Fluvirucin A1
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| Category | Antibiotics |
| Catalog number | BBF-01425 |
| CAS | 137019-37-5 |
| Molecular Weight | 428.60 |
| Molecular Formula | C23H44N2O5 |
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Description
Fluvirucin A1 is produced by Actinomycete Q464-31. It has the activity against influenza virus.
Specification
| Synonyms | 3-((3-Amino-3,6-dideoxy-alpha-L-talopyranosyl)oxy)-2,6-dimethyl-10-ethyl-13-tridecanelactam |
| IUPAC Name | (3R,4S,7R,11S)-4-[(2R,3R,4R,5S,6S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-11-ethyl-3,7-dimethyl-azacyclotetradecan-2-one |
| Canonical SMILES | CCC1CCCC(CCC(C(C(=O)NCCC1)C)OC2C(C(C(C(O2)C)O)N)O)C |
| InChI | InChI=1S/C23H44N2O5/c1-5-17-9-6-8-14(2)11-12-18(15(3)22(28)25-13-7-10-17)30-23-21(27)19(24)20(26)16(4)29-23/h14-21,23,26-27H,5-13,24H2,1-4H3,(H,25,28)/t14-,15-,16+,17+,18+,19-,20-,21-,23+/m1/s1 |
| InChI Key | ZRJBXPCQRSLIKK-BDPAYSQHSA-N |
Properties
| Appearance | Colorless Acicular Crystalline |
| Antibiotic Activity Spectrum | viruses |
| Boiling Point | 624°C at 760 mmHg |
| Melting Point | 275-277°C |
| Density | 1.1 g/cm3 |
Reference Reading
1. Fluvirucins A1, A2, B1, B2, B3, B4 and B5, new antibiotics active against influenza A virus. III. The stereochemistry and absolute configuration of fluvirucin A1
N Naruse, M Konishi, T Oki, Y Inouye, H Kakisawa J Antibiot (Tokyo). 1991 Jul;44(7):756-61. doi: 10.7164/antibiotics.44.756.
Fluvirucin A1 was established as (2R,3S,6R, 10S)-3-[(3-amino-3,6-dideoxy-alpha-L-talopyranosyl)-oxy]-2,6-dimethyl-10 -ethyl-13-tridecanelactam by chemical, spectroscopic, and X-ray crystallographic analyses.
2. Fluvirucins A1, A2, B1, B2, B3, B4 and B5, new antibiotics active against influenza A virus. IV. Taxonomy on the producing organisms
K Tomita, N Oda, Y Hoshino, N Ohkusa, H Chikazawa J Antibiot (Tokyo). 1991 Sep;44(9):940-8. doi: 10.7164/antibiotics.44.940.
The morphology, chemotaxonomy, and cultural and physiological characteristics were examined on the five strains of actinomycetes which produce antiviral antibiotics, fluvirucin congeners. All strains have meso-2,6-diaminopimelic acid in the cell wall. Four strains, Q464-31, L407-5, R359-5 and R516-16, belong to the maduromycetes since they have madurose in the whole cell. The remaining one strain, R869-90, has rhamnose but no madurose, and is a nocardioform actinomycete. These five strains were classified and designated as follows: Strain Q464-31 (fluvirucin A1 producer): Microtetraspora tyrrhenii sp. nov. (Actinomadura pusilla group). Strain L407-5 (fluvirucin B2 producer): A maduromycete. Strain R359-5 (fluvirucin B1 producer): Microtetraspora pusilla (Actinomadura pusilla group). Strain R869-90 (fluvirucin A2 producer): Saccharothrix mutabilis. Strain R516-16 (fluvirucins B2, B3, B4 and B5 producer): A maduromycete.
3. Highly efficient asymmetric synthesis of fluvirucinine A1 via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)-lipase-catalyzed acetylation tandem process
Bo Liang, Ei-ichi Negishi Org Lett. 2008 Jan 17;10(2):193-5. doi: 10.1021/ol702272d. Epub 2007 Dec 13.
ZACA-lipase-catalyzed acetylation tandem process has been shown to proceed satisfactorily with either TBS-protected 4-penten-1-ol or 3-buten-1-ol to provide the corresponding enantiomerically pure (R)-2-ethyl-1-alkanols. Either (R)-5 or (R)-6 was converted to 3 in seven steps. The other fragment 4 was synthesized in nine steps from (-)-(S)-citronellol. Conversion of 3 and 4 into 99% pure fluvirucinine A1 was achieved in four steps via amidation-ring closing metathesis, the overall yield in the longest linear sequence being 34% (13 steps).
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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 ╳
