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Spectroscopic Evidence for the Unusual Stereochemical Configuration of an Endosome‐Specific Lipid
Author(s) -
Tan HuiHui,
Makino Asami,
Sudesh Kumar,
Greimel Peter,
Kobayashi Toshihide
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106470
Subject(s) - enantiopure drug , enantiomer , chemistry , endosome , stereochemistry , nuclear magnetic resonance spectroscopy , camphor , reagent , organic chemistry , enantioselective synthesis , biochemistry , intracellular , catalysis
At a glance : The stereochemical configuration of the diglycerophosphate backbone of the endosome‐specific lipid bis(monoacylglycero)phosphate (BMP, see picture) was determined by 1 H NMR spectroscopy. Enantiomeric discrimination was facilitated by introduction of D ‐camphor ketals as chiral shift reagents, and enantiopure synthetic BMP analogues were prepared as reference materials. Natural BMP exhibited the unusual sn ‐1,1′ diglycerophosphate backbone.