Tiacumicin A
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| Category | Antibiotics |
| Catalog number | BBF-02695 |
| CAS | 109713-94-2 |
| Molecular Weight | 604.77 |
| Molecular Formula | C34H52O9 |
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Description
It is originally isolated from Dactylosporangium aurantiacum sub sp. hamdenensis subsp. nov. AB718C-41. Tiacumicin A has the effect of resisting gram-positive bacteria.
Specification
| IUPAC Name | [(3R,4R,5S,6R)-6-[[(4E,6E,10E,14Z,16E)-2,9-diethyl-12-hydroxy-5,7,11,17-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,10,14,16-pentaen-8-yl]oxy]-4,5-dihydroxy-2,2-dimethyloxan-3-yl] acetate |
| Canonical SMILES | CCC1CC=C(C=C(C(C(C=C(C(CC=CC=C(C(=O)O1)C)O)C)CC)OC2C(C(C(C(O2)(C)C)OC(=O)C)O)O)C)C |
| InChI | InChI=1S/C34H52O9/c1-10-25-19-22(5)27(36)15-13-12-14-21(4)32(39)41-26(11-2)17-16-20(3)18-23(6)30(25)42-33-29(38)28(37)31(40-24(7)35)34(8,9)43-33/h12-14,16,18-19,25-31,33,36-38H,10-11,15,17H2,1-9H3/b13-12-,20-16+,21-14+,22-19+,23-18+/t25?,26?,27?,28-,29+,30?,31-,33-/m1/s1 |
| InChI Key | XUIZTHTZQXQZGN-LHXYLVPQSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
Reference Reading
1. Tiacumicin Congeners with Improved Antibacterial Activity from a Halogenase-Inactivated Mutant
Haibo Zhang, Xiaoxing Tian, Xiaohui Pu, Qingbo Zhang, Wenjun Zhang, Changsheng Zhang J Nat Prod. 2018 May 25;81(5):1219-1224. doi: 10.1021/acs.jnatprod.7b00990. Epub 2018 Apr 20.
Tiacumicin B (1, also known as fidaxomicin or difimicin) is a marketed drug for the treatment of Clostridium difficile infections. The biosynthetic pathway of 1 has been studied in Dactylosporangium aurantiacum subsp. hamdenensis NRRL 18085 and has enabled the identification of TiaM as a tailoring dihalogenase. Herein we report the isolation, structure elucidation, and bioactivity evaluation of 14 tiacumicin congeners (including 11 new ones) from the tiaM-inactivated mutant. A new tiacumicin congener, 3, with a propyl group at C-7‴ of the aromatic ring was found to exhibit improved antibacterial activity.
2. Total Synthesis of Tiacumicin A. Total Synthesis, Relay Synthesis, and Degradation Studies of Fidaxomicin (Tiacumicin B, Lipiarmycin A3)
Hiromu Hattori, Elias Kaufmann, Hideki Miyatake-Ondozabal, Regina Berg, Karl Gademann J Org Chem. 2018 Jul 6;83(13):7180-7205. doi: 10.1021/acs.joc.8b00101. Epub 2018 Apr 12.
The commercial macrolide antibiotic fidaxomicin was synthesized in a highly convergent manner. Salient features of this synthesis include a β-selective noviosylation, a β-selective rhamnosylation, a ring-closing metathesis, a Suzuki coupling, and a vinylogous Mukaiyama aldol reaction. Careful choice of protecting groups and fine-tuning of the glycosylation reactions led to the first total synthesis of fidaxomicin. In addition, a relay synthesis of fidaxomicin was established, which gives access to a conveniently protected intermediate from the natural material for derivatization. The first total synthesis of a related congener, tiacumicin A, is presented.
3. Total Synthesis of Tiacumicin B: Study of the Challenging β-Selective Glycosylations*
Cédric Tresse, Marc François-Heude, Vincent Servajean, Rubal Ravinder, Clémence Lesieur, Lucie Geiben, Louis Jeanne-Julien, Vincent Steinmetz, Pascal Retailleau, Emmanuel Roulland, Jean-Marie Beau, Stéphanie Norsikian Chemistry. 2021 Mar 17;27(16):5230-5239. doi: 10.1002/chem.202005102. Epub 2021 Feb 18.
We give a full account of the total synthesis of tiacumicin B (Tcn-B), a natural glycosylated macrolide with remarkable antibiotic properties. Our strategy is based on our experience with the synthesis of the tiacumicin B aglycone and on unique 1,2-cis-glycosylation steps. We used sulfoxide anomeric leaving-groups in combination with a remote 3-O-picoloyl group on the donors that allowed highly β-selective rhamnosylation and noviosylation that rely on H-bond-mediated aglycone delivery. The rhamnosylated C1-C3 fragment was anchored to the C4-C19 aglycone fragment by a Suzuki-Miyaura cross-coupling. Ring-size-selective Shiina macrolactonization provided a semiglycosylated aglycone that was engaged directly in the noviolysation step with a virtually total β-selectivity. Finally, a novel deprotection method was devised for the removal of a 2-naphthylmethyl ether on a phenol, and efficient removal of all the protecting groups provided synthetic tiacumicin B.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
