71629-92-0Relevant articles and documents
Biological degradation of taxol by action of cultured cells on 7-acetyltaxol-2″-yl glucoside
Shimoda, Kei,Mikuni, Katsuhiko,Nakajima, Kiyoshi,Hamada, Hatsuyuki,Hamada, Hiroki
, p. 362 - 363 (2008/09/20)
Biodegradation pathways of taxol in cultured cells of Synechocystis sp. PCC 6803, Synechococcus sp. PCC 7942, Marchantia polymorpha, Nicotiana tabacum, and Glycine max were investigated using a water-soluble taxol derivative, 7-ace-tyltaxol-2″-yl glucoside, as the substrate. Although cyanobacteria, Synechocystis sp. PCC 6803 and Synechococcus sp. PCC 7942, and a lower plant, M. polymorpha, catalyzed the epimerization at 7-position of taxol skeleton, no epimerization occurred with higher plants, N. tabacum and G. max. On the other hand, Synechocystis sp. PCC 6803, Synechococcus sp. PCC 7942, M. polymorpha, and N. tabacum catalyzed hydrolysis at 13-position of taxol to give baccatin III and 10-deacetyl baccatin III. Both cyanobacteria cells also deacetylated 7-epi-baccatin III at its 10-position. M. polymorpha and G. max deacetylated at 10-position of taxol. Copyright
The chemistry of the taxane diterpene: Stereoselective reductions of taxanes
Georg, Gunda I.,Harriman, Geraldine C. B.,Datta, Apurba,Ali, Syed,Cheruvallath, Zacharia,Dutta, Dinah,Vander Velde, David G.,Himes, Richard H.
, p. 8926 - 8934 (2007/10/03)
Stereoselective reductions of taxanes are detailed. Chelation- controlled reductions employing SmI2 are described for the stereoselective reduction of the 9-keto functionality of the diterpene moiety of several taxanes. In all cases the 9β-hydr
THE CHEMISTRY OF TAXANES: REACTIONS OF TAXOL AND BACCATIN DERIVATIVES WITH LEWIS ACIDS IN APROTIC AND PROTIC MEDIA
Chen, Shu-Hui,Huang, Stella,Wei, Jianmei,Farina, Vittorio
, p. 2805 - 2828 (2007/10/02)
Several Lewis acids were shown to cleanyl open the oxetane ring of taxol and baccatin derivatives.The reaction is shown to proceed via anchimeric assistance by the C-4 acetate group.Several minor products, including a novel derivative possessing a bridged C-ring, were also isolated.A mechanistric rationale is provides for all compounds formed.When taxol derivatives were treated with Lewis acids in methanol, ester cleavage reactions were observed.We provide conditions that are selective for C-10 acetate cleavage and for C-13 side-chain methanolysis.