baccatin iii (MedChemExpress)
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baccatin iii
![a , Heat map showing the ranks of new T9αH and T1βHs and other Taxol biosynthetic genes in the <t>three</t> modules. T9αH-725A is the T9αH independently reported by other groups – . Black, previously known Taxol genes. Orange, new Taxol pathway genes identified in this figure. Red, Taxus enzymes proposed to act in other taxane pathways. b , Proposed biosynthetic pathway from 4 , the latest intermediate we reported recently , to taxusin ( 6 ), and the corresponding extracted ion chromatograms (EICs) of products 4 – 6 when the indicated sets of genes were expressed in N. benthamiana leaves. Blue shading highlights the biosynthetic pathway towards Taxol, which only involves 4 and 5 . c , Proposed biosynthetic pathway from 5 to <t>baccatin</t> VI ( 11-Bz ), and the corresponding EICs of intermediates when the indicated sets of genes were expressed in N. benthamiana leaves. Blue shading highlights the biosynthetic pathway towards Taxol. Structures of 5 , 7-Ac , 7-Bz , 8-Ac , 8-Bz , 9-Ac , 9-Bz , 10-Ac , 10-Bz and 11-Ac are proposed on the basis of the functions of enzymes previously characterized (TAT, TAX19, T2αH, TBT, T7βH and TOT) and described in this study (Τ9αH-750C, T7AT and T1βH). TAX19 is used to generate known 13- O -acetylated products, including taxusin ( 6 ) and baccatin VI ( 11-Bz ), for structural analysis. Diamond indicates the structure is supported by NMR. d , EICs of expected products when the pathway to 6O4A is expressed with TOT, T7AT or both in N. benthamiana . In the absence of T7AT, no notable 6O4A depletion or product formation by TOT is observed. e , MS/MS fragmentation patterns of heterologously produced baccatin VI ( 11-Bz ) in N. benthamiana compared with that of 11-Bz standard. MS/MS fragmentations were generated using [M+Na] + ( m / z = 737.2788) as the precursor ion and fragmented with a collision energy of 30 eV.](https://pub-med-central-images-cdn.bioz.com/pub_med_central_ids_ending_with_0809/pmc12240809/pmc12240809__41586_2025_9090_Fig4_HTML.jpg)
Baccatin Iii, supplied by MedChemExpress, used in various techniques. Bioz Stars score: 93/100, based on 2 PubMed citations. ZERO BIAS - scores, article reviews, protocol conditions and more
https://www.bioz.com/product/hy-n6985/Baccatin+III/pmc12240809-243-30-32
Average 93 stars, based on 2 article reviews
Baccatin Iii, supplied by MedChemExpress, used in various techniques. Bioz Stars score: 93/100, based on 2 PubMed citations. ZERO BIAS - scores, article reviews, protocol conditions and more
https://www.bioz.com/product/hy-n6985/Baccatin+III/pmc12240809-243-30-32
Average 93 stars, based on 2 article reviews
baccatin iii - by Bioz Stars,
2026-10
93/100 stars
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1) Product Images from "Discovery of FoTO1 and Taxol genes enables biosynthesis of baccatin III"
Article Title: Discovery of FoTO1 and Taxol genes enables biosynthesis of baccatin III
Journal: Nature
doi: 10.1038/s41586-025-09090-z
Figure Legend Snippet: a , Heat map showing the ranks of new T9αH and T1βHs and other Taxol biosynthetic genes in the three modules. T9αH-725A is the T9αH independently reported by other groups – . Black, previously known Taxol genes. Orange, new Taxol pathway genes identified in this figure. Red, Taxus enzymes proposed to act in other taxane pathways. b , Proposed biosynthetic pathway from 4 , the latest intermediate we reported recently , to taxusin ( 6 ), and the corresponding extracted ion chromatograms (EICs) of products 4 – 6 when the indicated sets of genes were expressed in N. benthamiana leaves. Blue shading highlights the biosynthetic pathway towards Taxol, which only involves 4 and 5 . c , Proposed biosynthetic pathway from 5 to baccatin VI ( 11-Bz ), and the corresponding EICs of intermediates when the indicated sets of genes were expressed in N. benthamiana leaves. Blue shading highlights the biosynthetic pathway towards Taxol. Structures of 5 , 7-Ac , 7-Bz , 8-Ac , 8-Bz , 9-Ac , 9-Bz , 10-Ac , 10-Bz and 11-Ac are proposed on the basis of the functions of enzymes previously characterized (TAT, TAX19, T2αH, TBT, T7βH and TOT) and described in this study (Τ9αH-750C, T7AT and T1βH). TAX19 is used to generate known 13- O -acetylated products, including taxusin ( 6 ) and baccatin VI ( 11-Bz ), for structural analysis. Diamond indicates the structure is supported by NMR. d , EICs of expected products when the pathway to 6O4A is expressed with TOT, T7AT or both in N. benthamiana . In the absence of T7AT, no notable 6O4A depletion or product formation by TOT is observed. e , MS/MS fragmentation patterns of heterologously produced baccatin VI ( 11-Bz ) in N. benthamiana compared with that of 11-Bz standard. MS/MS fragmentations were generated using [M+Na] + ( m / z = 737.2788) as the precursor ion and fragmented with a collision energy of 30 eV.
Techniques Used: Tandem Mass Spectroscopy, Produced, Generated
Figure Legend Snippet: Two 2-ODDs, T1βH-184 and T1βH-686, were expressed in N. benthamiana with four different background conditions: a , Feeding taxusin. b , Feeding taxusin and co-expressing T2αΗ, ΤΒΤ, Τ7βΗ, and Τ7Αc. c , Co-expressing full biosynthetic pathway to 7O5A, i.e. tHMGR, GGPPS, TDS, FOTO, T5αH, TAT, T10βH, DBAT, T13αΗ, T2αΗ, ΤΒΤ, Τ7βΗ, Τ7ΑΤ, ΤΟΤ. d , Co-expressing full biosynthetic pathway to 7O6A, i.e. 7O5A pathway and TAX19. EIC of mono-oxidized products on both C-2α- O -acetyl and -benzoyl precursors are shown as well as their potential structures. Among all products, 1β-hydroxytaxusin ( 6-O1 ) and 15-hydroxy-11(15→1) abeo -taxusin ( 6-O2 ) are confirmed by NMR (Supplementary Tables – ) while baccatin VI ( 11-Bz ) is confirmed by comparing to chemical standard (Fig. ). The observed product diversity (formation of multiple peaks) is likely to arise from the dual-function of T1βH and TOT: T1βH performs both 1β-hydroxylation and rearrangement to 11(15→1) abeo- taxane, and TOT generates both epoxide and oxetane products. Notably, C-2α- Ο -benzoylated products mostly show as a single dominant peak. This suggests that the T1βΗ 1β-hydroxylation activity is selective toward C-2α- O -benzoylated/oxetane intermediates. e , Proposed mechanism of T1βH. Formation of the two characterized products 1β-hydroxytaxusin ( 6-O1 ) and 15-hydroxy-11(15→1) abeo -taxusin ( 6-O2 ) from taxusin ( 6 ) by T1βH-184 can be explained by the different fates of the C-1 radical after the first proton abstraction: direct hydroxyl radical rebound from the enzyme would yield 1β-hydroxytaxusin ( 6-O1 ) while radical rearrangement forming C-1/11 bond followed by ring opening and hydroxyl radical rebound would give 15-hydroxy-11(15→1) abeo -taxusin ( 6-O2 ). The rearrangement route is likely to lead to many non-classical abeo- taxanes, like brevifoliol, while the 1β-hydroxylation leads to classical taxanes like baccatin VI ( 16 ).
Techniques Used: Expressing, Activity Assay
Figure Legend Snippet: a , Simplified representation of biosynthetic transformations (acetylation and oxidation) from taxadiene ( 1 ) to baccatin III ( 16 ). b , Proposed biosynthetic pathway from 10-Bz to Taxol ( 18 ). c , EICs of intermediates when the indicated sets of genes were expressed in N. benthamiana leaves. d , MS/MS of heterologously produced 16 compared with that of 16 standard. e , Heat map showing ranks of PCL candidates in Taxol gene modules. f , EICs of 16 and 17 from feeding 16 to N. benthamiana leaves expressing PAM, PCL and BAPT or from expressing the complete gene set. g , Ranks of new Taxol biosynthetic genes discovered in this paper by PCC to TDS using either bulk ( n = 79 samples) or mpXsn ( n = 17,143 cells across 3 experiments) data. Orange indicates anticipated discovery; pink indicates unexpected discovery. h , Heat map showing ranks of updated Taxol biosynthetic genes in the modules. i , Baccatin III ( 16 ) yields in μg per g dried weight (DW), quantified with standards , of our 17-gene pathway with each single-gene dropout tested in N. benthamiana . Yields from replicating published gene sets , and from T. media needles are shown for comparison. Data are mean ± s.d., n = 3 biological replicates (Supplementary Data ). j , EIC showing the proposed taxadien-5α,13α-diol produced by T13αH and facilitated by FoTO1 (Extended Data Fig. ). Over-oxidized derivative and TAX19-acetylated product are confirmed by NMR (diamond). k , Phylogenetic tree of Taxus P450s. See Extended Data Fig. . l , Single-cell expression of T5αΗ and T13αH. m , Taxol biosynthesis (blue shading) and the reconstituted 13α-acetoxy taxane biosynthesis. Structures assigned on the basis of high-resolution mass spectrometry (HRMS) (HRMS-predicted chemical formula), NMR (NMR analysis followed by purification) and/or HRMS/MS (MS/MS spectra comparison with authentic standards). A detailed biosynthetic pathway is shown in Extended Data Fig. .
Techniques Used: Tandem Mass Spectroscopy, Produced, Expressing, Comparison, Mass Spectrometry, Purification
Figure Legend Snippet: In this work, we demonstrated the complete transformation from taxadiene to 3’- N -debenzoyl-2’-deoxypaclitaxel, which is proposed to be two steps away to Taxol, in N. benthamiana . While T2’αΗ has been previously reported , , we were unable to reconstitute its activity. The first oxidation of taxadiene can be conducted by either T5αΗ or T13αH, under the modulation by FoTO1. Branching of the Taxol pathway occurs at multiple enzymatic steps, including previously characterized T14βH , and more recently reported TBT , T7AT, TOT – , and T1βH-184, leading to other taxanes (shown in the last panel). The structural differences of other taxanes to Taxol are highlighted in brown. Furthermore, TAX19 allows the reconstitution of branching pathway to 13α-acetoxy taxanes including taxusin ( 6 ), baccatin IV, baccatin VI ( 11-Bz ), and 9-dihydro-13-acetylbaccatin III (9DHAB, ) that can be confirmed with chemical standards (Fig. , Extended Data Figs. and ). However, the potential roles of these 13α-acetoxy taxanes as alternative intermediates toward baccatin III remain to be explored. The prevalence of these 13α-acetoxy taxanes in Taxus plants suggests it is difficult to rule out that the natural biosynthetic pathway might proceed through 13α-acetoxy intermediates. However, we were unable to identify a corresponding C-13α- O -deacetylase (question mark from to 16 ), which prevented us from accessing baccatin III ( 16 ) via this putative, alternative route. Similarly, 10-deacetylbaccatin III, an abundant taxane in most Taxus species, might be an alternative biosynthetic intermediate with DBAT catalysing a late-stage acetylation (question mark from to 10-deacetylbaccatin III) . Full enzyme names are provided in Supplementary Table .
Techniques Used: Transformation Assay, Activity Assay, Histone Deacetylase Assay
![a , Conversion of baccatin VI ( 11-Bz ) to 9-dihydro-13α-acetylbaccatin III (9DHAB, 13 ) by T7dA and T9dA in N. benthamiana leaves. T7dA and T9dA were heterologously expressed in N. benthamiana via Agrobacterium- mediated transient expression and baccatin VI ( 11-Bz ) 20 μM was fed to the leaves three days after infiltration. b , Reconstitution of 9DHAB ( 13 ) biosynthetic pathway in N. benthamiana . EICs of leaves expressing the reconstituted pathway compared to the 9DHAB standard are shown. MS/MS fragmentations were generated using [M+Na] + (m/z = 653.2576) as the precursor ion and fragmented with a collision energy of 30 eV. Regions between m/z 100 and 800 are shown.](https://pub-med-central-images-cdn.bioz.com/pub_med_central_ids_ending_with_0809/pmc12240809/pmc12240809__41586_2025_9090_Fig11_ESM.jpg "a , Conversion of baccatin VI ( 11-Bz ) to 9-dihydro-13α-acetylbaccatin III (9DHAB, ...")
Figure Legend Snippet: a , Conversion of baccatin VI ( 11-Bz ) to 9-dihydro-13α-acetylbaccatin III (9DHAB, 13 ) by T7dA and T9dA in N. benthamiana leaves. T7dA and T9dA were heterologously expressed in N. benthamiana via Agrobacterium- mediated transient expression and baccatin VI ( 11-Bz ) 20 μM was fed to the leaves three days after infiltration. b , Reconstitution of 9DHAB ( 13 ) biosynthetic pathway in N. benthamiana . EICs of leaves expressing the reconstituted pathway compared to the 9DHAB standard are shown. MS/MS fragmentations were generated using [M+Na] + (m/z = 653.2576) as the precursor ion and fragmented with a collision energy of 30 eV. Regions between m/z 100 and 800 are shown.
Techniques Used: Expressing, Tandem Mass Spectroscopy, Generated
![a , Untargeted analysis shows baccatin III ( 16 ) as a major product in the final step of pathway. Linear volcano plot comparing N. benthamiana leaves expressing the full baccatin III ( 16 ) pathway and full pathway without the penultimate enzyme T7dA (ΔT7dA). Metabolomic features with putative taxane masses are shown as dots whose sizes indicate EIC integrated area. P-values calculated by two-sided t-test with a Bonferroni correction for multiple hypothesis testing. The full baccatin III ( 16 ) pathway include: tHMGR, GGPPS, TDS, FoTO1, T5αΗ, ΤΑΤ, T10βH, DBAT, T13αH, T9αΗ-750C, T2αH, TBT, T7βH, T7AΤ, TOT, T1βH-686, T9dA, T7dA, and T9ox. b , 1 H-NMR spectra of partially purified baccatin III ( 16 ) from N. benthamiana and baccatin III ( 16 ) standard (CDCl 3 , 500 ΜΗz, 298 K). The spectra of our partially purified baccatin III ( 16 ) align with the standard, exhibiting all characteristic peaks (labelled with carbon number) as well as the H-20 coupling constant ( J = 8.3 Hz) of the oxetane. The full baccatin III ( 16 ) pathway excluding T5αH was used to infiltrate 53 N. benthamiana plants [30.70 g DW] to yield baccatin III ( 16 ), whose yield (~270 μg) is derived from the total yield (1.33 mg) with an estimated 20% purity. c , T9αH-725A cannot complement T9αΗ-750C for baccatin III ( 16 ) production. Representative EIC of N. benthamiana leaves expressing our full baccatin III pathway gene set, compared to full gene set without TDS (ΔTDS) or an exchange of our T9αH-750C for the recently reported T9αH-725A – . Bar graph of integrated EICs for baccatin III ( 16 ) are shown. T9αH-725A pathway yields negligible baccatin III, statistically indistinguishable to a ΔTDS negative control. This would be expected from our finding that T9αH-725A appears to require a 13α- O -acetylation (Fig. ) that is absent from our baccatin III ( 16 ) pathway and from Taxol. Data are shown as the mean, n = 3 biological replicates. Significance indicates results of an ordinary one-way ANOVA comparison to the full pathway (**** P = 5.63 × 10 − 6 ). d , Variations in baccatin III ( 16 ) production. Bar graph showing baccatin III ( 16 ) yields from N. benthamiana leaves expressing the full 17-gene pathway from different plants, calculated based on a baccatin III standard curve. Each sample (dot) was taken from the 7th or 8th leaf counted from the bottom from separate plants under the same experimental conditions. The yields range from 1.7 ~ 31.5 μg/g DW, comparable to those reported for the twig and leaf samples from T. chinensis, T. cupsidata , and T. media . Furthermore, our isolated yield (~8.7 μg/g DW) aligns well with the calculated yield. Data are shown as the mean ± standard deviation, n = 6.](https://pub-med-central-images-cdn.bioz.com/pub_med_central_ids_ending_with_0809/pmc12240809/pmc12240809__41586_2025_9090_Fig12_ESM.jpg "a , Untargeted analysis shows baccatin III ( 16 ) as a major product ...")
Figure Legend Snippet: a , Untargeted analysis shows baccatin III ( 16 ) as a major product in the final step of pathway. Linear volcano plot comparing N. benthamiana leaves expressing the full baccatin III ( 16 ) pathway and full pathway without the penultimate enzyme T7dA (ΔT7dA). Metabolomic features with putative taxane masses are shown as dots whose sizes indicate EIC integrated area. P-values calculated by two-sided t-test with a Bonferroni correction for multiple hypothesis testing. The full baccatin III ( 16 ) pathway include: tHMGR, GGPPS, TDS, FoTO1, T5αΗ, ΤΑΤ, T10βH, DBAT, T13αH, T9αΗ-750C, T2αH, TBT, T7βH, T7AΤ, TOT, T1βH-686, T9dA, T7dA, and T9ox. b , 1 H-NMR spectra of partially purified baccatin III ( 16 ) from N. benthamiana and baccatin III ( 16 ) standard (CDCl 3 , 500 ΜΗz, 298 K). The spectra of our partially purified baccatin III ( 16 ) align with the standard, exhibiting all characteristic peaks (labelled with carbon number) as well as the H-20 coupling constant ( J = 8.3 Hz) of the oxetane. The full baccatin III ( 16 ) pathway excluding T5αH was used to infiltrate 53 N. benthamiana plants [30.70 g DW] to yield baccatin III ( 16 ), whose yield (~270 μg) is derived from the total yield (1.33 mg) with an estimated 20% purity. c , T9αH-725A cannot complement T9αΗ-750C for baccatin III ( 16 ) production. Representative EIC of N. benthamiana leaves expressing our full baccatin III pathway gene set, compared to full gene set without TDS (ΔTDS) or an exchange of our T9αH-750C for the recently reported T9αH-725A – . Bar graph of integrated EICs for baccatin III ( 16 ) are shown. T9αH-725A pathway yields negligible baccatin III, statistically indistinguishable to a ΔTDS negative control. This would be expected from our finding that T9αH-725A appears to require a 13α- O -acetylation (Fig. ) that is absent from our baccatin III ( 16 ) pathway and from Taxol. Data are shown as the mean, n = 3 biological replicates. Significance indicates results of an ordinary one-way ANOVA comparison to the full pathway (**** P = 5.63 × 10 − 6 ). d , Variations in baccatin III ( 16 ) production. Bar graph showing baccatin III ( 16 ) yields from N. benthamiana leaves expressing the full 17-gene pathway from different plants, calculated based on a baccatin III standard curve. Each sample (dot) was taken from the 7th or 8th leaf counted from the bottom from separate plants under the same experimental conditions. The yields range from 1.7 ~ 31.5 μg/g DW, comparable to those reported for the twig and leaf samples from T. chinensis, T. cupsidata , and T. media . Furthermore, our isolated yield (~8.7 μg/g DW) aligns well with the calculated yield. Data are shown as the mean ± standard deviation, n = 6.
Techniques Used: Expressing, Metabolomic, Purification, Derivative Assay, Negative Control, Comparison, Isolation, Standard Deviation
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