10-Deacetylbaccatin

Chemical compound used in the synthesis of paclitaxel

10-Deacetylbaccatin III is a naturally occurring diterpene found in the yew tree, specifically in the Taxus species. It is a crucial intermediate in the semisynthesis of the anticancer drug paclitaxel, commonly known as Taxol.

Structure and Properties

10-Deacetylbaccatin III is a complex diterpene with a molecular formula of C31H38O10. It is characterized by its tetracyclic ring structure, which is a hallmark of the taxane family of compounds. The compound is named for the absence of an acetyl group at the C-10 position, distinguishing it from other related taxanes.

3D model of 10-Deacetylbaccatin III

Biosynthesis

10-Deacetylbaccatin III is biosynthesized in the Taxus species through a series of enzymatic reactions starting from the precursor geranylgeranyl pyrophosphate. The biosynthetic pathway involves multiple steps, including cyclization, oxidation, and acylation, leading to the formation of the taxane core structure.

Role in Paclitaxel Synthesis

10-Deacetylbaccatin III serves as a key starting material in the semisynthetic production of paclitaxel. The semisynthesis involves the attachment of a side chain to the C-13 position of the taxane core, which is essential for the biological activity of paclitaxel. This process allows for the large-scale production of paclitaxel, which is used in the treatment of various cancers, including ovarian cancer, breast cancer, and non-small cell lung cancer.

Extraction and Isolation

The compound is typically extracted from the needles and bark of the Taxus baccata and Taxus brevifolia species. The extraction process involves organic solvents and chromatographic techniques to isolate 10-Deacetylbaccatin III in its pure form. Due to the limited availability of natural sources, research into alternative methods of production, such as plant cell culture and biotechnological synthesis, is ongoing.

Applications in Research

Beyond its role in paclitaxel synthesis, 10-Deacetylbaccatin III is studied for its potential biological activities and as a scaffold for the development of novel taxane derivatives. Researchers are exploring modifications to the taxane core to enhance its pharmacological properties and reduce side effects associated with paclitaxel treatment.

Related pages

• Paclitaxel
• Taxane
• Diterpene
• Taxus

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  3D model of 10-Deacetylbaccatin