Journal
ORGANIC LETTERS
Volume 24, Issue 51, Pages 9468-9472Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03922
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Funding
- Leidos Biomedical Research, Inc.
- Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research
- National Cancer Institute, National Institutes of Health [HHSN261200800001E]
- National Cancer Institutes Cancer Moonshot SM Progra
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A new dimeric alkaloid, Plakoramine A, was discovered from a marine sponge. It showed potent inhibition of ubiquitin ligase activities. The study also revealed a previously undescribed route to form this compound through photochemical conversion.
A new dimeric alkaloid plakoramine A [(+/-)-1] was identified from a marine sponge Plakortis sp. Chiral-phase HPLC separation of (+/-)-1 led to the purified enantiomers (+)-1 and (-)-1 which both potently inhibited CBL-B E3 ubiquitin ligase activities. The absolute configurations of the enantiomers were determined by quantum chemical calculations. Scrutinization of the purification conditions revealed a previously undescribed, nonenzymatic route to form (+/-)-1 via photochemical conversion of its naturally occurring monomeric counterpart, plakinidine B (2).
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