017417
Yuanzhen Liu, Xiqing Cui, Zhengyuan Li, Xu Chen, Guoping Zeng, Yuhui Sun J Asian Nat Prod Res. 2021 Oct;23(10):1015-1021. doi: 10.1080/10286020.2020.1816976. Epub 2020 Sep 18.
A new streptovaricin analogue, namely 3-desmethyl protostreptovaricin I (1), was isolated from the culture of the genetically engineered strain ΔstvM2 derived from Streptomyces spectabilis CCTCC M2017417. Its structure was elucidated on the basis of extensive spectroscopic analyses, including 1D and 2D NMR tests, and high resolution mass spectrometry analysis. Compound 1 is the first example of 3-desmethyl streptovaricin analogues reported so far, however, it showed no antibacterial activities against Staphylococcus aureus ATCC 29213.
2. Biosynthesis of the streptovaricins: 3-amino-5-hydroxybenzoic acid as a precursor to the meta-C7N unit
A L Staley, K L Rinehart J Antibiot (Tokyo). 1991 Feb;44(2):218-24. doi: 10.7164/antibiotics.44.218.
[Carboxy-14C]-3-amino-5-hydroxybenzoic acid (AHBA) has been shown to be incorporated by Streptomyces spectabilis to the extent of greater than 0.1% (35: 1 dilution) in the ansamycin antibiotic streptovaricin C, the major component of the streptovaricin complex. When [carboxy-13C]AHBA was similarly administered, C-21 (quinone methide carbonyl at 188.3 ppm) of streptovaricin C was specifically labeled (at twenty one times natural abundance). In preparation for the 13C incorporation study the 13C NMR spectrum of streptovaricin C was investigated, making extensive use of short- and long-range HETCOR. These assignments revise some of those proposed earlier for streptovaricin C.
3. Ansavaricin J, a New Heterocyclic Ring-Fused Streptovaricin from Gene stvP5-Deleted Mutant of Streptomyces spectabilis CCTCC M2017417
Yuan-Zhen Liu, Xu Chen, Zheng-Yuan Li, Li-Xia Huang, Yu-Hui Sun Chem Biodivers. 2020 Aug;17(8):e1900713. doi: 10.1002/cbdv.201900713. Epub 2020 Jul 27.
A new ring-fused streptovaricin analogue, named ansavaricin J, was unprecedently isolated from the culture of the genetically modified strains ΔstvP5 which derived from Streptomyces spectabilis CCTCC M2017417. Its structure was elucidated via comprehensive spectroscopic analyses, including 1D- and 2D-NMR tests, and HR-ESI-MS data analysis. Notably, ansavaricin J and E represent the only two reported examples of heterocyclic ring-fused streptovaricins thus far, however, it only showed insignificant antibacterial activities against Staphylococcus aureus.
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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 ╳
