Tetrazomine
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| Category | Mycotoxins |
| Catalog number | BBF-03111 |
| CAS | 132073-72-4 |
| Molecular Weight | 458.55 |
| Molecular Formula | C24H34N4O5 |
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Description
Tetrazomine is an antibiotic produced by Saccharothrix mulabilis subsp. chichijimaensis. It is active against gram-positive bacteria, gram-negative bacteria and mycobacteria. It has cytotoxic activity and inhibits lymphoid leukemia L1210 and leukemia P388 with IC50 of 0.047 and 0.0140 μg/mL, respectively.
Specification
| IUPAC Name | (3R)-3-hydroxy-N-[(1S,2S,3R,5R,6R,9R)-3-(hydroxymethyl)-11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.12,5.06,17.010,15]octadeca-10(15),11,13-trien-12-yl]piperidine-2-carboxamide |
| Canonical SMILES | CN1C2CC(C1C3CC4=C(C5N3C2OC5)C(=C(C=C4)NC(=O)C6C(CCCN6)O)OC)CO |
| InChI | InChI=1S/C24H34N4O5/c1-27-16-9-13(10-29)21(27)15-8-12-5-6-14(26-23(31)20-18(30)4-3-7-25-20)22(32-2)19(12)17-11-33-24(16)28(15)17/h5-6,13,15-18,20-21,24-25,29-30H,3-4,7-11H2,1-2H3,(H,26,31)/t13-,15-,16+,17-,18+,20?,21-,24+/m0/s1 |
| InChI Key | WXZSUBHBYQYTNM-WMDJANBXSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria |
| Boiling Point | 664.9±55.0°C at 760 mmHg |
| Melting Point | 190°C(dec.) |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Enantioselective synthesis of the AB-ring system of the antitumor antibiotic tetrazomine
P Wipf, C R Hopkins J Org Chem. 2001 May 4;66(9):3133-9. doi: 10.1021/jo015512q.
The synthesis of the 1,2,3,4-tetrahydroisoquinoline moiety of tetrazomine was accomplished in 18 steps and in 3% overall yield from commercially available o-anisaldehyde. The reaction sequence utilizes a Sharpless asymmetric dihydroxylation to install the stereocenter and an intramolecular Friedel--Crafts hydroxyalkylation with an N-protected 2-oxo-acetamide to close the heterocyclic ring.
2. Total Synthesis of (-)-Tetrazomine and Determination of Its Stereochemistry
Jack D Scott, Robert M Williams Angew Chem Int Ed Engl. 2001 Apr 17;40(8):1463-1465. doi: 10.1002/1521-3773(20010417)40:83.0.CO;2-8.
A new method for the formation of the allylic amine precursor to an azomethine ylide 1 has been developed and exploited in an efficient 1,3-dipolar cycloaddition to afford the key tetracyclic intermediate used in the synthesis of (-)-tetrazomine (2). Bn=benzyl.
3. Total synthesis of (-)-tetrazomine. Determination of the stereochemistry of tetrazomine and the synthesis and biological activity of tetrazomine analogues
Jack D Scott, Robert M Williams J Am Chem Soc. 2002 Mar 27;124(12):2951-6. doi: 10.1021/ja0174027.
The first total synthesis of the potent antitumor antibiotic (-)-tetrazomine has been accomplished. A new method for the formation of the allylic amine precursor to an azomethine ylide has been developed and exploited in an efficient [1,3]-dipolar cycloaddition to afford the key tetracyclic intermediate used in the synthesis of (-)-tetrazomine. Several analogues of tetrazomine have been synthesized and tested for antimicrobial and biochemical activity.
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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 ╳
