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10-Deacetylbaccatin III

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Ramesh N. Patel – 1st expert on this subject based on the ideXlab platform

  • Conversion of 7-deoxy-10-DeacetylbaccatinIII into 6-alpha-hydroxy-7-deoxy-10-DeacetylbaccatinIII by Nocardioides luteus.
    Biotechnology and applied biochemistry, 2020
    Co-Authors: Ronald L Hanson, Joydeep Kant, Ramesh N. Patel

    Abstract:

    6-alpha-Hydroxy-7-deoxy-10-DeacetylbaccatinIII is an intermediate that is potentially useful for synthesis of analogues of paclitaxel. Screening of microbial strains identified an enzyme activity in Nocardioides luteus SC 13912 (A.T.C.C. 55426) which converted 7-deoxy-10-DeacetylbaccatinIII into 6-hydroxy-7-deoxy-10-DeacetylbaccatinIII with a maximum yield of 44%.

  • Enzymatic C-4 deacetylation of 10-Deacetylbaccatin III.
    Biotechnology and applied biochemistry, 2020
    Co-Authors: Ronald L Hanson, William L Parker, Ramesh N. Patel

    Abstract:

    Second-generation paclitaxel analogues that require replacement of the C-4 acetate by other substituents are in development. An enzyme able to specifically remove the C-4 acetate from paclitaxel could simplify preparation of the analogues. Several strains were isolated from soil samples that contain enzyme activities able to 4-deacetylate 10-DAB (10-Deacetylbaccatin III). Selection was made using plates containing 10-DAB as the sole carbon source and screening colonies for deacetylation of 10-DAB. Two strains initially isolated were identified as Rhodococcus sp. and deposited with the A.T.C.C. (Manassas, VA, U.S.A.) as strains 202191 and 202192. Whole cells were able to convert 10-DAB into 4,10-DDAB (4-deacetyl-10-Deacetylbaccatin III) in 90% yield. The enzyme activity in these strains was not effective with paclitaxel and 10-deacetylpaclitaxel, although 4,10-DDAB was produced from baccatin III. The activity in these strains was associated with an insoluble fraction of cell extracts. Several additional isolates were obtained that were identified as variants of Stenotrophomonas maltophilia, and a soluble C-4 deacetylase was purified approx. 218-fold from one of them. The activity of this enzyme was limited to 10-DAB, and the enzyme was not effective with paclitaxel or baccatin III.

  • Conversion of 7-deoxy- 10-DeacetylbaccatinIII into 6-α-hydroxy-7-deoxy-10-DeacetylbaccatinIII by Nocardioides luteus
    Biotechnology and Applied Biochemistry, 2004
    Co-Authors: Ronald L Hanson, Joydeep Kant, Ramesh N. Patel

    Abstract:

    6-α-Hydroxy-7-deoxy-10-DeacetylbaccatinIII is an intermediate that is potentially useful for synthesis of analogues of paclitaxel. Screening of microbial strains identified an enzyme activity in Nocardioides luteus SC 13912 (A.T.C.C. 55426) which converted 7-deoxy-10-DeacetylbaccatinIII into 6-hydroxy-7-deoxy-10-de-acetylbaccatin-III with a maximum yield of 44%.

Ezio Bombardelli – 2nd expert on this subject based on the ideXlab platform

  • Microbial transformation of 10-Deacetylbaccatin III (10-DAB) by Curvularia lunata and Trametes hirsuta
    Journal of Molecular Catalysis B-enzymatic, 2006
    Co-Authors: Alberto Arnone, Ezio Bombardelli, Adriana Bava, Stefano Alemani, Gianluca Nasini, Gabriele Fontana

    Abstract:

    Abstract The microbial transformation of 10-Deacetylbaccatin III (10-DAB) ( 1a ) and 13-DeBAC ( 4b ) was investigated. Trametes hirsuta induced 13-oxidation of 10-DAB to give ( 4a ) in high yield, whereas incubation with Curvularia lunata resulted in the isolation of the 7- epi -10-DAB ( 2 ) and the 7- epi -10-oxo-10-DAB ( 3 ). 13-DeBAC ( 4b ) was biotransformed into compounds ( 4a ) and ( 4c ) by Alternaria alternata .

  • Synthesis and biological evaluation of methoxylated analogs of the newer generation taxoids IDN5109 and IDN5390.
    Bioorganic & Medicinal Chemistry Letters, 2005
    Co-Authors: Luciano Barboni, Giovanni Appendino, Gabriele Fontana, Roberto Ballini, Guido Giarlo, Ezio Bombardelli

    Abstract:

    Starting from 10-Deacetylbaccatin III (7), the 2-debenzoyl-2-m-methoxybenzoyl analogs of the newer generation taxoids IDN5109 (3) and IDN5390 (4) were synthesized. The biological evaluation of these compounds (5 and 6, respectively) showed a general increase of cytotoxicity, as observed in first-generation anticancer taxanes.

  • Diastereoselective 14β-Hydroxylation of Baccatin III Derivatives
    Journal of Organic Chemistry, 2003
    Co-Authors: Eleonora Baldelli, Ezio Bombardelli, Gabriele Fontana, Arturo Battaglia, Giacomo Carenzi, Andrea Gambini, Maria Luisa Gelmi, A. Guerrini, Donato Pocar

    Abstract:

    14β-Hydroxybaccatin III, a compound with limited availability by natural sources, is the starting material for the synthesis of the second-generation anticancer taxoid ortataxel. The 7-tert-butoxycarbonyl (1a) and 7-triethylsilyl (1b) derivatives of 14β-hydroxybaccatin III 1,14-carbonate were synthesized from 10-Deacetylbaccatin III (3). The crucial steps were (a) the C14β hydroxylation of the corresponding 13-oxobaccatin III derivatives by oxaziridine-mediated electrophilic oxidation and (b) the reduction of the C13 carbonyl group with sodium or alkylammonium borohydrides. This protocol provides a practical way for the semisynthesis of ortataxel from 10-Deacetylbaccatin III, a compound readily available from various yews.

Joëlle Dubois – 3rd expert on this subject based on the ideXlab platform

  • Semisynthesis and biological evaluation of a novel D-seco docetaxel analogue.
    Organic Letters, 2006
    Co-Authors: Sylviane Thoret, Francoise Gueritte, Daniel Guénard, Joëlle Dubois

    Abstract:

    A 4-methyl-5-oxo docetaxel analogue has been prepared starting from 10-Deacetylbaccatin III. This new D-seco docetaxel analogue is slightly less potent than docetaxel at microtubule stabilization in vitro and has about 1/1000th the cytotoxicity of docetaxel. The lack of improved activity for this compound compared to other D-modified taxoids confirms that a C-5 oxygen atom is not required for biological activity.

  • Semisynthesis and biological evaluation of a novel D-seco docetaxel analogue
    Organic Letters, 2006
    Co-Authors: Sylviane Thoret, Francoise Gueritte, Daniel Guénard, Joëlle Dubois

    Abstract:

    [reaction: see text] A 4-methyl-5-oxo docetaxel analogue has been prepared starting from 10-Deacetylbaccatin III. This new D-seco docetaxel analogue is slightly less potent than docetaxel at microtubule stabilization in vitro and has about 1/1000th the cytotoxicity of docetaxel. The lack of improved activity for this compound compared to other D-modified taxoids confirms that a C-5 oxygen atom is not required for biological activity.

  • Deletion of the oxetane ring in docetaxel analogues: synthesis and biological evaluation.
    Organic Letters, 2003
    Co-Authors: Vaishali Deka, Sylviane Thoret, Joëlle Dubois, Francoise Gueritte, Daniel Guénard

    Abstract:

    Two new docetaxel analogues have been prepared starting from 10-Deacetylbaccatin III. Both derivatives lack the oxetane D-ring but possess the 4α-acetoxy group, which is important for biological activity. The influence of a more or less constrained C-ring was evaluated by adding, or not adding, a double bond in this ring. Both compounds were found to be equally less active than docetaxel in biological assays.