Azaserine, a New Tumor-inhibitory Substance. Isolation and Characterization<sup>1</sup>

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

doi:10.1021/ja01640a006

Cited by 34 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The first diazo-containing metabolites discovered were modified α-amino acids, and many were evaluated clincally. 412–418 The bioactivities of diazo-containing compounds are thought to arise from the reactivity of the diazo functional group. 411 For example, the mechanism of action of the diazo-containing natural product lomaiviticin A ( 4 ) has been elucidated, and accumulation of DNA double strand breaks requires the presence of its two diazo groups.…”

Section: N–n Bond Forming Enzymesmentioning

confidence: 99%

Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

et al. 2017

View full text Add to dashboard Cite

Natural products that contain functional groups with heteroatom-heteroatom linkages (X–X, where X = N, O, S, and P) are a small yet intriguing group of metabolites. The reactivity and diversity of these structural motifs has captured the interest of synthetic and biological chemists alike. Functional groups containing X–X bonds are found in all major classes of natural products and often impart significant biological activity. This review presents our current understanding of the biosynthetic logic and enzymatic chemistry involved in the construction of X–X bond containing functional groups within natural products. Elucidating and characterizing biosynthetic pathways that generate X–X bonds could both provide tools for biocatalysis and synthetic biology, as well as guide efforts to uncover new natural products containing these structural features.

show abstract

Section: N–n Bond Forming Enzymesmentioning

confidence: 99%

Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

et al. 2017

View full text Add to dashboard Cite

show abstract

“…It was isolated from Streptomyces fragilis and reported in 1954 as part of a screening programme for new antitumour and antibiotic agents. [19][20][21] Isolated as a pale yellow-green crystalline substance, 22 the structure was determined as O-diazoacetyl-(L)-serine 1 by a combination of UV and IR spectroscopy and classical degradation studies. 23 The compound is readily synthesised by selective diazotisation of O-glycyl-(L)-serine (Scheme 1), although the yield in the diazotisation step is low.…”

Section: Azaserinementioning

confidence: 99%

Natural products containing a diazo group

Nawrat

Moody

2011

Nat. Prod. Rep.

View full text Add to dashboard Cite

Although diazo compounds are probably best known for their involvement as versatile intermediates in modern synthetic organic chemistry, a small number of such compounds also occur naturally. Many of the early examples, such as azaserine, originally isolated in the 1950s, have antitumour properties and consist of modified α-amino acids. More recently, other more complex diazo compounds have been isolated from natural sources, and these include diazobenzoquinones, diazonaphthoquinones, such as the SF2415 and A80915 antibiotics, and the diazofluorene-based kinamycins and lomaiviticins. This report will cover the isolation, biosynthesis, biological activity and synthesis of natural products containing a diazo group.

show abstract

“…), was originally isolated (3,4) from the culture fluid of Streptomyces fragilis ( 5 ) and subsequently obtained by synthesis (6)(7)(8). It is very soluble in water and slightly soluble in methanol, ethanol, and acetone (1). 157" dec. (8).…”

Section: And Other Glutamine Antagonistsmentioning

confidence: 99%