Amythiamicin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00460 |
| CAS | 152741-89-4 |
| Molecular Weight | 1182.43 |
| Molecular Formula | C50H51N15O8S6 |
| Purity | >98% |
Online Inquiry
Description
Amythiamicin A is a cyclic thiazole peptide produced by Amycolatopsis sp. MI 481-42F4A. It has antibacterial activity against gram-positive bacteria.
Specification
| Synonyms | MI 481-42F4A; Antibiotic MI 481-42F4A; NSC677423; Amythiamycin A |
| Sequence | SCNCVCGVCCSCSP |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-1-[(4S)-2-[2-[(18S,25S,35S)-21-methyl-18-[2-(methylamino)-2-oxoethyl]-16,23,30,33-tetraoxo-25,35-di(propan-2-yl)-3,13,20,27,37-pentathia-7,17,24,31,34,39,40,41,42,43-decazaheptacyclo[34.2.1.12,5.112,15.119,22.126,29.06,11]tritetraconta-1(38),2(43),4,6(11),7,9,12(42),14,19(41),21,26(40),28,36(39)-tridecaen-8-yl]-1,3-thiazol-4-yl]-4,5-dihydro-1,3-oxazole-4-carbonyl]pyrrolidine-2-carboxamide |
| Canonical SMILES | CC1=C2C(=O)NC(C3=NC(=CS3)C(=O)NCC(=O)NC(C4=NC(=CS4)C5=NC(=CS5)C6=C(C=CC(=N6)C7=NC(=CS7)C8=NC(CO8)C(=O)N9CCCC9C(=O)N)C3=NC(=CS3)C(=O)NC(C(=N2)S1)CC(=O)NC)C(C)C)C(C)C |
| InChI | InChI=1S/C50H51N15O8S6/c1-20(2)35-48-61-31(19-78-48)46-57-27(15-75-46)38-23(9-10-24(54-38)45-60-30(18-76-45)43-56-26(14-73-43)50(72)65-11-7-8-32(65)39(51)68)44-58-29(17-74-44)41(70)55-25(12-33(66)52-6)47-64-37(22(5)79-47)42(71)63-36(21(3)4)49-59-28(16-77-49)40(69)53-13-34(67)62-35/h9-10,15-21,25-26,32,35-36H,7-8,11-14H2,1-6H3,(H2,51,68)(H,52,66)(H,53,69)(H,55,70)(H,62,67)(H,63,71)/t25-,26-,32-,35-,36-/m0/s1 |
| InChI Key | BAGBLRBLZUISAJ-DVMLEBHQSA-N |
Properties
| Appearance | Lyophilized Powder or Liquid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Density | 1.7±0.1 g/cm3 |
| Solubility | Soluble in Methanol, DMSO; Poorly soluble in Water, Hexane |
Reference Reading
1. Total syntheses of amythiamicins A, B and C
K C Nicolaou, Dattatraya H Dethe, David Y-K Chen Chem Commun (Camb). 2008 Jun 21;(23):2632-4. doi: 10.1039/b805069b. Epub 2008 May 8.
Total syntheses of the thiopeptide antibiotics amythiamicins A, B and C are reported.
2. Novel antibiotics, amythiamicins. III. Structure elucidations of amythiamicins A, B and C
K Shimanaka, Y Takahashi, H Iinuma, H Naganawa, T Takeuchi J Antibiot (Tokyo). 1994 Oct;47(10):1153-9. doi: 10.7164/antibiotics.47.1153.
The structures of novel antimicrobial antibiotics, amythiamicins A, B and C, were elucidated by chemical degradations and NMR spectral analyses. The main frame from C-1 to C-41 of these antibiotics was the same as that of amythiamicin D. Amino acid autoanalyses of amythiamicins A, B and C showed that these have another one mole of serine and proline in comparison with amythiamicin D. Stereochemistries of both amino acids were determined to be L by chiral HPLC. These seryl-prolyl residues in amythiamicins A, B and C are attached at C-41 through an oxazoline ring, amide and ester bond, respectively.
3. Antibiotic inhibitors of organellar protein synthesis in Plasmodium falciparum
B Clough, K Rangachari, M Strath, P R Preiser, R J Wilson Protist. 1999 Aug;150(2):189-95. doi: 10.1016/s1434-4610(99)70021-0.
Elongation factor Tu (EF-Tu) is encoded by the tuf gene of the plastid organelle of the malaria parasite Plasmodium falciparum. A range of structurally unrelated inhibitors of this GTP-dependent translation factor was shown to have antimalarial activity in blood cultures. The most active was the cyclic thiazolyl peptide amythiamicin A with an IC50 = 0.01 microM. Demonstrable complexes were formed in vitro between a recombinant version of P. falciparum EF-Tu(pl) and inhibitors that bind to different sites on EF-Tu; these included the antibiotics kirromycin, GE2270A and enacyloxin IIa.
Recommended Products
| BBF-03753 | Baicalin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01825 | Loganin | 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 ╳
