Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA002819
PROPERTIES
| NPAID | NPA002819 |
|---|---|
| CLUSTER ID | 1635 |
| NODE ID | 1340 |
| NAME | Zwittermicin A |
| FORMULA | C13H28N6O8 |
| MOLECULAR WEIGHT (Da) | 396.4010 |
| ACCURATE MASS (Da) | 396.1969 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Bacillus |
| ORIGIN SPECIES | cereus (UW85) |
| InChIKey | FYIPKJHNWFVEIR-VTAUKWRXSA-N |
| InChI | InChI=1S/C13H28N6O8/c14-4(3-20)6(21)1-7(22)8(15)9(23)10(24)12(26)19-5(11(16)25)2-18-13(17)27/h4-10,20-24H,1-3,14-15H2,(H2,16,25)(H,19,26)(H3,17,18,27)/t4-,5-,6+,7+,8+,9+,10-/m0/s1 |
| SMILES | NC(=O)NC[C@H](NC(=O)[C@@H](O)[C@H](O)[C@H](N)[C@H](O)C[C@@H](O)[C@@H](N)CO)C(N)=O |
ORIGINAL ISOLATION REFERENCE
| CITATION | He, Haiyin; Silo-Suh, Laura A.; Handelsman, Jo; Clardy, Jon Zwittermicin A, an antifungal and plant protection agent from Bacillus cereus Tetrahedron Letters 1994 35 (16) 2499-2502. | ||
|---|---|---|---|
| DOI | 10.1016/s0040-4039(00)77154-1 | PMID | - |
SYNTHESES
| CITATION 1 | Rogers EW; Dalisay DS; Molinski TF (+)-Zwittermicin A: assignment of its complete configuration by total synthesis of the enantiomer and implication of D-serine in its biosynthesis. Angewandte Chemie International Edition 2008 47 (42) 8086-8089. DOI: 10.1002/anie.200801561 PMID: 18798190 | ||
|---|---|---|---|
| CITATION 2 | Rogers EW; Molinski TF (+)-Zwittermicin A. Rapid assembly of C9-C15 and a formal total synthesis. Journal of Organic Chemistry 2009 74 (20) 7660-7664. DOI: 10.1021/jo901007v PMID: 19746943 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C(C([C@H]([C@H]([C@@H](C(=O)NC(CNC(=O)N)C(=O)N)O)O)N)O)C(C(CO)N)O | He, Haiyin; Silo-Suh, Laura A.; Handelsman, Jo; Clardy, Jon Zwittermicin A, an antifungal and plant protection agent from Bacillus cereus Tetrahedron Letters 1994 35 (16) 2499-2502. DOI: 10.1016/s0040-4039(00)77154-1 | ||
| 2 | NC(=O)NC[C@H](NC(=O)[C@@H](O)[C@H](O)[C@H](N)[C@H](O)C[C@@H](O)[C@@H](N)CO)C(N)=O | Rogers, Evan W; Molinski, Tadeusz F Asymmetric synthesis of diastereomeric diaminoheptanetetraols. A proposal for the configuration of (+)-zwittermicin a. Organic Letters 2007 9 (3) 437-40. DOI: 10.1021/ol062804a PMID: 17249781 | ||
