68798-79-8Relevant articles and documents
In vitro evolution of an l-amino acid deaminase active on l-1-naphthylalanine
Melis, Roberta,Rosini, Elena,Pirillo, Valentina,Pollegioni, Loredano,Molla, Gianluca
, p. 5359 - 5367 (2018/10/23)
l-Amino acid deaminase from Proteus myxofaciens (PmaLAAD) is a promising biocatalyst for enantioselective biocatalysis that can be exploited to produce optically pure d-amino acids or α-keto acids. In this study, we improved the catalytic efficiency of PmaLAAD on l-1-naphthylalanine (l-1-Nal), a synthetic amino acid of biotechnological interest. Eight evolvable positions were identified by a molecular docking and evolutionary conservation analysis. These positions were subjected to site-saturation mutagenesis, producing smaller but smarter libraries of variants. The best variant (F318A/V412A/V438P PmaLAAD) possesses a ～5-fold lower Km (0.17 mM) and a ～7-fold higher catalytic efficiency (9.2 s-1 mM-1) on l-1-Nal than the wild-type enzyme. Molecular docking analysis suggests that the substitutions increase the active site volume, allowing better binding of the bulky l-1-Nal substrate. Bioconversion reactions showed that the F318A/V412A/V438P PmaLAAD variant outperforms the wild-type enzyme in the deracemization of d,l-1-Nal: the complete conversion of 0.6 mM of the l-enantiomer was achieved in about 15 min, which is ～7.5-fold faster than the wild-type enzyme. In addition, the F318A/V412A/V438P PmaLAAD is efficiently employed, together with the M213G d-amino acid oxidase variant, to produce 1-naphtylpyruvate from racemic d,l-1-Nal in one pot.
COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS
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Page/Page column 45-49; 61, (2010/12/31)
The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.
Asymmetric synthesis of (S)-2-amino-3-(1-naphthyl)propanoic acid via chiral nickel complex. Crystal structure, circular dichroism, 1H and 13C NMR spectra of the complex
Popkov, Alexander,Cisarova, Ivana,Sopkova, Jana,Jirman, Josef,Lycka, Antonin,Kochetkov, Konstantin A.
, p. 1397 - 1410 (2007/10/03)
The recently published environmentally friendly preparation of a glycine synthon 2 from regeneratable chiral auxiliary BPB ((S)-N-(2-benzoylphenyl)- N′-benzylprolinamide) was used for preparative asymmetric synthesis of the non-coded amino acid 3-(1-naphthyl)alanine (1). Full assignment of 1H and 13C NMR of both intermediate complex 3 and 1 and X-ray structure determination of complex 3 were made. Cotton effects observed in circular dichroism spectrum of complex 3 are consistent with published empirical rules.
