SB-311009
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03403 |
| CAS | |
| Molecular Weight | 408.5 |
| Molecular Formula | C22H36N2O5 |
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Description
SB-311009 is an inhibitor of lipoprotein associated phospholipase A2 produced by Pseudomonas fluorescens DSM 11579.
Specification
| Synonyms | SB 311009; SB311009 |
| IUPAC Name | (3R)-N-[(2Z)-2-[(7aR)-3-oxo-5,6,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl]-3-hydroxytetradecanamide |
| Canonical SMILES | CCCCCCCCCCCC(CC(=O)NC(=O)C=C1C2CCCN2C(=O)O1)O |
| InChI | InChI=1S/C22H36N2O5/c1-2-3-4-5-6-7-8-9-10-12-17(25)15-20(26)23-21(27)16-19-18-13-11-14-24(18)22(28)29-19/h16-18,25H,2-15H2,1H3,(H,23,26,27)/b19-16-/t17-,18-/m1/s1 |
| InChI Key | BKTRZTWFZZFTDL-SRKGJJLTSA-N |
Properties
| Appearance | Colorless Crystal |
Reference Reading
1. Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues
Jeremy R Duvall, Fanghui Wu, Barry B Snider J Org Chem. 2006 Oct 27;71(22):8579-90. doi: 10.1021/jo061650+.
The proposed structures of jenamidines A, B, and C (1-3) were revised to jenamidines A1/A2, B1/B2, and C (8-10). Jenamidines A1/A2 (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA (76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.
2. SB-253514 and analogues: novel inhibitors of lipoprotein associated phospholipase A2 produced by Pseudomonas fluorescens DSM 11579. II. Physico-chemical properties and structure elucidation
D J Busby, R C Copley, J A Hueso, S A Readshaw, A Rivera J Antibiot (Tokyo). 2000 Jul;53(7):670-6.
A series of novel inhibitors of lipoprotein associated phospholipase A2 were isolated from the culture broths of Pseudomonas fluorescens strain DSM11579. The inhibitors fall into two structurally isomeric classes each of which comprise compounds incorporating glycosylated hydrocarbon chains. The structure elucidation for the major member of each structural class is reported. The crystal structure of a non-glycosylated analogue of the 5,5-series, produced through biotransformation, is also reported.
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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 ╳
