Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA004995
PROPERTIES
| NPAID | NPA004995 |
|---|---|
| CLUSTER ID | 2513 |
| NODE ID | 1971 |
| NAME | TMG-chitotriomycin |
| FORMULA | C33H59N4O20+ |
| MOLECULAR WEIGHT (Da) | 831.8430 |
| ACCURATE MASS (Da) | 831.3717 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | anulatus NBRC 13369 |
| InChIKey | WQUCMKJYZLSZGP-PYEDOYKNSA-O |
| InChI | InChI=1S/C33H58N4O20/c1-11(42)34-18-23(46)27(15(8-39)51-30(18)50)55-31-19(35-12(2)43)24(47)28(16(9-40)53-31)56-32-20(36-13(3)44)25(48)29(17(10-41)54-32)57-33-21(37(4,5)6)26(49)22(45)14(7-38)52-33/h14-33,38-41,45-50H,7-10H2,1-6H3,(H2-,34,35,36,42,43,44)/p+1/t14-,15-,16-,17-,18?,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30?,31+,32+,33-/m1/s1 |
| SMILES | CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)NC(=O)C)O[C@@H]3[C@H](OC(C([C@H]3O)NC(=O)C)O)CO)CO)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)[N+](C)(C)C)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Usuki, Hirokazu; Nitoda, Teruhiko; Ichikawa, Misato; Yamaji, Nahoko; Iwashita, Takashi; Komura, Hajime; Kanzaki, Hiroshi TMG-chitotriomycin, an enzyme inhibitor specific for insect and fungal β-N-acetylglucosaminidases, produced by actinomycete Streptomyces anulatus NBRC 13369 Journal of the American Chemical Society 2008 130 (12) 4146-4152. | ||
|---|---|---|---|
| DOI | 10.1021/ja077641f | PMID | 18307344 |
SYNTHESES
| CITATION 1 | Yang Y; Li Y; Yu B Total synthesis and structural revision of TMG-chitotriomycin, a specific inhibitor of insect and fungal beta-N-acetylglucosaminidases. Journal of the American Chemical Society 2009 131 (34) 12076-12077. DOI: 10.1021/ja9055245 PMID: 19663423 | ||
|---|---|---|---|
| CITATION 2 | Isoda Y; Sasaki N; Kitamura K; Takahashi S; Manmode S; Takeda-Okuda N; Tamura JI; Nokami T; Itoh T Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block. Beilstein Journal of Organic Chemistry 2017 13 919-924. DOI: 10.3762/bjoc.13.93 PMID: 28684973 | ||
