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Activation of Fmoc-Val-OH with cyanuric fluoride (10 equiv) in the presence of pyridine (1 equiv) in DCM for 2 h under reflux. Filtration of the precipitate and removing of solvent gave Fmoc-Val-F quantilatively.
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84920296966
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Integration of Cα protons affords the same cis content. Due to signal overlap in some cases, the NH-pNA was chosen for all compounds to determine their cis/trans ratios.
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84920296964
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1H NMR was observed.
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84920296963
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The cis/trans ratios of all compounds were determined by the integration of the 2-C protons which for each of the cis and the trans form give separate singlet-signals at around 6.1 and 6.2 ppm, respectively.
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39
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84920296962
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note
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1H NMR spectrum in DMSO shows one predominant conformation. For certain protons such as the NH-pNA proton, traces of another conformation can be detected. However, due to a relative intensity of less than 3% with respect to the major conformation, an unambiguous assignment is impossible. It was yet detected by the CT coupled assay that very few percent of the trans form exist depending on temperature and solvent.
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