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Streptavidin-Hosted Organocatalytic Aldol Addition.

ABSTRACT: In this report, the streptavidin-biotin technology was applied to enable organocatalytic aldol addition. By attaching pyrrolidine to the valeric motif of biotin and introducing it to streptavidin (Sav), a protein-based organocatalytic system was created, and the aldol addition of acetone with p-nitrobenzaldehyde was tested. The conversion of substrate to product can be as high as 93%. Although the observed enantioselectivity was only moderate (33:67 er), further protein engineering efforts can be included to improve the selectivity. These results have proven the concept that Sav can be used to host stereoselective aldol addition.

SUBMITTER: Santi N

PROVIDER: S-EPMC7287710 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Streptavidin-Hosted Organocatalytic Aldol Addition.

Santi Nicolò N Morrill Louis C LC Luk Louis Y P LYP

Molecules (Basel, Switzerland) 20200525 10

In this report, the streptavidin-biotin technology was applied to enable organocatalytic aldol addition. By attaching pyrrolidine to the valeric motif of biotin and introducing it to streptavidin (Sav), a protein-based organocatalytic system was created, and the aldol addition of acetone with <i>p</i>-nitrobenzaldehyde was tested. The conversion of substrate to product can be as high as 93%. Although the observed enantioselectivity was only moderate (33:67 er), further protein engineering effort ...[more]

PMID: 32466220

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