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Cytochrome p450 taxadiene 5alpha-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis.
Meta-omic characterization of the marine invertebrate microbial consortium that produces the chemotherapeutic natural product ET-743.
This work focuses on the ET-743 (Yondelis) biosynthetic pathway, which is an approved anticancer agent obtained in low abundance from the tunicate Ecteinascidia turbinata and generated in suitable quantities for clinical use by a lengthy semisynthetic process.
Biosynthesis of Prenylated Alkaloids Derived from Tryptophan
The biosynthesis of prenylated indole alkaloids and related natural substances derived from tryptophan is reviewed and the groups selected based on their structural and biogenetic similarities are examined.
Taxol biosynthesis: Taxane 13α-hydroxylase is a cytochrome P450-dependent monooxygenase
- S. Jennewein, C. Rithner, Robert M. Williams, R. Croteau
- BiologyProceedings of the National Academy of Sciences…
- 13 November 2001
A PCR-based differential display-cloning approach yielded a family of related cytochrome P450 genes, one of which was assigned as a taxane 10β-hydroxylase by functional expression in yeast and validates this strategy for elucidating the oxygenation steps of taxane diterpenoid (taxoid) metabolism.
Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor.
- A. Bowers, N. West, J. Taunton, S. Schreiber, J. Bradner, Robert M. Williams
- Biology, ChemistryJournal of the American Chemical Society
- 19 July 2008
It is demonstrated that largazole is a pro-drug that is activated by removal of the octanoyl residue from the 3-hydroxy-7-mercaptohept-4-enoic acid moiety to generate the active metabolite 2, which is an extraordinarily potent Class I histone deacetylase inhibitor.
Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp.
- Yousong Ding, J. D. de Wet, D. Sherman
- Chemistry, BiologyJournal of the American Chemical Society
- 15 September 2010
The results establish the early steps for creation of the prenylated indole alkaloid structure and suggest a scheme for the biosynthesis of stephacidin and notoamide metabolites, providing the first genetic and biochemical insights for understanding the structural diversity of this important family of fungal alkaloids.
Differential effects of FR900482 and FK317 on apoptosis, IL-2 gene expression, and induction of vascular leak syndrome.
Enantiomeric natural products: occurrence and biogenesis.
- Jennifer M. Finefield, D. Sherman, M. Kreitman, Robert M. Williams
- ChemistryAngewandte Chemie
- 14 May 2012
In nature, chiral natural products are usually produced in optically pure form-however, occasionally both enantiomers are formed. These enantiomeric natural products can arise from a single species…
Synthesis of optically active α-amino acids
- Robert M. Williams
Asymmetric derivatization of glycine. Homologation of the beta-carbon. Electrophilic amination of enolates. Nucleophilic amination of alpha-substituted acids. Asymmetric Strecker syntheses.…
Comparative analysis of the biosynthetic systems for fungal bicyclo[2.2.2]diazaoctane indole alkaloids: the (+)/(-)-notoamide, paraherquamide and malbrancheamide pathways.
A comparative analysis of four natural product metabolic systems of a select group of bicyclo-diazaoctane indole alkaloids including (+)/(-)-notoamide, paraherquamide and malbrancheamide is reported, in which an enzyme for each step in the biosynthetic pathway is proposed based on deep annotation and on-going biochemical studies.