Tiacumicin F
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02697 |
| CAS | 106008-69-9 |
| Molecular Weight | 1058.04 |
| Molecular Formula | C52H74Cl2O18 |
Online Inquiry
Description
It is originally isolated from Dactylosporangium aurantiacum sub sp. hamdenensis sub sp. nov. AB718C-41. Tiacumicin C has the effect of resisting gram-positive bacteria. It also has the activity of inhibiting pathogenic Staphylococcus aureus and multi-dose drug-resistant bacteria.
Specification
| Synonyms | Clostomycin A; Benzoic acid, 3,5-dichloro-4,6-dihydroxy-2-ethyl-, 4'(3)-ester with 3-(((6-deoxy-2-O-methyl-beta-L-mannopyranosyl)oxy)methyl)-12-((6-deoxy-5-C-methyl-3-O-(2-methyl-1-oxopropyl)-beta-D-lyxo-hexopyranosyl)oxy)-11-ethyl-8-hydroxy-18-(1-hydroxyethyl)-9,13,15-trimethyloxacyclooctadeca-3,5,9,13,15-pentaen-2-one; Fidaxomicin Impurity 4 |
| IUPAC Name | [6-[[(3Z,5E,9E,13E,15E)-12-[3,5-dihydroxy-6,6-dimethyl-4-(2-methylpropanoyloxy)oxan-2-yl]oxy-11-ethyl-8-hydroxy-18-(1-hydroxyethyl)-9,13,15-trimethyl-2-oxo-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy]-4-hydroxy-5-methoxy-2-methyloxan-3-yl] 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate |
| Canonical SMILES | CCC1C=C(C(CC=CC=C(C(=O)OC(CC=C(C=C(C1OC2C(C(C(C(O2)(C)C)O)OC(=O)C(C)C)O)C)C)C(C)O)COC3C(C(C(C(O3)C)OC(=O)C4=C(C(=C(C(=C4O)Cl)O)Cl)CC)O)OC)O)C |
| InChI | InChI=1S/C52H74Cl2O18/c1-13-30-22-26(6)33(56)18-16-15-17-31(23-66-51-45(65-12)40(59)43(29(9)67-51)69-49(64)35-32(14-2)36(53)39(58)37(54)38(35)57)48(63)68-34(28(8)55)20-19-25(5)21-27(7)42(30)71-50-41(60)44(70-47(62)24(3)4)46(61)52(10,11)72-50/h15-17,19,21-22,24,28-30,33-34,40-46,50-51,55-61H,13-14,18,20,23H2,1-12H3/b16-15+,25-19+,26-22+,27-21+,31-17- |
| InChI Key | VYHICDMNVHVXOH-HSFUDZDJSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 1053.5°C at 760 mmHg |
| Melting Point | 141-143°C |
| Density | 1.33 g/cm3 |
Reference Reading
1. Synthesis of a Tiacumicin B Protected Aglycone
Louis Jeanne-Julien, Guillaume Masson, Eloi Astier, Grégory Genta-Jouve, Vincent Servajean, Jean-Marie Beau, Stéphanie Norsikian, Emmanuel Roulland Org Lett. 2017 Aug 4;19(15):4006-4009. doi: 10.1021/acs.orglett.7b01744. Epub 2017 Jul 19.
Tiacumicin B is an antibiotic endowed with the remarkable ability to interact with a new biological target, giving it an inestimable potential in the context of the ever-growing and worrisome appearance of resistances of bacteria and mycobacteria to antibiotics. The synthesis of an aglycone of tiacumicin B ready for glycosylation is reported. The key steps of this approach are a [2,3]-Wittig rearrangement, a Pd/Cu-catalyzed allene-alkyne cross-coupling, a E-selective cross-metathesis, and a final ring-size selective macrolactonization.
2. Study of the Construction of the Tiacumicin B Aglycone
Louis Jeanne-Julien, Guillaume Masson, Eloi Astier, Grégory Genta-Jouve, Vincent Servajean, Jean-Marie Beau, Stéphanie Norsikian, Emmanuel Roulland J Org Chem. 2018 Jan 19;83(2):921-929. doi: 10.1021/acs.joc.7b02909. Epub 2018 Jan 2.
Our study of the synthesis of the aglycone of tiacumicin B is discussed here. We imagined two possible strategies featuring a main retrosynthetic disconnection between C13 and C14. The first strategy was based on Suzuki-Miyaura cross-coupling of 1,1-dichloro-1-alkenes, but the failure of this pathway led us to use a Pd/Cu-dual-catalyzed cross-coupling of alkynes with allenes that had never been implemented before in a total synthesis context. We used density functional theory calculations to guide our strategic choices concerning a [2.3]-Wittig rearrangement step and the final ring-size selective Yamaguchi macrolactonization. This led to two syntheses of the aglycone of tiacumicin B, with one of last generation delivering ultimately an adequately protected and glycosylation-ready aglycone.
Recommended Products
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
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 ╳
