Baccatin III

Baccatin III
Names
	IUPAC name (2β,5α,7α,10α,13β)-4,10-Diacetoxy-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:32898;
ChEMBL	ChEMBL288043;
ChemSpider	23486966;
ECHA InfoCard	100.164.451
PubChem CID	65366;
CompTox Dashboard (EPA)	DTXSID301029474 ;
	SMILES CC1=C2[C@@H](C(=O)[C@@]3([C@@H](C[C@H]4[C@]([C@H]3[C@H]([C@@](C2(C)C)(C[C@H]1O)O)OC(=O)c5ccccc5)(CO4)OC(=O)C)O)C)OC(=O)C;
Properties
Chemical formula	C31H38O11
Molar mass	586.62677 Da
Melting point	229 to 234 °C (444 to 453 °F; 502 to 507 K)
Acidity (pKa)	12.76
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Baccatin III is an isolate of the Pacific yew tree (Taxus brevifolia) and related species. Baccatin III is a precursor to the anti-cancer drug paclitaxel (Taxol).

In 2014, researchers reported introduction and expression of the endophytic fungal gene responsible for synthesizing baccatin III (10-deacetylbaccatin III 10-O-acetyltransferase), to the mushroom Flammulina velutipes.^[1] Researchers achieved the same accomplishment with Escherichia coli in 2000.^[2]

References

^ Han F, Kang LZ, Zeng XL, Ye ZW, Guo LQ, Lin JF (2014). "Bioproduction of baccatin III, an advanced precursor of paclitaxol with transgenic Flammulina velutipes expressing 10-Deacetylbaccatin III-10-O-acetyl transferase gene". J Sci Food Agric. 94: 2376–2383. doi:10.1002/jsfa.6562. PMID 24403190.
^ Walker K, Croteau R (2000). "Molecular cloning of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli". Proc Natl Acad Sci U S A. 97 (2): 583–7. doi:10.1073/pnas.97.2.583. PMC 15373. PMID 10639122.

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[pmid24403190-1] Han F, Kang LZ, Zeng XL, Ye ZW, Guo LQ, Lin JF (2014). "Bioproduction of baccatin III, an advanced precursor of paclitaxol with transgenic Flammulina velutipes expressing 10-Deacetylbaccatin III-10-O-acetyl transferase gene". J Sci Food Agric. 94: 2376–2383. doi:10.1002/jsfa.6562. PMID 24403190.

[pmid10639122.-2] Walker K, Croteau R (2000). "Molecular cloning of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli". Proc Natl Acad Sci U S A. 97 (2): 583–7. doi:10.1073/pnas.97.2.583. PMC 15373. PMID 10639122.

[1]

[2]

See also

References