Isolation, Total Synthesis, and Absolute Configuration
Determination of Renoprotective Dimeric N‑Acetyldopamine–Adenine
Hybrids from the Insect Aspongopus chinensis
Posted on 2020-06-11 - 18:35
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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Ding, Wei-Yi; Yan, Yong-Ming; Meng, Xiao-Hui; Nafie, Laurence A.; Xu, Te; Dukor, Rina K.; et al. (2020). Isolation, Total Synthesis, and Absolute Configuration
Determination of Renoprotective Dimeric N‑Acetyldopamine–Adenine
Hybrids from the Insect Aspongopus chinensis. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.0c01593
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AUTHORS (8)
WD
Wei-Yi Ding
YY
Yong-Ming Yan
XM
Xiao-Hui Meng
LN
Laurence A. Nafie
TX
Te Xu
RD
Rina K. Dukor
HQ
Hong-Bo Qin
YC
Yong-Xian Cheng
KEYWORDS
adductacetyldopamineRenal fibrosis inhibitionHybridstereoisomercomputationdichroism calculationssynthesisconfigurationCompounds 1Absolute Configuration Determination14- stepIsolationDimericChiral separationisomersAcetyldopaminevibrationaladenineTotal SynthesisRenoprotectiveracemateTGF -β1-induced rat kidney epithelial cellsInsect Aspongopus chinensis Aspongdopaminesinsect Aspongopus chinensis