Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA017180
PROPERTIES
| NPAID | NPA017180 |
|---|---|
| CLUSTER ID | 112 |
| NODE ID | 106 |
| NAME | Platensimycin |
| FORMULA | C24H27NO7 |
| MOLECULAR WEIGHT (Da) | 441.4800 |
| ACCURATE MASS (Da) | 441.1788 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | platensis MA7327 |
| InChIKey | CSOMAHTTWTVBFL-OFBLZTNGSA-N |
| InChI | InChI=1S/C24H27NO7/c1-22(7-6-17(28)25-18-14(26)4-3-13(19(18)29)21(30)31)16(27)5-8-24-10-12-9-15(20(22)24)32-23(12,2)11-24/h3-5,8,12,15,20,26,29H,6-7,9-11H2,1-2H3,(H,25,28)(H,30,31)/t12-,15+,20+,22-,23+,24+/m1/s1 |
| SMILES | C[C@]12C[C@]34C[C@H]1C[C@@H]([C@H]3[C@](C(=O)C=C4)(C)CCC(=O)NC5=C(C=CC(=C5O)C(=O)O)O)O2 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Singh, Sheo B.; Jayasuriya, Hiranthi; Ondeyka, John G.; Herath, Kithsiri B.; Zhang, Chaowei; Zink, Deborah L.; Tsou, Nancy N.; Ball, Richard G.; Basilio, Angela; Genilloud, Olga; Diez, Maria Teresa; Vicente, Francisca; Pelaez, Fernando; Young, Katherine; Wang, Jun Isolation, structure, and absolute stereochemistry of platensimycin, a broad spectrum antibiotic discovered using an antisense differential sensitivity strategy Journal of the American Chemical Society 2006 128 (36) 11916-11920. | ||
|---|---|---|---|
| DOI | 10.1021/ja062232p | PMID | 16953632 |
SYNTHESES
| CITATION 1 | Eey ST; Lear MJ Total synthesis of (-)-platensimycin by advancing oxocarbenium- and iminium-mediated catalytic methods. Chemistry - A European Journal 2014 20 (36) 11556-11573. DOI: 10.1002/chem.201400131 PMID: 25047997 | ||
|---|---|---|---|
| CITATION 2 | Matsuo J; Takeuchi K; Ishibashi H Stereocontrolled formal synthesis of (+/-)-platensimycin. Organic Letters 2008 10 (18) 4049-4052. DOI: 10.1021/ol801584r PMID: 18702494 | ||
| CITATION 3 | Nicolaou KC; Li A; Edmonds DJ; Tria GS; Ellery SP Total synthesis of platensimycin and related natural products. Journal of the American Chemical Society 2009 131 (46) 16905-16918. DOI: 10.1021/ja9068003 PMID: 19874023 | ||
| CITATION 4 | Ghosh AK; Xi K Total synthesis of (-)-platensimycin, a novel antibacterial agent. Journal of Organic Chemistry 2009 74 (3) 1163-1170. DOI: 10.1021/jo802261f PMID: 19123842 | ||
| CITATION 5 | Nicolaou KC; Li A; Edmonds DJ Total synthesis of platensimycin. Angewandte Chemie International Edition 2006 45 (42) 7086-7090. DOI: 10.1002/anie.200603892 PMID: 17013803 | ||
| CITATION 6 | Nicolaou KC; Li A; Ellery SP; Edmonds DJ Rhodium-catalyzed asymmetric enyne cycloisomerization of terminal alkynes and formal total synthesis of (-)-platensimycin. Angewandte Chemie International Edition 2009 48 (34) 6293-6295. DOI: 10.1002/anie.200901992 PMID: 19606433 | ||
| CITATION 7 | Nicolaou KC; Tang Y; Wang J Formal synthesis of (+/-)-platensimycin. Chemical Communications 2007 (19) 1922-1923. DOI: 10.1039/b704589a PMID: 17695230 | ||
| CITATION 8 | Magnus P; Rivera H; Lynch V Concise formal total synthesis of platensimycin mediated by a stereoselective autoxidation and hydroxyl group directed conjugative reduction. Organic Letters 2010 12 (24) 5677-5679. DOI: 10.1021/ol102557k PMID: 21090652 | ||
