102281-45-8Relevant articles and documents
Deracemization and stereoinversion to aromatic d-amino acid derivatives with ancestral l-amino acid oxidase
Nakano, Shogo,Minamino, Yuki,Hasebe, Fumihito,Ito, Sohei
, p. 10152 - 10158 (2019)
Enantiomerically pure amino acid derivatives could be foundational compounds for peptide drugs. Deracemization of racemates to l-amino acid derivatives can be achieved through the reaction of evolved d-amino acid oxidase and chemical reductants, whereas deracemization to d-amino acid derivatives has not progressed due to the difficulty associated with the heterologous expression of l-amino acid oxidase (LAAO). In this study, we succeeded in developing an ancestral LAAO (AncLAAO) bearing broad substrate selectivity (13 l-amino acids) and high productivity through an Escherichia coli expression system (50.7 mg/L). AncLAAO can be applied to perform deracemization to d-amino acids in a similar way to deracemization to l-amino acids. In fact, full conversion (>99% ee, d-form) could be achieved for 16 racemates, including nine d,l-Phe derivatives, six d,l-Trp derivatives, and a d,l-phenylglycine. Taken together, we believe that AncLAAO could be a key enzyme to obtain optically pure d-amino acid derivatives in the future.
Process Of Making Optically Pure Melphalan
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Page/Page column 4, (2009/10/01)
This invention provides a process of making 4-(bis-(2-hydroxyethyl)amino)-L-phenylalanine of the formula by hydroxyethylation, in a regioselective manner, of the aromatic amino group rather than the glycinic amino group.