Azaserine, A New Tumour-Inhibitory Substance: Isolation and Characterization of Azaserine

Bartz, Quentin R.; Elder, Carole C.; Frohardt, Roger P.; Fusari, Salvatore A.; Haskell, Theodore H.; Johannessen, Doris W.; Ryder, Albert

doi:10.1038/173072b0

Cited by 73 publications

(25 citation statements)

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“…[1] They have been found in nature, examples of which include azaserine [2] and members of the kinamycin [3] and lomaiviticin [4] families of marine natural products. Depending upon their stability and coexisting functional groups, diazo-compounds can present a challenge with respect to their preparation and isolation.…”

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confidence: 99%

A Phosphine‐Mediated Conversion of Azides into Diazo Compounds

Myers

Raines

2009

Angew Chem Int Ed

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confidence: 99%

A Phosphine‐Mediated Conversion of Azides into Diazo Compounds

Myers

Raines

2009

Angew Chem Int Ed

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“…The biosynthetic origins of naturally-occurring diazo groups 22 has remained a mystery since the discovery of the first diazo-containing metabolite azaserine in 1954. 23 Feeding studies with the labeled aminobenzo[ b ]fluorene stealthin C resulted in incorporation into kinamycin, indicating that the two nitrogen atoms of the diazo group are introduced into the natural product scaffold in a stepwise manner. 9f A similar result was obtained from feeding experiments exploring the biosynthesis of azamerone, a natural product derived from a diazo-containing intermediate.…”

Section: Resultsmentioning

confidence: 99%

Discovery of the lomaiviticin biosynthetic gene cluster in Salinispora pacifica

et al. 2014

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The lomaiviticins are a family of cytotoxic marine natural products that have captured the attention of both synthetic and biological chemists due to their intricate molecular scaffolds and potent biological activities. Here we describe the identification of the gene cluster responsible for lomaiviticin biosynthesis in Salinispora pacifica strains DPJ-0016 and DPJ-0019 using a combination of molecular approaches and genome sequencing. The link between the lom gene cluster and lomaiviticin production was confirmed using bacterial genetics, and subsequent analysis and annotation of this cluster revealed the biosynthetic basis for the core polyketide scaffold. Additionally, we have used comparative genomics to identify candidate enzymes for several unusual tailoring events, including diazo formation and oxidative dimerization. These findings will allow further elucidation of the biosynthetic logic of lomaiviticin assembly and provide useful molecular tools for application in biocatalysis and synthetic biology.

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“…A related α-diazoester, azaserine ( 66 , Figure 23), is also naturally occurring and has antitumor and antibiotic properties. [194,195] The diazoketone group is set up for loss of dinitrogen (N 2 ) on attack by nucleophiles, so an engineered tRNA/tRNA synthetase pair for DON might be of use for selective reactivity.…”

Section: Amino Acids With Potentially Reactive Functional Groupsmentioning

confidence: 99%

Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds

2013

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Freestanding nonproteinogenic amino acids have long been recognized for their antimetabolite properties and tendency to be uncovered to reactive functionalities by the catalytic action of target enzymes. By installing them regiospecifically into biogenic peptides and proteins, it may be possible to usher a new era at the interface between small molecule and large molecule medicinal chemistry. Site‐selective protein functionalization offers uniquely attractive strategies for posttranslational modification of proteins. Last, but not least, many of the amino acids not selected by nature for protein incorporation offer rich architectural possibilities in the context of ribosomally derived polypeptides. This Review summarizes the biosynthetic routes to and metabolic logic for the major classes of the noncanonical amino acid building blocks that end up in both nonribosomal peptide frameworks and in hybrid nonribosomal peptide‐polyketide scaffolds.

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Azaserine, A New Tumour-Inhibitory Substance: Isolation and Characterization of Azaserine

Cited by 73 publications

References 0 publications

A Phosphine‐Mediated Conversion of Azides into Diazo Compounds

A Phosphine‐Mediated Conversion of Azides into Diazo Compounds

Discovery of the lomaiviticin biosynthetic gene cluster in Salinispora pacifica

Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds

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