Tetrocarcin F1
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| Category | Others |
| Catalog number | BBF-03115 |
| CAS | 81319-50-8 |
| Molecular Weight | 782.87 |
| Molecular Formula | C41H54N2O13 |
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Description
Tetrocarcin F1 is a small component produced by Micromonospora chalcea KY 11091. It has gram-positive bacterial activity, moderate activity against Bacillus subtilis, and weaker activity against Staphylococcus.
Specification
| Synonyms | Antibiotic F1; Tetrocarcin F-1 |
| IUPAC Name | methyl N-[(2R,3R,4S,6R)-6-[[(5S,6R,7E,9S,11Z,13S,16S,17S,18S,20S,21R,22S,23E)-3-formyl-5,17,23-trihydroxy-8,12,18,20,22-pentamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-3,7,11,14,23-pentaen-9-yl]oxy]-2,4-dimethyl-4-nitrooxan-3-yl]carbamate |
| Canonical SMILES | CC1CC(C(C2C1C3(C(C=C2)C(=CCC(C(=CC4C(C=C(CC45C(=O)C(=C3O)C(=O)O5)C=O)O)C)OC6CC(C(C(O6)C)NC(=O)OC)(C)[N+](=O)[O-])C)C)O)C |
| InChI | InChI=1S/C41H54N2O13/c1-19-9-12-29(55-30-17-39(6,43(51)52)34(23(5)54-30)42-38(50)53-8)20(2)14-27-28(45)15-24(18-44)16-41(27)36(48)31(37(49)56-41)35(47)40(7)26(19)11-10-25-32(40)21(3)13-22(4)33(25)46/h9-11,14-15,18,21-23,25-30,32-34,45-47H,12-13,16-17H2,1-8H3,(H,42,50)/b19-9-,20-14+,35-31+/t21-,22-,23+,25-,26-,27+,28-,29-,30-,32+,33-,34-,39-,40+,41?/m0/s1 |
| InChI Key | VDDFIJNQPDATJC-ZJVNHDRWSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 918.2±65.0°C at 760 mmHg |
| Melting Point | 207-210°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Tetrocarcins E1, E2, F and F-1, new antibiotics. Fermentation, isolation and characterization
T Tamaoki, M Kasai, K Shirahata, F Tomita J Antibiot (Tokyo). 1982 Aug;35(8):979-84. doi: 10.7164/antibiotics.35.979.
New components of tetrocarcins (E1, E2, F and F-1) were found in the culture broth of Micromonospora chalcea KY 11091 that was known to produce tetrocarcins A, B and C. Tetrocarcin F-1 consisted of tetronolide and nitro sugar (tetronitrose). Tetrocarcins E1 and E2 consisted of F-1 and deoxy sugar (L-digitoxose). Tetrocarcin F consisted of F-1 and two deoxy sugars (their structures were not yet determined). They all showed antibacterial activities against Gram-positive bacteria and the specific activity decreased with decrease in the numbers of deoxy sugars attached to the aglycone.
2. Tetrocarcin Q, a New Spirotetronate with a Unique Glycosyl Group from a Marine-Derived Actinomycete Micromonospora carbonacea LS276
Ting Gong, Xin Zhen, Xing-Lun Li, Jing-Jing Chen, Tian-Jiao Chen, Jin-Ling Yang, Ping Zhu Mar Drugs. 2018 Feb 24;16(2):74. doi: 10.3390/md16020074.
A new spirotetronate glycoside tetrocarcin Q (1) and six known analogues tetrocarcin A (2), AC6H (3), tetrocarcin N (4), tetrocarcin H (5), arisostatin A (6), and tetrocarcin F1 (7) were isolated from the fermentation broth of the marine-derived actinomycete Micromonospora carbonacea LS276. Their chemical structures were established on the basis of 1D- and 2D-NMR spectroscopy, as well as HR-ESI-MS analysis. The absolute configurations of their stereogenic carbons were determined by circular dichroism (CD) analysis. Compound 1 possesses 2-deoxy-allose, which is a unique sugar type at the C-9 position. This type has not been found in the previously reported spirotetronate glycosides. Compound 1 displayed moderate antibacterial activity against Bacillus subitlis ATCC 63501 with minimum inhibitory concentration (MIC) value of 12.5 μM.
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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 ╳
