Sarkomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02885 |
| CAS | 489-21-4 |
| Molecular Weight | 140.14 |
| Molecular Formula | C7H8O3 |
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Description
It is a cyclopentane derivative of antibiotic produced by the strain of Str. erythrochromogenes W-115-C. It has anti-bacterial effect, but the effect is weak. Serum and cysteine can reduce its antibacterial activity. It can inhibit HeLa cells and Eichler ascites cancer cells in vitro.
Specification
| Related CAS | 11031-48-4 874-21-5 (sodium salt) |
| Synonyms | Sarkomycin; (r)-sarkomycin; (R)-2-methylene-3-oxocyclopentanecarboxylic acid; Cyclopentanecarboxylic acid, 2-methylene-3-oxo-, (R)-; Sarcomycin |
| IUPAC Name | (1R)-2-methylidene-3-oxocyclopentane-1-carboxylic acid |
| Canonical SMILES | C=C1C(CCC1=O)C(=O)O |
| InChI | InChI=1S/C7H8O3/c1-4-5(7(9)10)2-3-6(4)8/h5H,1-3H2,(H,9,10)/t5-/m1/s1 |
| InChI Key | ILFPCMXTASDZKM-RXMQYKEDSA-N |
Properties
| Appearance | Colorless Oily Matter |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 320.3°C at 760 mmHg |
| Melting Point | 159°C (dec.) |
| Density | 1.23 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Microbial Baeyer-Villiger reaction of bicyclo[3.2.0]heptan-6-ones--a novel approach to sarkomycin A
K Königsberger, H Griengl Bioorg Med Chem. 1994 Jul;2(7):595-604. doi: 10.1016/0968-0896(94)85006-2.
Racemic (1 alpha, 2 alpha, 5 alpha)- and (1 beta, 2 alpha, 5 beta)-2- bromobicyclo[3.2.0]heptan-6-one (rac-7, rac-10, respectively), (1 alpha, 2 alpha, 5 beta)- and (1 beta, 2 alpha, 5 beta)-2- benzyloxybicyclo[3.2.0]heptan-6-one (rac-15, rac-13, respectively), (1 beta, 2 alpha, 5 beta)-2-hydroxybicyclo[3.2.0]heptan-6-one (rac-17) and cis-bicyclo[3.2.0]hept-2-en-7-one (rac-18) were subjected to a microbial Baeyer-Villiger reaction by Acinetobacter calcoaceticus NCIB 9871. In each case both regioisomeric lactones were formed (67-93% yield) having always the opposite configuration (20 to > 99 % e.e.). Both the ratio of the regioisomers and the enantiomeric excess proved to be dependent on the type of substitution. Analogously cis-bicyclo[3.2.0]heptan-2,6-dione (rac-1) gave besides other products cyclosarkomycin (1b) (7 % yield, 97 % e.e.). Compound 1b was also obtained from the Baeyer-Villiger product of rac-17 by Swern oxidation (total yield starting from rac-17 9 %, > 98 % e.e.).
2. Total synthesis of (R)-sarkomycin via asymmetric rhodium-catalyzed conjugate addition
Johannes Westmeier, Steffen Kress, Christopher Pfaff, Paultheo von Zezschwitz J Org Chem. 2013 Nov 1;78(21):10718-23. doi: 10.1021/jo4016979. Epub 2013 Oct 14.
(R)-Sarkomycin was prepared using a five-step total synthesis. Key steps in the enantioselective construction of the targeted scaffold were a rhodium-catalyzed asymmetric conjugate alkenyl addition with subsequent silyl trapping and a Mukaiyama aldol reaction with aqueous formaldehyde. Protection of the hydroxy group as a THP acetal and oxidative cleavage of the C,C-double bond provided a stable direct precursor to the natural product. The final liberation was carried out under slightly acidic conditions in a microwave-assisted reaction, resulting in a high yield of the "deceptive" sarkomycin. This represents the shortest enantioselective synthesis of this rather unstable compound to date and the first to employ asymmetric catalysis to introduce the stereogenic center.
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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 ╳
