Sch 47555
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| Category | Antibiotics |
| Catalog number | BBF-02427 |
| CAS | 150050-21-8 |
| Molecular Weight | 694.7 |
| Molecular Formula | C37H42O13 |
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Description
Sch 47555 is an antifungal antibiotic produced from Streptomyces sp. SCC-2135.
Specification
| Synonyms | Antibiotic Sch 47555; Sch-47555 |
| IUPAC Name | (3R,4aR,12bS)-4a,8,12b-trihydroxy-9-[5-(5-hydroxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl]-3-methyl-3-[(6-methyl-5-oxo-2H-pyran-2-yl)oxy]-2,4-dihydrobenzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1C(CCC(O1)OC2CCC(OC2C)C3=C(C4=C(C=C3)C(=O)C5=C(C4=O)C=CC6(C5(C(=O)CC(C6)(C)OC7C=CC(=O)C(O7)C)O)O)O)O |
| InChI | InChI=1S/C37H42O13/c1-17-23(38)7-11-28(47-17)49-25-9-10-26(46-19(25)3)20-5-6-21-30(32(20)41)33(42)22-13-14-36(44)16-35(4,50-29-12-8-24(39)18(2)48-29)15-27(40)37(36,45)31(22)34(21)43/h5-6,8,12-14,17-19,23,25-26,28-29,38,41,44-45H,7,9-11,15-16H2,1-4H3/t17?,18?,19?,23?,25?,26?,28?,29?,35-,36-,37-/m0/s1 |
| InChI Key | MCDSLJCOWVFKEL-YBKKMURLSA-N |
Properties
| Appearance | Orange-red Powder |
| Antibiotic Activity Spectrum | fungi; yeast |
| Melting Point | 151-153°C (dec.) |
Reference Reading
1. Angucyclines Sch 47554 and Sch 47555 from Streptomyces sp. SCC-2136: cloning, sequencing, and characterization
Devi Bahdur Basnet, Tae-Jin Oh, Thi Thu Hang Vu, Basundhara Sthapit, Kwangkyoung Liou, Hei Chan Lee, Jin-Cheol Yoo, Jae Kyung Sohng Mol Cells. 2006 Oct 31;22(2):154-62.
The entire gene cluster involved in the biosynthesis of angucyclines Sch 47554 and Sch 47555 was cloned, sequenced, and characterized. Analysis of the nucleotide sequence of genomic DNA spanning 77.5-kb revealed a total of 55 open reading frames, and the deduced products exhibited strong sequence similarities to type II polyketide synthases, deoxysugar biosynthetic enzymes, and a variety of accessory enzymes. The involvement of this gene cluster in the pathway of Sch 47554 and Sch 47555 was confirmed by genetic inactivation of the aromatase, including a portion of the ketoreductase, which was disrupted by inserting the thiostrepton gene.
2. Cloning and expression of glucose-1-phosphate thymidylyltransferase gene (schS6) from Streptomyces sp. SCC-2136
Ji-Man Han, Su-Min Kim, Hyo-Jung Lee, Jin-Cheol Yoo J Microbiol Biotechnol. 2007 Apr;17(4):685-90.
The deoxysugar biosynthetic gene cluster of Sch 47554/Sch 47555 was cloned from Streptomyces sp. SCC-2136. One of the ORFs, schS6, appeared to encode glucose-1-phosphate thymidylyltransferase, which converts dTTP and glucose-1-phosphate to TDP-D-glucose and pyrophosphate. The dTDP-D-glucose is a key metabolite in prokaryotics as a precursor for a large number of modified deoxysugars, and these deoxysugars are a major part of various antibiotics, ranging from glycosides to macrolides. SchS6 was expressed in E. coli vector pSCHS6 and the expressed protein was purified to apparent homogeneity by ammonium sulfate precipitation and Ni-NTA affinity column chromatography. The specific activity of the purified enzyme increased 4.7-fold with 17.5% recovery. It migrated as a single band on SDS-PAGE with an apparent molecular mass of 56 kDa. The purified protein showed glucose-1-phosphate thymidylyltransferase activity, catalyzing a reversible bimolecular group transfer reaction. In the forward reaction, the highest activity was obtained with combination of dTTP and alpha-D-glucose-1-phosphate, and only 12% of that activity was obtained with the substrates UTP/alpha-D-glucose-1-phosphate. In the opposite direction, the purified protein was highly specific for dTDP-D-glucose and pyrophosphate.
3. New Insights into the Glycosylation Steps in the Biosynthesis of Sch47554 and Sch47555
Ozkan Fidan, Riming Yan, Gabrielle Gladstone, Tong Zhou, Du Zhu, Jixun Zhan Chembiochem. 2018 Jul 4;19(13):1424-1432. doi: 10.1002/cbic.201800105. Epub 2018 May 25.
Sch47554 and Sch47555 are antifungal compounds from Streptomyces sp. SCC-2136. The availability of the biosynthetic gene cluster made it possible to track genes that encode biosynthetic enzymes responsible for the structural features of these two angucyclines. Sugar moieties play important roles in the biological activities of many natural products. An investigation into glycosyltransferases (GTs) might potentially help to diversify pharmaceutically significant drugs through combinatorial biosynthesis. Sequence analysis indicates that SchS7 is a putative C-GT, whereas SchS9 and SchS10 are proposed to be O-GTs. In this study, the roles of these three GTs in the biosynthesis of Sch47554 and Sch47555 are characterized. Coexpression of the aglycone and sugar biosynthetic genes with schS7 in Streptomyces lividans K4 resulted in the production of C-glycosylated rabelomycin, which revealed that SchS7 attached a d-amicetose moiety to the aglycone core structure at the C-9 position. Gene inactivation studies revealed that subsequent glycosylation steps took place in a sequential manner, in which SchS9 first attached either an l-aculose or l-amicetose moiety to 4'-OH of the C-glycosylated aglycone, then SchS10 transferred an l-aculose moiety to 3-OH of the angucycline core.
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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 ╳
