Racemomycin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02168 |
| CAS | 3808-42-2 |
| Molecular Weight | 502.52 |
| Molecular Formula | C19H34N8O8 |
| Purity | >98% |
Online Inquiry
Description
It is produced by the strain of Str. racemochromogenes 229. It has broad spectrum antibacterial activity and antifungal effect, and it can inhibit PR-8 of influenza virus in tissue culture.
Specification
| Synonyms | Streptothricin F; Yazumycin A; Streptothricin VI; Antibiotic S 15-1A; BRN 6031385; 2-((O-(Aminocarbonyl)-2-deoxy-2-((3,6-diamino-1-oxohexyl)amino)-beta-D-gulopyranosyl)amino)-1,3,5,6,7,7a-hexahydro-7-hydroxy-4H-imidazo(4,5-c)pyridin-4-one |
| Storage | Store at -20°C |
| IUPAC Name | [(2R,3R,4S,5R,6R)-6-[[(3aS,7R,7aS)-7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl]amino]-5-[[(3S)-3,6-diaminohexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] carbamate |
| Canonical SMILES | C1C(C2C(C(=O)N1)N=C(N2)NC3C(C(C(C(O3)CO)OC(=O)N)O)NC(=O)CC(CCCN)N)O |
| InChI | InChI=1S/C19H34N8O8/c20-3-1-2-7(21)4-10(30)24-13-14(31)15(35-18(22)33)9(6-28)34-17(13)27-19-25-11-8(29)5-23-16(32)12(11)26-19/h7-9,11-15,17,28-29,31H,1-6,20-21H2,(H2,22,33)(H,23,32)(H,24,30)(H2,25,26,27)/t7-,8+,9+,11+,12-,13+,14-,15-,17+/m0/s1 |
| InChI Key | NRAUADCLPJTGSF-VLSXYIQESA-N |
Properties
| Appearance | White Hygroscopic Powder |
| Antibiotic Activity Spectrum | fungi; viruses |
| Boiling Point | 592.64°C at 760 mmHg |
| Melting Point | >210°C |
| Density | 1.3824 g/cm3 |
Reference Reading
1. Biosynthesis of streptolidine involved two unexpected intermediates produced by a dihydroxylase and a cyclase through unusual mechanisms
Chin-Yuan Chang, Syue-Yi Lyu, Yu-Chen Liu, Ning-Shian Hsu, Chih-Chung Wu, Cheng-Fong Tang, Kuan-Hung Lin, Jin-Yuan Ho, Chang-Jer Wu, Ming-Daw Tsai, Tsung-Lin Li Angew Chem Int Ed Engl. 2014 Feb 10;53(7):1943-8. doi: 10.1002/anie.201307989. Epub 2014 Jan 21.
Streptothricin-F (STT-F), one of the early-discovered antibiotics, consists of three components, a β-lysine homopolymer, an aminosugar D-gulosamine, and an unusual bicyclic streptolidine. The biosynthesis of streptolidine is a long-lasting but unresolved puzzle. Herein, a combination of genetic/biochemical/structural approaches was used to unravel this problem. The STT gene cluster was first sequenced from a Streptomyces variant BCRC 12163, wherein two gene products OrfP and OrfR were characterized in vitro to be a dihydroxylase and a cyclase, respectively. Thirteen high-resolution crystal structures for both enzymes in different reaction intermediate states were snapshotted to help elucidate their catalytic mechanisms. OrfP catalyzes an Fe(II) -dependent double hydroxylation reaction converting L-Arg into (3R,4R)-(OH)2 -L-Arg via (3S)-OH-L-Arg, while OrfR catalyzes an unusual PLP-dependent elimination/addition reaction cyclizing (3R,4R)-(OH)2 -L-Arg to the six-membered (4R)-OH-capreomycidine. The biosynthetic mystery finally comes to light as the latter product was incorporation into STT-F by a feeding experiment.
2. The convergent total synthesis and antibacterial profile of the natural product streptothricin F
Matthew G Dowgiallo, Brandon C Miller, Mintesinot Kassu, Kenneth P Smith, Andrew D Fetigan, Jason J Guo, James E Kirby, Roman Manetsch Chem Sci. 2022 Feb 25;13(12):3447-3453. doi: 10.1039/d1sc06445b. eCollection 2022 Mar 24.
A convergent, diversity-enabling total synthesis of the natural product streptothricin F has been achieved. Herein, we describe the potent antimicrobial activity of streptothricin F and highlight the importance of a total synthesis that allows for the installation of practical divergent steps for medicinal chemistry exploits. Key features of our synthesis include a Burgess reagent-mediated 1,2-anti-diamine installation, diastereoselective azidation of a lactam enolate, and a mercury(ii) chloride-mediated desulfurization-guanidination. The development of this chemistry enables the synthesis and structure-activity studies of streptothricin F analogs.
3. Mining of a streptothricin gene cluster from Streptomyces sp. TP-A0356 genome via heterologous expression
Jine Li, Zhengyan Guo, Wei Huang, Xiangxi Meng, Guomin Ai, Gongli Tang, Yihua Chen Sci China Life Sci. 2013 Jul;56(7):619-27. doi: 10.1007/s11427-013-4504-2. Epub 2013 Jul 6.
Streptothricins (STs) are used commercially to treat bacterial and fungal diseases in agriculture. Mining of the sequenced microbial genomes uncovered two cryptic ST clusters from Streptomyces sp. C and Streptomyces sp. TP-A0356. The ST cluster from S. sp. TP-A0356 was verified by successful heterologous expression in Streptomyces coelicolor M145. Two new ST analogs were produced together with streptothricin F and streptothricin D in the heterologous host. The ST cluster was further confirmed by inactivation of gene stnO, which was proposed encoding an aminomutase supplying β-lysines for the poly-β-Lys chain formation. A putative biosynthetic pathway for STs is proposed based on bioinformatics analyses of the ST genes and experimental evidence.
Recommended Products
| BBF-02614 | Nystatin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
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 ╳
