Amythiamicin C
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| Category | Antibiotics |
| Catalog number | BBF-00462 |
| CAS | 156620-47-2 |
| Molecular Weight | 1183.41 |
| Molecular Formula | C50H50N14O9S6 |
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Description
It is produced by the strain of Amycolatopsis sp. M481-42F4. It has activity against gram-positive bacteria including Multidrug resistant Staphylococcus aureus and Methicillin-resistant Staphylococcus aureus (MR-SA)(MIC 0.1-0.78μg/mL). Not resistant to gram-negative bacteria and fungi.
Specification
| Synonyms | 4-Thiazolecarboxylic acid,2-(10,11,17,18,23,24,25,26,27,28-decahydro-14-methyl-11-(2-methylamino)-2-oxoethyl)-18,28-bis(1-methylethyl)-9,16,23,26-tetraoxo-9H,16H-8,5:15,12:22,19:32,29:36,33-pentanitrilo-5H,29H,33H-pyrido(3,2-a1)(1,11,18,25,31,4,7,14,21)pentathiatetraazacyclotetratriacontin-2-yl)-,(octahydro-1,4-dioxopyrrolo(1,2-a)pyrazin-3-yl)methyl ester |
| IUPAC Name | (1,4-dioxo-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-3-yl)methyl 2-[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-thiazole-4-carboxylate |
| 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)C(=O)OCC8C(=O)N9CCCC9C(=O)N8)C3=NC(=CS3)C(=O)NC(C(=N2)S1)CC(=O)NC)C(C)C)C(C)C |
| InChI | InChI=1S/C50H50N14O9S6/c1-20(2)35-47-59-30(18-78-47)45-56-27(15-75-45)38-23(9-10-24(53-38)44-60-31(19-76-44)50(72)73-14-26-49(71)64-11-7-8-32(64)41(69)55-26)43-57-29(17-74-43)40(68)54-25(12-33(65)51-6)46-63-37(22(5)79-46)42(70)62-36(21(3)4)48-58-28(16-77-48)39(67)52-13-34(66)61-35/h9-10,15-21,25-26,32,35-36H,7-8,11-14H2,1-6H3,(H,51,65)(H,52,67)(H,54,68)(H,55,69)(H,61,66)(H,62,70) |
| InChI Key | RVTQSVRTXQTCKX-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Density | 1.590 g/cm3 |
| Solubility | Soluble in Methanol |
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. Total syntheses of the thiopeptides amythiamicin C and D
Carolin Ammer, Thorsten Bach Chemistry. 2010 Dec 17;16(47):14083-93. doi: 10.1002/chem.201002144.
The thiopeptides amythiamicin C and D were synthesized by employing amide bond formation, a Stille cross-coupling reaction, and two Negishi cross-coupling reactions as key transformations. The central 2,3,6-trisubstituted pyridine ring of the target compounds was introduced as a 2,6-dibromo-3-iodopyridine, which was selectively metalated at the 3-position and connected to the complete Southern fragment of the amythiamicins by a Negishi cross-coupling. For the synthesis of amythiamicin C, this step was followed by a Negishi cross-coupling at C-6 of the pyridine core. Subsequent attachment of the Eastern fragment was achieved by amide bond formation and macrolactam ring closure by a Stille cross-coupling at C-2. The Eastern bithiazole fragment of the amythiamins was constructed also by regioselective metalation and cross-coupling reactions. The pivotal step involved the diastereoselective addition of 4-bromothiazole-2-magnesium bromide to a chiral sulfinyl imine. For the synthesis of amythiamicin D, the order of cross-coupling at C-6, amide bond formation, and cross-coupling at C-2 was changed. The amide bond formation to the Eastern fragment was performed first and it was subsequently attempted to close the macrolactam by an intramolecular regioselective Stille cross-coupling at C-2. Despite the low regioselectivity of this reaction it paved the way to the immediate completion of the amythiamicin D synthesis when followed by a Negishi cross-coupling at C-6 with 2-zincated methyl thiazole-5-carboxylate.
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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 ╳
