Baccatin III

Last updated
Baccatin III
Baccatin III.svg
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.164.451 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 636-675-9
KEGG
PubChem CID
UNII
  • InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,26-,29+,30-,31+/m0/s1
    Key: OVMSOCFBDVBLFW-VHLOTGQHSA-N
  • 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
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).

Baccatin III is an isolate from the yew tree (Genera Taxus ). 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]

See also

References

  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 (12): 2376–2383. Bibcode:2014JSFA...94.2376H. doi:10.1002/jsfa.6562. PMID   24403190.
  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. Bibcode:2000PNAS...97..583W. doi: 10.1073/pnas.97.2.583 . PMC   15373 . PMID   10639122.


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