Pleuromutilin

Pleuromutilin (Pleuromutilin) ​​and its derivatives are antibacterial agents produced by fungi. Inhibit synthesis by binding to the () part of the () subunit.

Pleuromutilin - -

(4 R, 5 S, 6 S, 8 R, 9 a R, 10 R ) -6-Ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro- 3a, 9-propanocyclopenta [8] annulen-8-yl hydroxyacetate

Identification information | | | | | | |

• C [C @ H] 1 CC [C @ @] 23 CCC (= O) [C @ H] 2 ​​[C @ @] 1 ([C @ H] (C [C @ @] ([C @ H ] ([C @ H] 3 C) O) (C) C = C) OC (= O) CO) C

• InChI = 1 S / C 22 H 34 O 5 / c 1 - 6 - 20 (4) 11 - 16 (27 - 17 (25) 12 - 23) 21 (5) 13 (2) 7 - 9 - 22 (14 (3) 19 ) 26) 10-8-15 (24) 18 (21) 22 / h 6, 13 - 14, 16, 18 - 19, 23, 26 H, 1, 7 - 12 H 2, 2 - 5 H 3 / t 13 -, 14 +, 16 -, 18 +, 19 +, 20 -, 21 +, 22 + / m 1 / s 1 Key: ZRZNJUXESFHSIO - BKUNHTPHSA - N

InChI = 1 / C22H34O5 / c1-6-20 (4) 11-16 (27-17 (25) 12-23) 21 (5) 13 (2) 7-9-22 (14 (3) 19 (20) 26) 10 8 - 15 24 24 18/21, 22 - , 18 +, 19 +, 20 -, 21 +, 22 + / m 1 / s 1 Key: ZRZNJUXESFHSIO - BKUNHTPHBC

Characteristic | C22H34O5 | 378.5 g mol -1 Unless otherwise specified, data is at (25 ° C) · (100 kPa).

This class of antibiotics includes () () (for humans), (), (for use in animals) and clinical trials drugs (), () (BC - 3781) which are approved as medicines.

history

Pleuromutilin was first discovered as an antibiotic in 1951 and was made in the 1960s. Pleuromutilin is () (Clitopilus) It was isolated from Clitopilus passeckerianus (former scientific name is Pleurotus passeckerianus ), Drosophila subatrata , _ Clitopilus scyphoides _, and other lizards are also found in species of the genus Benitake.

Total synthesis

A number of pleuromutilins have been reported so far.

footnote

1. *Long, Katherine S; Lykke H. Hansen; Lene Jakobsen; Birte Vester (2006). _ Antimicrobial Agents and Chemotherapy *50(4): 1458 - 1462. 2. "*Lolk, L .; Pøhlsgaard, J .; Jepsen, AS; Hansen, LH; Nielsen, H .; Steffansen, SI; Sparving, L .; Nielsen, AB et al. Click Chemistry Approach to Pleuromutilin Conjugates with Nucleosides or Acyclic Nucleoside Derivatives and The Binding to the Bacterial Ribosome ". __*51(16): 4957 - 4967. 3. *Kavanagh, F .; Hervey, A. Robbins, W. J. (1951). Proc. Natl. Acad. Sci. U. S. A. *37: 570-574. 4. *Kavanagh, F .; Hervey, A. Robbins, W. J. (1952). Proc. Natl. Acad. Sci. U. S. A. *38: 555-560. 5. *Novak, R; Shlaes DM (2010). "The pleuromutilin antibiotics: a new class for human use". Current Opinion in Investigational Drugs *11(2): 182-91. 6. *Birch, A. J .; Cameron, D. W .; Holzapfel C. W .; Rickards, R. W .. "The diterpenoid nature of pleuromutilin". Chem. Ind. (London, U. K.) : 374. 7. *Birch, AJ; Holzapfel CW; Rickards, RW (1966). "The structure and some aspects of the biosynthesis of pleuromutilin." _ [[Tetrahedron (magazine) |]] _22S8): 359-387.:. 8. *Arigoni, D. (1968). "Some studies in the biosynthesis of terpenes and related compounds". Pure Appl. Chem. *17: 331 - 348. 9. *Kilaru, Sreedhar; Catherine M. Collins; Amanda J. Hartley; Andy M. Bailey; Gary D. Foster (2009-09-18).. _ _ Appp Environ Microbiol (American Society for Microbiology)*75(22): 7196-7204.:… 10. *Gibbons, E. G. (1982). "Total synthesis of (±) -pleuromutilin". __*104(6). 11. A stereocontrolled assembly of (±) -pleuromutilin via a remarkable sterically demanding oxy-11. *Boeckman, Jr. RK; Springer, DM; Alessi, TR (1989). "Synthetic studies directed toward naturally occurring cyclooctanoids. Cope rearrangement ". __*111(21): 8284 - 8286.:. 12. *Fazakerley, NJ; Helm, MD; Procter, DJ (2013). "Total Synthesis of (+) - Pleuromutilin". Chem. Eur. J. *19: 6718-6723.: . 13. *Murphy, S. K .; Zeng, M .; Herzon, S. B. (2017) "A modular and enantioselective synthesis of the pleuromutilin antibiotics" __*356(6341): 956-959.

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This article is taken from the Japanese Wikipedia Pleuromutilin

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