Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA011087
PROPERTIES
| NPAID | NPA011087 |
|---|---|
| CLUSTER ID | 4338 |
| NODE ID | 3193 |
| NAME | Borrelidin |
| FORMULA | C28H43NO6 |
| MOLECULAR WEIGHT (Da) | 489.6530 |
| ACCURATE MASS (Da) | 489.3090 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | rochei |
| InChIKey | OJCKRNPLOZHAOU-UGKRXNSESA-N |
| InChI | InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1 |
| SMILES | C[C@H]1C[C@H](C[C@@H]([C@H](/C(=C\C=C\C[C@H](OC(=O)C[C@@H]([C@H](C1)C)O)[C@@H]2CCC[C@H]2C(=O)O)/C#N)O)C)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Keller‐Schierlein, W Metabolic products of microorganisms. Concerning the constitution of borrelidin Helvetica Chimica Acta 1967 50 (3) 731-753. | ||
|---|---|---|---|
| DOI | 10.1002/hlca.19670500303 | PMID | 5584833 |
SYNTHESES
| CITATION 1 | Hanessian S; Yang Y; Giroux S; Mascitti V; Ma J; Raeppel F Application of conformation design in acyclic stereoselection: total synthesis of borrelidin as the crystalline benzene solvate. Journal of the American Chemical Society 2003 125 (45) 13784-13792. DOI: 10.1021/ja030139k PMID: 14599218 | ||
|---|---|---|---|
| CITATION 2 | Vong BG; Kim SH; Abraham S; Theodorakis EA Stereoselective total synthesis of (-)-borrelidin. Angewandte Chemie International Edition 2004 43 (30) 3947-3951. DOI: 10.1002/anie.200460203 PMID: 15274222 | ||
| CITATION 3 | Madduri AV; Minnaard AJ Formal synthesis of the anti-angiogenic polyketide (-)-borrelidin under asymmetric catalytic control. Chemistry - A European Journal 2010 16 (38) 11726-11731. DOI: 10.1002/chem.201001284 PMID: 20734306 | ||
| CITATION 4 | Nagamitsu T; Takano D; Marumoto K; Fukuda T; Furuya K; Otoguro K; Takeda K; Kuwajima I; Harigaya Y; Omura S Total synthesis of borrelidin. Journal of Organic Chemistry 2007 72 (8) 2744-2756. DOI: 10.1021/jo062089i PMID: 17355148 | ||
| CITATION 5 | Herber C; Breit B Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution: formal total synthesis of borrelidin (C3-C11 fragment). Chemistry - A European Journal 2006 12 (25) 6684-6691. DOI: 10.1002/chem.200600343 PMID: 16773665 | ||
| CITATION 6 | Nagamitsu T; Takano D; Fukuda T; Otoguro K; Kuwajima I; Harigaya Y; Omura S Total synthesis of (-)-borrelidin. Organic Letters 2004 6 (11) 1865-1867. DOI: 10.1021/ol049356w PMID: 15151434 | ||
| CITATION 7 | Duffey MO; LeTiran A; Morken JP Enantioselective total synthesis of borrelidin. Journal of the American Chemical Society 2003 125 (6) 1458-1459. DOI: 10.1021/ja028941u PMID: 12568588 | ||
