943-80-6Relevant 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 (2019/10/19)
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.
Distinct metabolites for photoreactive l-phenylalanine derivatives in Klebsiella sp. CK6 isolated from rhizosphere of a wild dipterocarp sapling
Wang, Lei,Hisano, Wataru,Murai, Yuta,Sakurai, Munenori,Muto, Yasuyuki,Ikemoto, Haruka,Okamoto, Masashi,Murotani, Takashi,Isoda, Reika,Kim, Dongyeop,Sakihama, Yasuko,Sitepu, Irnayuli R.,Hashidoko, Yasuyuki,Hatanaka, Yasumaru,Hashimoto, Makoto
, p. 8393 - 8401 (2013/08/23)
Photoaffinity labeling is a reliable analytical method for biological functional analysis. Three major photophores-aryl azide, benzophenone and trifluoromethyldiazirine- are utilized in analysis. Photophore-bearing L-phenylalanine derivatives, which are used for biological functional analysis, were inoculated into a Klebsiella sp. isolated from the rhizosphere of a wild dipterocarp sapling in Central Kalimantan, Indonesia, under nitrogen-limiting conditions. The proportions of metabolites were quite distinct for each photophore. These results indicated that photophores affected substrate recognition in rhizobacterial metabolic pathways, and differential photoaffinity labeling could be achieved using different photophore-containing L-phenylalanine derivatives.
Photoswitching of the Enzymatic Activity of Semisynthetic Ribonuclease S' Bearing Phenylazophenylalanine at a Specific Site
Hamachi, Itaru,Hiraoki, Takashi,Yamada, Yasuhiro,Shinkai, Seiji
, p. 704 - 706 (2007/10/03)
Photoswitching of the enzymatic activity of ribonuclease S' was successfully carried out by site specific incorporation of phenylazophenylalanine into S-peptide skeleton by semisynthesis.
