267235-31-4Relevant articles and documents
The preparation of three new partially deuterated hexadecanethiols for applications in surface chemistry
Sheepwash, Erin E.,Rowntree, Paul A.,Schwan, Adrian L.
, p. 391 - 398 (2008)
The synthesis of three partially deuterated hexadecanethiols has been achieved. Thiols CH3(CH2)7(CD2) 8SH, CD3(CD2)7(CH2) 8SH and CD3(CH2)15SH were targeted, as these compounds, after formation of self-assembled monolayers on Au(1 1 1) or Au nanoparticles, can provide mechanistic information pertaining to reactive atom migrations within the assembly. The syntheses of each of these compounds called upon Grignard coupling chemistry, which was activated by Li 2CuCl4. Applicable deuterium containing fragments were either commercially obtained or constructed from by way of an inexpensive and efficient ring opening, protection and dimerization of THF-d8. Sulfur incorporation was by thiolacetate substitution or addition reactions. The protocols presented possess general applicability in a number of syntheses requiring block-deuterated fattyalkyl sections. Copyright
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)
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.
An Efficient Synthesis of 3-Alkylpyridine Alkaloids Enables Their Biological Evaluation
Kaplan, Anna R.,Schrank, Cassandra L.,Wuest, William M.
supporting information, p. 2487 - 2490 (2021/04/21)
3-Alkylpyridine alkaloids (3-APAs) isolated from the arctic sponge Haliclona viscosa are a promising group of bioactive marine alkaloids. However, due to limited bioavailability, investigations of their bioactivity have been hampered. Additionally, synthesis of a common intermediate requires the use of protecting groups and harsh conditions. In this work, we developed a simple and concise two-step route to nine different natural and synthetic haliclocyclins. These compounds displayed modest antibiotic activity against several Gram-positive bacterial strains.
Unified Strategy for 1,5,9- and 1,5,7-Triols via Configuration-Encoded 1,5-Polyol Synthesis: Preparation and Coupling of C15-C25 and C26-C40 Fragments of Tetrafibricin
Friedrich, Ryan M.,Bell, Jay Q.,Garcia, Alfredo,Shen, Zican,Friestad, Gregory K.
, p. 13650 - 13669 (2018/11/23)
Diverse classes of natural products contain chiral 1,5,9- and 1,5,7-triol stereotriads, including the novel fibrinogen receptor antagonist tetrafibricin. Biological activities associated with compounds containing these motifs warrant targeted synthetic st
