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Thiazinotrienomycin E

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Category Antibiotics
Catalog number BBF-03120
CAS 165337-97-3
Molecular Weight 709.89
Molecular Formula C38H51N3O8S

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Fermentation Lab

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Thiazinotrienomycin E is an ansa antibiotic produced by Str. sp. MJ672-m3. It has the effect of inhibiting cancer cells, and the IC50 for inhibiting HeLa cells is 13 ng/mL.

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IUPAC Name [(6E,8E,10E,16Z)-15,28-dihydroxy-5-methoxy-14,16-dimethyl-3,24-dioxo-22-thia-2,25-diazatricyclo[18.7.1.021,26]octacosa-1(27),6,8,10,16,20(28),21(26)-heptaen-13-yl] 2-(cyclohexanecarbonylamino)propanoate
Canonical SMILES CC1C(CC=CC=CC=CC(CC(=O)NC2=CC3=C(C(=C2O)CCC=C(C1O)C)SCC(=O)N3)OC)OC(=O)C(C)NC(=O)C4CCCCC4
InChI InChI=1S/C38H51N3O8S/c1-23-14-13-18-28-35(45)29(21-30-36(28)50-22-33(43)41-30)40-32(42)20-27(48-4)17-11-6-5-7-12-19-31(24(2)34(23)44)49-38(47)25(3)39-37(46)26-15-9-8-10-16-26/h5-7,11-12,14,17,21,24-27,31,34,44-45H,8-10,13,15-16,18-20,22H2,1-4H3,(H,39,46)(H,40,42)(H,41,43)/b6-5+,12-7+,17-11+,23-14-
InChI Key FZQITFWYBUDNRH-MHVOAVBDSA-N
Appearance White Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 887.3±65.0°C at 760 mmHg
Density 1.3±0.1 g/cm3
1. Thiazinotrienomycins, new ansamycin group antibiotics
N Hosokawa, H Naganawa, H Inuma, M Hamada, T Takeuchi, T Kanbe, M Hori J Antibiot (Tokyo). 1995 Jun;48(6):471-8. doi: 10.7164/antibiotics.48.471.
New triene-ansamycins designated thiazinotrienomycins A, B, C, D and E were isolated from culture broth of Streptomyces sp. MJ672-m3 for their activities against cervical cancer cell lines. The structures and some biological and biochemical properties of the antibiotics were determined.
2. Total synthesis of the ansamycin antibiotic (+)-thiazinotrienomycin E
A B Smith rd, Z Wan J Org Chem. 2000 Jun 16;65(12):3738-53. doi: 10.1021/jo991958j.
The first total synthesis of (+)-thiazinotrienomycin E (1), member of a novel class of cytotoxic ansamycin antibiotics, has been achieved. Key features of the synthetic strategy include (a) the efficient construction of sulfone 7 incorporating TBS protection of the aniline, (b) an improved synthesis of allyl chloride (-)-6, the advanced intermediate employed in our trienomycins A and F total syntheses, (c) application of the Kocienski modified Julia protocol to elaborate the E,E,E-triene subunit in a stereo-controlled fashion, (d) an efficient union of sulfone 7 with advanced iodide 62, and (e) Mukaiyama macrolactamization to access the thiazinotrienomycin macrocyclic ring.
3. Total synthesis of (+)-thiazinotrienomycin E
A B Smith rd, Z Wan Org Lett. 1999 Nov 4;1(9):1491-4. doi: 10.1021/ol991049g.
[formula: see text] The first total synthesis of (+)-thiazinotrienomycin E (1), member of a novel class of cytotoxic ansamycin antibiotics, has been achieved. The synthesis features a highly efficient construction of the aromatic fragment 3 incorporating TBS protection of the aniline, a significantly improved synthesis of (-)-19, an intermediate employed in our trienomycins A and F total syntheses, application of the Kocienski modified Julia protocol to elaborate the E,E,E-triene subunit, an efficient union of 3 and (+)-4, and Mukaiyama macrolactamization to access the thiazinotrienomycin macrolide.

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