Amythiamicin B
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| Category | Antibiotics |
| Catalog number | BBF-00461 |
| CAS | 156620-48-3 |
| Molecular Weight | 1200.44 |
| Molecular Formula | C50H53N15O9S6 |
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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 | L-Prolinamide, N-((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)-4-thiazolyl)carbonyl)-L-seryl- |
| IUPAC Name | N-[1-(2-carbamoylpyrrolidin-1-yl)-3-hydroxy-1-oxopropan-2-yl]-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-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)C(=O)NC(CO)C(=O)N8CCCC8C(=O)N)C9=NC(=CS9)C(=O)NC(C(=N2)S1)CC(=O)NC)C(C)C)C(C)C |
| InChI | InChI=1S/C50H53N15O9S6/c1-20(2)35-48-61-31(19-79-48)46-57-27(15-76-46)38-23(9-10-24(54-38)45-59-30(18-77-45)42(72)56-26(14-66)50(74)65-11-7-8-32(65)39(51)69)44-58-29(17-75-44)41(71)55-25(12-33(67)52-6)47-64-37(22(5)80-47)43(73)63-36(21(3)4)49-60-28(16-78-49)40(70)53-13-34(68)62-35/h9-10,15-21,25-26,32,35-36,66H,7-8,11-14H2,1-6H3,(H2,51,69)(H,52,67)(H,53,70)(H,55,71)(H,56,72)(H,62,68)(H,63,73) |
| InChI Key | ZVLJONLPGJUTCW-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Density | 1.413 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Novel antibiotics, amythiamicins. I. Taxonomy, fermentation, isolation, physico-chemical properties, and antimicrobial activity
K Shimanaka, N Kinoshita, H Iinuma, M Hamada, T Takeuchi J Antibiot (Tokyo). 1994 Jun;47(6):668-74. doi: 10.7164/antibiotics.47.668.
Novel antibacterial antibiotics, amythiamicins A, B, C and D, have been isolated from the fermentation broth of Amycolatopsis sp. MI481-42F4. In this paper, the taxonomy of the producing strain, fermentation, isolation, physico-chemical properties and biological activities of amythiamicins are reported. Amythiamicins inhibit the growth of Gram-positive bacteria including multi-drug resistant strains.
2. 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.
3. 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.
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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 ╳
