cas 102281-45-8, D-4-AMINOPHENYLALANINE | Articles data ｜lookchem

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102281-45-8

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Deracemization and stereoinversion to aromatic d-amino acid derivatives with ancestral l-amino acid oxidase
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.
Nakano, Shogo,Minamino, Yuki,Hasebe, Fumihito,Ito, Sohei
p. 10152 - 10158
(2019)
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Reconstruction of Hyper-Thermostable Ancestral L-Amino Acid Oxidase to Perform Deracemization to D-Amino Acids
L-amino acid oxidases (LAAOs) with broad substrate specificity can be used in the deracemization of D,L-amino acids (D,L-AAs) to their D-enantiomers. Hyper-thermostable LAAO (HTAncLAAO) was designed through a combination of manual sequence data mining and ancestral sequence reconstruction. Soluble expression of HTAncLAAO (>50 mg/L) can be achieved using an E. coli system. HTAncLAAO, which recognizes seven L-AAs as substrates, exhibits extremely high thermal stability and long-term stability; the t1/2 value was 95 °C and 99 % ee, D-enantiomer). These results suggest that HTAncLAAO is an excellent biocatalyst to perform this deracemization.
Ishida, Chiharu,Miyata, Ryo,Hasebe, Fumihito,Miyata, Azusa,Kumazawa, Shigenori,Ito, Sohei,Nakano, Shogo
p. 5228 - 5235
(2021/11/05)

Process Of Making Optically Pure Melphalan
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.
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Page/Page column 4

(2009/10/01)

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Chemical Properties

Appearance/Colour :white powder
Melting Point: 268-270 °C(lit.)
Boiling Point: 383.5 °C at 760 mmHg
Flash Point:185.8 °C
Density: 1.289 g/cm³
Solubility:H2O: 20 mg/mL, soluble
Storage Temp.:2-8°C
Vapor Pressure: 1.44E-06mmHg at 25°C
Refractive Index: 1.63
PKA: 2.14±0.10(Predicted)
PSA: 89.34000
LogP: 1.50470

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