Sch-38516
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03413 |
| CAS | 128563-23-5 |
| Molecular Weight | 442.6 |
| Molecular Formula | C24H46N2O5 |
Online Inquiry
Description
Sch-38516 is a macrolactam antibiotic produced by Actinomadura sp. SCC 1776 and SCC 1777. It exhibits activity against Candida sp. with MIC of 0.91 µg/mL.
Specification
| Synonyms | Sch 38516 |
| IUPAC Name | (3R,7S,10R,11R)-10-[(2R,3R,4R,5S,6S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-3,11-diethyl-7-methyl-azacyclotetradecan-2-one |
| Canonical SMILES | CCC1CCCNC(=O)C(CCCC(CCC1OC2C(C(C(C(O2)C)O)N)O)C)CC |
| InChI | InChI=1S/C24H46N2O5/c1-5-17-11-8-14-26-23(29)18(6-2)10-7-9-15(3)12-13-19(17)31-24-22(28)20(25)21(27)16(4)30-24/h15-22,24,27-28H,5-14,25H2,1-4H3,(H,26,29)/t15-,16-,17+,18+,19+,20+,21+,22+,24-/m0/s1 |
| InChI Key | MJDWUOZLTDXLJL-PEFIXUBVSA-N |
Properties
| Melting Point | 156-160°C |
Reference Reading
1. Anthelmintic macrolactams from Nonomuraea turkmeniaca MA7381
Sloan Ayers, Deborah L Zink, Joanne Staats Powell, Christine M Brown, Alan Grund, Olga Genilloud, Oscar Salazar, Donald Thompson, Sheo B Singh J Antibiot (Tokyo). 2008 Feb;61(2):59-62. doi: 10.1038/ja.2008.110.
A new macrolactam, fluvirucin B0 (1), and two known macrolactams, Sch 38516/fluvirucin B1 (2) and Sch 39185/fluvirucin B3 (3), have been isolated from an acetone extract of a strain of Nonomuraea turkmeniaca. These compounds were isolated by bioassay-guided fractionation as part of our search for new anthelmintics. The structures of these compounds were elucidated by comparison of their NMR and MS data to those of previously reported fluvirucins, and confirmed by 2D-NMR. 1approximately 3 exhibited in vitro activity (EC90 <1.0 approximately 1.7 microg/ml) against Haemonchus contortus larvae, but were ineffective in reducing worm counts in vivo against Heligmosomoides polygyrus in mice at 50 mg/kg dosed intramuscularly.
2. High-Yielding Enantioselective Synthesis of the Macrolactam Aglycon of Sch 38516 from Two Units of (2R)-2-Ethyl-4-penten-1-ol
M Martín, G Mas, F Urpí, J Vilarrasa Angew Chem Int Ed Engl. 1999 Oct 18;38(20):3086-3089.
The same precursor-namely, (2R)-2-ethyl-4-penten-1-ol-was used to obtain fragments C9-C13 and C1-C8 of 1, the aglycon of Sch 38516 (which is active against Candida sp.) and fluvirucin B(1) (which is active against influenza A virus). The key steps of the synthesis were the aldol-like reaction between the two fragments and the macrolactamization of a 13-azidotridecanoic acid derivative (see scheme). MOM=methoxymethyl, Py=2-pyridyl.
3. Macrolactams: a novel class of antifungal antibiotics produced by Actinomadura spp. SCC 1776 and SCC 1777
V Hegde, M Patel, A Horan, V Gullo, J Marquez, I Gunnarsson, F Gentile, D Loebenberg, A King, M Puar, et al. J Antibiot (Tokyo). 1992 May;45(5):624-32. doi: 10.7164/antibiotics.45.624.
Three novel antifungal antibiotics, Sch 38518, Sch 39185 and Sch 38516 were isolated from the fermentation broths of two actinomycetes identified by chemical, morphological and physiological analysis as a new species of Actinomadura. The compounds were isolated from broth by solvent extraction and purified by silica gel chromatography. Physico-chemical properties, mass spectral analysis, IR and UV suggested the compounds were similar. Sch 38518 and Sch 39185 have a molecular formula of C25H48N2O5. 1H NMR, 13C NMR and hydrolysis indicated the aglycones were identical, however the compounds differed in containing isomeric sugar moieties. Sch 38518 contains mycosamine while Sch 39185 contains 3,6-dideoxy-3-amino-L-talopyranose. Sch 38516 has a molecular formula of C24H46N2O5 and is a lower homolog of Sch 39185. The three compounds, Sch 38518 (1), Sch 39185 (2), and Sch 38516 (3) exhibit similar activity against Candida spp. with geometric mean MICs of 1.81, 2.00 and 0.91 micrograms/ml, respectively.
Recommended Products
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-03753 | Baicalin | 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 ╳
