2. Academic Validation
  3. Isolation, Total Synthesis, and Absolute Configuration Determination of Renoprotective Dimeric N-Acetyldopamine-Adenine Hybrids from the Insect Aspongopus chinensis

Isolation, Total Synthesis, and Absolute Configuration Determination of Renoprotective Dimeric N-Acetyldopamine-Adenine Hybrids from the Insect Aspongopus chinensis

  • Org Lett. 2020 Aug 7;22(15):5726-5730. doi: 10.1021/acs.orglett.0c01593.
Wei-Yi Ding 1,  Yong-Ming Yan 2,  Xiao-Hui Meng 2,  Laurence A Nafie 3,  Te Xu 2,  Rina K Dukor 4,  Hong-Bo Qin 1,  Yong-Xian Cheng 2
Affiliations

Affiliations

  • 1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P.R. China.
  • 2 School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, P.R. China.
  • 3 Department of Chemistry, Syracuse University, Syracuse, New York 13244-4100, United States.
  • 4 BioTools, Inc., 17546 Beeline Highway, Jupiter, Florida 33458, United States.
PMID: 32525688 DOI: 10.1021/acs.orglett.0c01593
Abstract

Aspongdopamines A and B (1 and 2), unusual adducts composed of N-acetyldopamine and adenine were isolated from the insect Aspongopus chinensis. Compounds 1 and 2 are positional isomers both isolated as racemates. Chiral separation assisted by 14-step total synthesis and computation including vibrational circular dichroism calculations allowed us to unambiguously assign the absolute configurations of eight stereoisomers. Renal fibrosis inhibition of the stereoisomers was evaluated in TGF-β1-induced rat kidney epithelial cells.

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