Sch-38518
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| Category | Antibiotics |
| Catalog number | BBF-03414 |
| CAS | 135559-94-3 |
| Molecular Weight | 456.7 |
| Molecular Formula | C25H48N2O5 |
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Description
Sch-38518 is a macrolactam antibiotic produced by Actinomadura sp. SCC 1776 and SCC 1777. It exhibits activity against Candida sp. with MIC of 1.81 µg/mL.
Specification
| Synonyms | Sch 38518 |
| IUPAC Name | 10-(4-amino-3,5-dihydroxy-6-methyloxan-2-yl)oxy-3,7,11-triethyl-azacyclotetradecan-2-one |
| Canonical SMILES | CCC1CCCC(C(=O)NCCCC(C(CC1)OC2C(C(C(C(O2)C)O)N)O)CC)CC |
| InChI | InChI=1S/C25H48N2O5/c1-5-17-10-8-11-19(7-3)24(30)27-15-9-12-18(6-2)20(14-13-17)32-25-23(29)21(26)22(28)16(4)31-25/h16-23,25,28-29H,5-15,26H2,1-4H3,(H,27,30) |
| InChI Key | RSMFLBIGOXZFRL-UHFFFAOYSA-N |
Properties
| Melting Point | 220°C |
Reference Reading
1. Identification of the Fluvirucin B2 (Sch 38518) Biosynthetic Gene Cluster from Actinomadura fulva subsp. indica ATCC 53714: substrate Specificity of the β-Amino Acid Selective Adenylating Enzyme FlvN
Akimasa Miyanaga, Yuki Hayakawa, Mario Numakura, Junko Hashimoto, Kuniko Teruya, Takashi Hirano, Kazuo Shin-Ya, Fumitaka Kudo, Tadashi Eguchi Biosci Biotechnol Biochem. 2016 May;80(5):935-41. doi: 10.1080/09168451.2015.1132155. Epub 2016 Jan 28.
Fluvirucins are 14-membered macrolactam polyketides that show antifungal and antivirus activities. Fluvirucins have the β-alanine starter unit at their polyketide skeletons. To understand the construction mechanism of the β-alanine moiety in fluvirucin biosyntheses, we have identified the biosynthetic cluster of fluvirucin B2 produced from Actinomadura fulva subsp. indica ATCC 53714. The identified gene cluster contains three polyketide synthases, four characteristic β-amino acid-carrying enzymes, one decarboxylase, and one amidohydrolase. We next investigated the activity of the adenylation enzyme FlvN, which is a key enzyme for the selective incorporation of a β-amino acid substrate. FlvN showed strong preference for l-aspartate over other amino acids such as β-alanine. Based on these results, we propose a biosynthetic pathway for fluvirucin B2.
2. Efficient approach to fluvirucins B2-B5, Sch 38518, and Sch 39185. First synthesis of their aglycon, via CM and RCM reactions
Enric Llàcer, Fèlix Urpí, Jaume Vilarrasa Org Lett. 2009 Aug 6;11(15):3198-201. doi: 10.1021/ol901030f.
A route to fluvirucinins B(2-5) (the common aglycon of fluvirucins B(2)-B(5), Sch 38518, and Sch 39185) is reported for the first time. A ring-closing metathesis (RCM) generated the C6-C7 double bond, which by catalytic hydrogenation (in toluene) gave the desired epimer with a 9:1 diastereoselection. Azide 8a and carboxylic acid 5 came from ethyl-branched fragments C9-C13 (CHO at C9) and C1-C5 via an asymmetric allylation of the former and a cross metathesis (CM) followed by a ketone methylenation (with 20 mol % of DMF as a sacrificial additive) of the latter.
3. A novel macrolactam-trisaccharide antifungal antibiotic. Taxonomy, fermentation, isolation, physico-chemical properties, structure elucidation and biological activity
V R Hegde, M G Patel, A C Horan, A H King, F Gentile, M S Puar, D Loebenberg J Antibiot (Tokyo). 1998 May;51(5):464-70. doi: 10.7164/antibiotics.51.464.
A novel secondary metabolite SCH 42282 (1), with antifungal activity was isolated from the fermentation broth of a soil actinomycete identified as a Microtetraspora sp. The active compound was separated from the fermentation broth by butanol extraction and purified on a silica gel column and by multi-coil counter current chromatography. The compound was identified as a novel macrolactam trisaccharide related to SCH 38518 (4). The structure was established by hydrolysis of the parent compound and spectroscopic studies of the acetate derivative. The compound is active against Candida spp. (Geometric Mean MIC's. 18 micrograms/ml) but less active SCH 42729 (3). the disaccharide (Geometric Mean MIC's, > or = 10.7 micrograms/ml and SCH 38518 (4), the monosaccharide (Geometric Mean Mic's, 3.8 micrograms/ml.
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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 ╳
