To combat SARS-CoV-2 and any unknown emerging pathogens in the future, the development of a rapid and effective method to generate high-affinity antibodies or antibody-like proteins is of critical importance. We here report a high-speed in vitro selection of multiple high-affinity antibody-like proteins against various targets including the SARS-CoV-2 spike protein. The sequences of monobodies against the SARS-CoV-2 spike protein were successfully procured within only four days. Furthermore, the obtained monobody efficiently captured SARS-CoV-2 particles from the nasal swab samples of patients and exhibited a high neutralizing activity against SARS-CoV-2 infection (IC50 = 0.5 nM). The high-speed in vitro selection of antibody-like proteins would be useful for the rapid development of a detection method and a neutralizing protein against a virus responsible for an ongoing, and possibly a future, pandemic.
In dichloromethane as a non-Lewis basic solvent, 1 -haloadamantane 1 underwent a cross-coupling reaction with Grignard reagents to give bridgehead-substituted products 3-16 in moderate yields. In this case the same kind of halogen in both 1 and a Grignard reagent was favored; if not, functional exchange (i.e., la to lc) occurred first. The reaction using 5-hexenylmagnesium bromide as a radical probe afforded uncyclized/cyclized coupling products in a 6/4 ratio. These facts suggested the significant participation of the single-electron-transfer process in these reactions. The present method could be extended to tert-butylation with some Grignard reagents. Interestingly, l,3-dichloro-3-methylbutane coupled with butylmagnesium chloride selectively at the tertiary position. For the above displacement reaction of 1, an organozinc was also found to be effective.
The 1‐adamantyl halides (I) undergo cross‐coupling reaction with the corresponding alkyl(aryl)magnesium compounds (II), (IV), or (VI) to produce the 1‐substituted adamantanes (III).
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