![(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid structure](https://static.chemtradehub.com/structs/630/63039-48-5-b66d.webp "(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid structure")
(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid
CAS Number:
63039-48-5
Molecular Formula:
C10H15NO4
Structurally diverse diketopiperazine alkaloids from the marine-derived fungus Aspergillus versicolor SCSIO 41016
Literature Information
Publication Date
2019-01-30
DOI
10.1039/C8QO01147H
Impact Factor
5.281
Authors
Huaming Tao, Xiuping Lin, Bin Yang, Xuefeng Zhou
View Original
Abstract
Ten new diketopiperazine alkaloids (DAs, 1–10) along with two known congeners (11–12) were characterized from the marine sponge-derived fungus Aspergillus versicolor SCSIO 41016. Their structures including absolute configurations were determined by spectroscopic analyses, quantum chemical calculations, and X-ray diffraction analysis. Pyranamides A–D (1–4) were obtained as rare 1-oxa-8,10-diazaspiro[5.5]undecane containing diketopiperazine alkaloids, while secopyranamide C (5) was obtained as a tetrahydropyran-ring cleavage derivative. Plausible biosynthetic pathways of 1–12 were postulated. Compounds 7 and 12 exhibited weak cytotoxic activities against ACHN, OS-RC-2, and 786-O cells.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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