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Rapid and column-free syntheses of acyl fluorides and peptides using ex situ generated thionyl fluoride.

ABSTRACT: Thionyl fluoride (SOF₂) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for the ex situ generation of SOF₂ and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55-98% isolated yields under mild conditions and short reaction times. We further demonstrate its aptitude in amino acid couplings, with a one-pot, column-free strategy that affords the corresponding dipeptides in 65-97% isolated yields with minimal to no epimerization. The broad scope allows for a wide range of protecting groups and both natural and unnatural amino acids. Finally, we demonstrated that this new method can be used in sequential liquid phase peptide synthesis (LPPS) to afford tri-, tetra-, penta-, and decapeptides in 14-88% yields without the need for column chromatography. We also demonstrated that this new method is amenable to solid phase peptide synthesis (SPPS), affording di- and pentapeptides in 80-98% yields.

SUBMITTER: Lee C

PROVIDER: S-EPMC8694322 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:BackgroundOil spills can cause severe damage within a marine ecosystem. Following a spill, the soluble fraction of polycyclic aromatic hydrocarbons is rapidly released into the water column. These remain dissolved in seawater over an extended period of time, even should the insoluble fraction be removed. The vertical distribution of the aromatic hydrocarbon component and how these become transferred is poorly understood in brackish waters. This study examines the vertical distribution of polycyclic aromatic hydrocarbons having been released from a controlled film of spilled oil onto the surface of brackish water.MethodsThe study was undertaken under controlled conditions so as to minimize the variability of environmental factors such as temperature and hydrodynamics. The distribution of polycyclic aromatic hydrocarbons was measured in the dissolved and suspended phases throughout the 1 m water column with different intensity of water sampling: 1, 2, 4, 7, 72, 120, 336, 504 and 984 h.ResultsThe total concentration of polycyclic aromatic hydrocarbons ranged from 19.01 to 214.85 ng L-1 in the dissolved phase and from 5.14 to 63.92 ng L-1 in the suspended phase. These hydrocarbons were released immediately following a controlled spill attaining 214.9 ng L-1 in the dissolved phase and 54.4 ng L-1 in the suspended phase near the cylinder bottom after 1-2 h. The 2-3 ring polycyclic aromatic hydrocarbons dominated in the dissolved phase (60-80%), whereas the greater amount of 4-6 ring polycyclic aromatic hydrocarbons (55-90%) occurred in the suspended phase. A relatively low negative correlation (rS = -0.41) was determined between the concentration of phenanthrene and suspended matter, whereas a high negative correlation (r = - 0.79) was found between the concentration of pyrene and suspended matter. Despite the differences in the relationships between the concentration ratio and amount of suspended matter the obtained regressions allow roughly to predict the concentration of polycyclic aromatic hydrocarbons.

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Rapid and column-free syntheses of acyl fluorides and peptides using ex situ generated thionyl fluoride.

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