324010-83-5Relevant academic research and scientific papers
Azidosphinganine enables metabolic labeling and detection of sphingolipidde novosynthesis
Fink, Julian,Schumacher, Fabian,Schlegel, Jan,Stenzel, Philipp,Wigger, Dominik,Sauer, Markus,Kleuser, Burkhard,Seibel, Jürgen
, p. 2203 - 2212 (2021/03/24)
Here were report the combination of biocompatible click chemistry of ω-azidosphinganine with fluorescence microscopy and mass spectrometry as a powerful tool to elaborate the sphingolipid metabolism. The azide probe was efficiently synthesized over 13 steps starting froml-serine in an overall yield of 20% and was used for live-cell fluorescence imaging of the endoplasmic reticulum in living cells by bioorthogonal click reaction with a DBCO-labeled fluorophore revealing that the incorporated analogue is mainly localized in the endoplasmic membrane like the endogenous species. A LC-MS(/MS)-based microsomalin vitroassay confirmed that ω-azidosphinganine mimics the natural species enabling the identification and analysis of metabolic breakdown products of sphinganine as a key starting intermediate in the complex sphingolipid biosynthetic pathways. Furthermore, the sphinganine-fluorophore conjugate after click reaction was enzymatically tolerated to form its dihydroceramide and ceramide metabolites. Thus, ω-azidosphinganine represents a useful biofunctional tool for metabolic investigations both byin vivofluorescence imaging of the sphingolipid subcellular localization in the ER and byin vitrohigh-resolution mass spectrometry analysis. This should reveal novel insights of the molecular mechanisms sphingolipids and their processing enzymes havee.g.in infection.
Enzyme-mediated preparation of optically active 1,2-diols bearing a long chain: Enantioselective hydrolysis of cyclic carbonates
Shimojo, Megumi,Matsumoto, Kazutsugu,Hatanaka, Minoru
, p. 9281 - 9288 (2007/10/03)
A new entry for the efficient preparation of optically active 1,2-diols having a long aliphatic chain via an enzymatic reaction is disclosed. PPL catalyzes the hydrolysis of a racemic five-membered cyclic carbonate, 4-(%benzyloxy)heptyl-1,3-dioxolan-2-one (2a), with high enantioselectivity to produce the optically active (R)-2a and (S)-9-benzyloxynonane-1,2-diol (3a) in excellent yields. The reaction is applicable to the substrates with a longer chain (10-benzyloxydecyl (3b) and 13-benzyloxytridecyl group (3c)). Optically pure (S)-(+)-8hydroxyhexadecanoic acid (1), a biologically active natural compound with a chiral long aliphatic part, is effectively synthesized starting from (R)-3-(7-benzyloxy)heptyl-2-oxirane (9), which is converted from both enantiomers of 3a. (C) 2000 Elsevier Science Ltd.
