Appearance: white crystalline powder
Specific rotation[a]D20: -61±2° (c=1, AcOH)
Melting point: 133-135℃
N-Boc-L-proline; Boc-Pro-OH 15761-39-4 is a useful synthetic intermediate. It is used to synthesize Daclatasvir which inhibits the HCV protein NS5A.
N-Boc-L-proline is the proline derivative utilized in Boc SPPS. Proline is the only standard amino acid having a secondary amine. Proline does not produce a blue or purple color when reacted with ninhydrin. To test the completion of coupling to proline residues, the isatin test or one of the alternate tests should be used. Proline residues within peptides and proteins lack an amide proton and can not function as hydrogen-bond donors. The conformational rigidity of proline residues normally disrupts alpha helix or beta sheet structure in proteins, but often contributes to turn or loop structures. Unlike other amino acids, the free enthalpy difference between the cis and trans isomers of the N-Pro amide bond are small and both isomers exist in solution. Although the free enthalpy difference between cis and trans isomers is small the rotational barrier is quite high. The cis-trans interconversion os one of the limiting steps in protein folding.
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