Structure revision and absolute configuration of malhamensilipin A from the freshwater chrysophyte Poterioochromonas malhamensis.

Journal of Natural Products
Alban PereiraW H Gerwick

Abstract

Malhamensilipin A (2), a bioactive chlorosulfolipid initially reported in 1994 from the freshwater alga Poterioochromonas malhamensis, was reinvestigated for its structural and stereochemical features. HRESIMS data revealed that 2 possesses two sulfate groups rather than the one originally reported. A combination of J-based configurational and Mosher's analyses led us to assign its absolute configuration as 11R, 12S, 13S, 14R, 15S, and 16S. Finally, comparison of (1)H and (13)C NMR chemical shifts with synthetic standards confirmed that malhamensilipin A (2) possesses a terminal double bond of E configuration.

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Citations

Aug 22, 2013·Progress in Nuclear Magnetic Resonance Spectroscopy·Teodor Parella, Juan Félix Espinosa
Feb 10, 2010·Journal of the American Chemical Society·D Karl BedkeChristopher D Vanderwal
Feb 19, 2016·Organic Letters·Alexander R WhiteChristopher D Vanderwal
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Nov 28, 2015·Angewandte Chemie·Adrian M BaileyErick M Carreira
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Aug 10, 2013·Angewandte Chemie·Won-Jin ChungChristopher D Vanderwal
May 8, 2021·The Journal of Physical Chemistry Letters·Junyeol LeeRakwoo Chang
May 6, 2010·The Journal of Organic Chemistry·Takehiko YoshimitsuTetsuaki Tanaka
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Feb 4, 2011·Organic Letters·Takehiko YoshimitsuTetsuaki Tanaka
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Jun 28, 2019·Journal of the American Chemical Society·Philipp Sondermann, Erick M Carreira

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