Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA020681
PROPERTIES
| NPAID | NPA020681 |
|---|---|
| CLUSTER ID | 6499 |
| NODE ID | 4496 |
| NAME | Lactacystin |
| FORMULA | C15H24N2O7S |
| MOLECULAR WEIGHT (Da) | 376.4310 |
| ACCURATE MASS (Da) | 376.1304 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | sp. OM-6519 |
| InChIKey | DAQAKHDKYAWHCG-RWTHQLGUSA-N |
| InChI | InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10+,11+,15-/m1/s1 |
| SMILES | C[C@@H]1[C@@H]([C@](NC1=O)([C@H](C(C)C)O)C(=O)SC[C@@H](C(=O)O)NC(=O)C)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Omura S; Fujimoto T; Otoguro K; Matsuzaki K; Moriguchi R; Tanaka H; Sasaki Y LACTACYSTIN, A NOVEL MICROBIAL METABOLITE, INDUCES NEURITOGENESIS OF NEUROBLASTOMA CELLS Journal of Antibiotics 1991 44 (1) 113-116. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.44.113 | PMID | 1848215 |
SYNTHESES
| CITATION 1 | Corey EJ; Li WD Total synthesis and biological activity of lactacystin, omuralide and analogs. Chemical and Pharmaceutical Bulletin 1999 47 (1) 1-10. DOI: 10.1248/cpb.47.1 PMID: 9987821 | ||
|---|---|---|---|
| CITATION 2 | Fukuda N; Sasaki K; Sastry TV; Kanai M; Shibasaki M Catalytic asymmetric total synthesis of (+)-lactacystin. Journal of Organic Chemistry 2006 71 (3) 1220-5. DOI: 10.1021/jo0524223 PMID: 16438540 | ||
| CITATION 3 | Balskus EP; Jacobsen EN Alpha,beta-unsaturated beta-silyl imide substrates for catalytic, enantioselective conjugate additions: a total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor. Journal of the American Chemical Society 2006 128 (21) 6810-2. DOI: 10.1021/ja061970a PMID: 16719460 | ||
| CITATION 4 | Shibasaki M; Kanai M; Fukuda N Total synthesis of lactacystin and salinosporamide A. Chemistry - An Asian Journal 2007 2 (1) 20-38. DOI: 10.1002/asia.200600310 PMID: 17441136 | ||
| CITATION 5 | Panek JS; Masse CE Total synthesis of (+)-lactacystin. Angewandte Chemie International Edition 1999 38 (8) 1093-5. DOI: 10.1002/(SICI)1521-3773(19990419)38:8<1093::AID-ANIE1093>3.0.CO;2-U PMID: 25138505 | ||
| CITATION 6 | Yoshioka S; Nagatomo M; Inoue M Application of two direct C(sp3)-H functionalizations for total synthesis of (+)-lactacystin. Organic Letters 2015 17 (1) 90-3. DOI: 10.1021/ol503291s PMID: 25526222 | ||
| CITATION 7 | Corey EJ; Li W; Nagamitsu T An Efficient and Concise Enantioselective Total Synthesis of Lactacystin. Angewandte Chemie International Edition 1998 37 (12) 1676-1679. DOI: 10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T PMID: 29711503 | ||
| CITATION 8 | Nagatomo M [Development of Synthetic Strategies for Densely Oxygenated Natural Products: Total Synthesis of Lactacystin and Zaragozic Acid C Using Photochemical C(sp Yakugaku Zasshi 2019 139 (5) 651-661. DOI: 10.1248/yakushi.18-00210 PMID: 31061332 | ||
