Neoantimycin
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| Category | Antibiotics |
| Catalog number | BBF-02596 |
| CAS | 22862-63-1 |
| Molecular Weight | 698.75 |
| Molecular Formula | C36H46N2O12 |
| Purity | >98% by HPLC |
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Description
A rare and unusual ring-extended member of the antimycin class; produced by a streptomyces species unrelated to antimycin-producing strains; a selective GRP78 molecular chaperone down-regulator highlights the potential of this class as research probes.
Specification
| Synonyms | Salicylamide, N-(15-benzyl-10-sec-butyl-14-hydroxy-3-isopropyl-7,13,13-trimethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraoxacyclopentadec-6-yl)-3-formamido- |
| Storage | Store at -20°C |
| IUPAC Name | N-(15-benzyl-10-butan-2-yl-14-hydroxy-7,13,13-trimethyl-2,5,9,12-tetraoxo-3-propan-2-yl-1,4,8,11-tetraoxacyclopentadec-6-yl)-3-formamido-2-hydroxybenzamide |
| Canonical SMILES | CCC(C)C1C(=O)OC(C(C(=O)OC(C(=O)OC(C(C(C(=O)O1)(C)C)O)CC2=CC=CC=C2)C(C)C)NC(=O)C3=C(C(=CC=C3)NC=O)O)C |
| InChI | InChI=1S/C36H46N2O12/c1-8-20(4)29-34(45)47-21(5)26(38-31(42)23-15-12-16-24(27(23)40)37-18-39)32(43)49-28(19(2)3)33(44)48-25(17-22-13-10-9-11-14-22)30(41)36(6,7)35(46)50-29/h9-16,18-21,25-26,28-30,40-41H,8,17H2,1-7H3,(H,37,39)(H,38,42) |
| InChI Key | JIJATTFJYJZEBT-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Acicular Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 930.35°C at 760 mmHg |
| Melting Point | 121-122°C |
| Density | 1.30 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1.Nuclear magnetic resonance and biosynthetic studies of neoantimycin and structure elucidation of isoneoantimycin, a minor metabolite related to neoantimycin.
Takeda Y1, Masuda T, Matsumoto T, Takechi Y, Shingu T, Floss HG. J Nat Prod. 1998 Aug;61(8):978-81.
In preparation for biosynthetic studies on the 3,4-dihydroxy-2, 6-dimethyl-5-phenylvaleric acid portion of neoantimycin (1), the 1H and 13C NMR signals of 1 were assigned unambiguously by means of 2D correlation spectroscopy and NOE experiments. The previously undetermined absolute stereochemistry at C-15 and C-16 was deduced as (S) and (S). The structure of isoneoantimycin (2) was also elucidated. The methyl groups of methionine and propionate were incorporated stereospecifically into C-13 and C-12 of 1, respectively, and the configuration of the methyl group of methionine is inverted in the process. The results also suggest the intervention of phenylpyruvate as an actual precursor.
2.Chemical variation from the neoantimycin depsipeptide assembly line.
Li X1, Zvanych R, Vanner SA, Wang W, Magarvey NA. Bioorg Med Chem Lett. 2013 Sep 15;23(18):5123-7. doi: 10.1016/j.bmcl.2013.07.031. Epub 2013 Jul 24.
Here we report the biosynthetic pathway for the neoantimycin and present three novel neoantimycin analogues, neoantimycin D (1), E (2) and F (3), from this assembly system from Streptoverticillium orinoci. Identification of these novel neoantimycin variants was achieved by selective MS/MS interrogation of natural product extracts using diagnostic fragments of the known neoantimycins. Their structures, including the absolute configurations, were elucidated using a combination of NMR experiments, detailed MS/MS experiments and the advanced Marfey's method. The biosynthetic pathway of neoantimycin was dissected by genome sequencing data analysis for the first time, which includes a hybrid nonribosomal peptide synthetase (NRPS) and polyketide synthetase (PKS) assembly lines.
3.Unantimycin A, a new neoantimycin analog isolated from a microbial metabolite fraction library.
Lim CL1,2, Nogawa T1, Okano A1, Futamura Y1, Kawatani M1, Takahashi S3, Ibrahim D2, Osada H1. J Antibiot (Tokyo). 2015 Dec 9. doi: 10.1038/ja.2015.124. [Epub ahead of print]
4.The structure of neoantimycin.
Caglioti L, Misiti D, Mondelli R, Selva A, Arcamone F, Cassinelli G. Tetrahedron. 1969 May;25(10):2193-221.
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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 ╳
