Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA020338
PROPERTIES
| NPAID | NPA020338 |
|---|---|
| CLUSTER ID | 1004 |
| NODE ID | 866 |
| NAME | Pactamycin |
| FORMULA | C28H38N4O8 |
| MOLECULAR WEIGHT (Da) | 558.6320 |
| ACCURATE MASS (Da) | 558.2690 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | pactum |
| InChIKey | WVIUOSJLUCTGFK-JUJPXXQGSA-N |
| InChI | InChI=1S/C28H38N4O8/c1-15-9-7-12-20(35)21(15)24(36)40-14-27(39)23(30-19-11-8-10-18(13-19)16(2)33)22(29)28(17(3)34,26(27,4)38)31-25(37)32(5)6/h7-13,17,22-23,30,34-35,38-39H,14,29H2,1-6H3,(H,31,37)/t17-,22-,23-,26-,27+,28-/m0/s1 |
| SMILES | CC1=C(C(=CC=C1)O)C(=O)OC[C@]2([C@H]([C@@H]([C@]([C@@]2(C)O)([C@H](C)O)NC(=O)N(C)C)N)NC3=CC=CC(=C3)C(=O)C)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Wiley, PF; Jahnke, HK; MacKellar, FA; Kelly, BR; Argoudelis, AD Structure of pactamycin Journal of Organic Chemistry 1970 35 (5) 1420-1425. | ||
|---|---|---|---|
| DOI | 10.1021/jo00830a035 | PMID | 5440331 |
SYNTHESES
| CITATION 1 | Hanessian S; Vakiti RR; Dorich S; Banerjee S; Lecomte F; DelValle JR; Zhang J; Deschênes-Simard B Total synthesis of pactamycin. Angewandte Chemie International Edition 2011 50 (15) 3497-500. DOI: 10.1002/anie.201008079 PMID: 21370372 | ||
|---|---|---|---|
| CITATION 2 | Hanessian S; Vakiti RR; Dorich S; Banerjee S; Deschênes-Simard B Total synthesis of pactamycin and pactamycate: a detailed account. Journal of Organic Chemistry 2012 77 (21) 9458-72. DOI: 10.1021/jo301638z PMID: 23083207 | ||
| CITATION 3 | Malinowski JT; Sharpe RJ; Johnson JS Enantioselective synthesis of pactamycin, a complex antitumor antibiotic. Science 2013 340 (6129) 180-2. DOI: 10.1126/science.1234756 PMID: 23580525 | ||
| CITATION 4 | Kisunzu JK; Sarpong R Hidden symmetry enables a 15-step total synthesis of pactamycin. Angewandte Chemie International Edition 2013 52 (41) 10694-6. DOI: 10.1002/anie.201305464 PMID: 24039046 | ||
| CITATION 5 | Sharpe RJ; Malinowski JT; Johnson JS Asymmetric synthesis of the aminocyclitol pactamycin, a universal translocation inhibitor. Journal of the American Chemical Society 2013 135 (47) 17990-8. DOI: 10.1021/ja409944u PMID: 24245656 | ||
