Biocatalysis of a Paclitaxel Analogue: Conversion of Baccatin III to N-Debenzoyl-N-(2-furoyl)paclitaxel and Characterization of an Amino Phenylpropanoyl CoA Transferase

Biochemistry ◽  
2017 ◽  
Vol 56 (44) ◽  
pp. 5920-5930 ◽  
Author(s):  
Chelsea K. Thornburg ◽  
Tyler Walter ◽  
Kevin D. Walker
Keyword(s):  
2013 ◽  
Vol 98 (8) ◽  
pp. 3579-3589 ◽  
Author(s):  
Elena Volodina ◽  
Marc Schürmann ◽  
Nicole Lindenkamp ◽  
Alexander Steinbüchel

2002 ◽  
Vol 184 (1) ◽  
pp. 216-223 ◽  
Author(s):  
Markus Göbel ◽  
Kerstin Kassel-Cati ◽  
Eberhard Schmidt ◽  
Walter Reineke

ABSTRACT 3-Oxoadipate:succinyl-coenzyme A (CoA) transferase and 3-oxoadipyl-CoA thiolase carry out the ultimate steps in the conversion of benzoate and 3-chlorobenzoate to tricarboxylic acid cycle intermediates in bacteria utilizing the 3-oxoadipate pathway. This report describes the characterization of DNA fragments with the overall length of 5.9 kb from Pseudomonas sp. strain B13 that encode these enzymes. DNA sequence analysis revealed five open reading frames (ORFs) plus an incomplete one. ORF1, of unknown function, has a length of 414 bp. ORF2 (catI) encodes a polypeptide of 282 amino acids and starts at nucleotide 813. ORF3 (catJ) encodes a polypeptide of 260 amino acids and begins at nucleotide 1661. CatI and CatJ are the subunits of the 3-oxoadipate:succinyl-CoA transferase, whose activity was demonstrated when both genes were ligated into expression vector pET11a. ORF4, termed catF, codes for a protein of 401 amino acid residues with a predicted mass of 41,678 Da with 3-oxoadipyl-CoA thiolase activity. The last three ORFs seem to form an operon since they are oriented in the same direction and showed an overlapping of 1 bp between catI and catJ and of 4 bp between catJ and catF. Conserved functional groups important for the catalytic activity of CoA transferases and thiolases were identified in CatI, CatJ, and CatF. ORF5 (catD) encodes the 3-oxoadipate enol-lactone hydrolase. An incomplete ORF6 of 1,183 bp downstream of ORF5 and oriented in the opposite direction was found. The protein sequence deduced from ORF6 showed a putative AMP-binding domain signature.


2006 ◽  
Vol 72 (8) ◽  
pp. 5403-5413 ◽  
Author(s):  
Allyson M. MacLean ◽  
Gordon MacPherson ◽  
Punita Aneja ◽  
Turlough M. Finan

ABSTRACT Aromatic compounds represent an important source of energy for soil-dwelling organisms. The β-ketoadipate pathway is a key metabolic pathway involved in the catabolism of the aromatic compounds protocatechuate and catechol, and here we show through enzymatic analysis and mutant analysis that genes required for growth and catabolism of protocatechuate in the soil-dwelling bacterium Sinorhizobium meliloti are organized on the pSymB megaplasmid in two transcriptional units designated pcaDCHGB and pcaIJF. The pcaD promoter was mapped by primer extension, and expression from this promoter is demonstrated to be regulated by the LysR-type protein PcaQ. β-Ketoadipate succinyl-coenzyme A (CoA) transferase activity in S. meliloti was shown to be encoded by SMb20587 and SMb20588, and these genes have been renamed pcaI and pcaJ, respectively. These genes are organized in an operon with a putative β-ketoadipyl-CoA thiolase gene (pcaF), and expression of the pcaIJF operon is shown to be regulated by an IclR-type transcriptional regulator, SMb20586, which we have named pcaR. We show that pcaR transcription is negatively autoregulated and that PcaR is a positive regulator of pcaIJF expression and is required for growth of S. meliloti on protocatechuate as the carbon source. The characterization of the protocatechuate catabolic pathway in S. meliloti offers an opportunity for comparison with related species, including Agrobacterium tumefaciens. Differences observed between S. meliloti and A. tumefaciens pcaIJ offer the first evidence of pca genes that may have been acquired after speciation in these closely related species.


Genomics ◽  
2000 ◽  
Vol 68 (2) ◽  
pp. 144-151 ◽  
Author(s):  
Toshiyuki Fukao ◽  
Grant A. Mitchell ◽  
Xiang-Qian Song ◽  
Haruki Nakamura ◽  
Sacha Kassovska-Bratinova ◽  
...  

2020 ◽  
Vol 18 (12) ◽  
pp. 2219-2222 ◽  
Author(s):  
Fleurdeliz Maglangit ◽  
Saad Alrashdi ◽  
Justine Renault ◽  
Laurent Trembleau ◽  
Catherine Victoria ◽  
...  

More than 500 siderophores are known to date, but only three were identified to be aryl-containing hydroxamate siderophores, legonoxamines A and B from Streptomyces sp. MA37, and aryl ferrioxamine 2 from Micrococcus luteus KLE1011.


Author(s):  
Toshiyuki Fukao ◽  
Jörn Oliver Sass ◽  
Petri Kursula ◽  
Eva Thimm ◽  
Udo Wendel ◽  
...  

2012 ◽  
Vol 7 (9) ◽  
pp. 1934578X1200700
Author(s):  
Kalle Truus ◽  
Merike Vaher ◽  
Maria Borissova ◽  
Marju Robal ◽  
Tuuli Levandi ◽  
...  

The composition of varieties of Taxus growing in Estonia was analyzed by capillary electrophoresis with diode array detection (CE-DAD) for the separation of phenolic compounds, and by high performance liquid chromatography-mass spectrometry (HPLC-MS) for the determination of taxoids. The main purpose of this study was the chemotaxonomic differentiation of varieties of Taxus by using data from these analyses. Fingerprints scanned at 214 nm on the basis of CE separation at pH 9.3 were used to characterize seven varieties of yew. The contents of four key taxoids (10-deacetylbaccatin, baccatin III, cephalomannine and paclitaxel) in six Taxus varieties were comparatively determined by HPLC-MS. The set of electropherograms/chromatograms of the various Taxus extracts were subjected to principal component analysis (PCA), using the peak areas of 16 phenolic compounds and 14 taxoids as characteristics. The formation of distinct clusters in accordance with botanical classification proves the suitability of PCA for differentiating varieties of Taxus.


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