A useful route to (R)- and (S)-tert-leucine

Allenmark, Stig; Lamm, Bo

doi:10.1002/1520-636x(2001)13:1<43::aid-chir9>3.0.co;2-g

Cited by 10 publications

(6 citation statements)

References 12 publications

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“…The crucial amino acids in this regard, L -tert-leucine, is extensively used for templates in asymmetric synthesis based on its oxazolidine moiety. In addition, L -tert-leucine itself is an ingredient of several pharmaceutical developmental products, such as anti-HIV protease inhibitors or tumour-fighting agents (12,13).…”

Section: Introductionmentioning

confidence: 99%

Biochemical and structural characterization of a highly active branched-chain amino acid aminotransferase from Pseudomonas sp. for efficient biosynthesis of chiral amino acids

Zheng

Cui

et al. 2019

Appl Microbiol Biotechnol

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Aminotransferases (ATs) are important biocatalysts for the synthesis of chiral amines because of their capability of introducing amino group into ketones or keto acids as well as their high enantioselectivity, high regioselectivity and no requirement of external addition of cofactor. Among all ATs, branched-chain amino acid aminotransferase (BCAT) can reversibly catalyse branched-chain amino acids (BCAAs), including L -valine, L -leucine, and L -isoleucine, with α-ketoglutaric acid to form the corresponding ketonic acids and L -glutamic acid. Alternatively, BCATs have been used for the biosynthesis of unnatural amino acids, such as L -tert-leucine. In the present study, the BCAT from Pseudomonas sp. (PsBCAT) was cloned and expressed in Escherichia coli for biochemical and structural analyses. The optimal reaction temperature and pH of PsBCAT were 40 ºC and 8.5, respectively.

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Section: Introductionmentioning

confidence: 99%

Biochemical and structural characterization of a highly active branched-chain amino acid aminotransferase from Pseudomonas sp. for efficient biosynthesis of chiral amino acids

Zheng

Cui

et al. 2019

Appl Microbiol Biotechnol

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“…Enantioselective chromatography or CEC employing chiral stationary phases (CSPs) are major techniques for the separation of enantiomers [15][16][17][18][19][20][21][22][23][24][25][40][41][42][43][44][45]. Polysaccharide based materials are the most prominent type of commercial CSPs due to their very broad spectrum of enantioselectivity towards different classes of chiral compounds [26].…”

Section: Introductionmentioning

confidence: 99%

“…Polysaccharide based materials are the most prominent type of commercial CSPs due to their very broad spectrum of enantioselectivity towards different classes of chiral compounds [26]. Other commercial CSPs are based on proteins [16,27], synthetic polymers [18], cyclodextrins [28], macrocyclic antibiotics [19,20], crown ethers [21,25], synthetic organic chiral molecules such as trans-1,2-diaminocyclohexane derivatives [23] and 4-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene (Whelk O1) [44], and quinine derivatives [3,9,15,24].…”

Section: Introductionmentioning

confidence: 99%

Zwitterionic codeine‐derived methacrylate monoliths for enantioselective capillary electrochromatography of chiral acids and chiral bases

et al. 2018

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Thiol-ene click reaction of N-acetyl-L-cysteine methyl ester to codeine, followed by reaction with allyl isocyanate and hydrolysis to the corresponding zwitterionic chiral selector and its subsequent bonding to the surface of a methacrylate monolith provided a new chiral capillary column for enantiomer separation of chiral acids and chiral bases. First, the epoxy groups of a poly(glycidyl methacrylate-co-ethylene dimethacrylate) monolith were converted into amine residues, followed by reaction with allylglycidyl ether. In this way, a spacer arm was bonded to the surface before coating and cross-linking poly(3-mercaptopropyl methylsiloxane) (PMPMS) via radical addition (thiol-ene click reaction) to the surface. In order to improve the performance of the monolithic chiral stationary phase, thio ether and residual thiol groups were oxidized to sulfonyl and sulphonate groups, respectively. This novel chiral stationary phase (CSP) was evaluated by capillary electrochromatography (CEC) using two chiral model compounds, namely N-3,5-dinitrobenzoyl-R,S-leucine (retained by anion-exchange mechanism) and mefloquine (by cation-exchange process). The ion-exchange retention mechanism on the CSP was characterized for these two counterionic model solutes by varying the mobile phase composition, including the nature of solvents, the concentration of counter-ions and co-ions, and the acid-to-base ratio. A series of chiral β-blockers and amino acid derivatives was used to further check the performance of the modified monolith under the optimal conditions. Several enantiomers were baseline resolved with reasonable peak efficiencies (up to 60,000 theoretical plates per meter for the second eluted enantiomer).

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“…[3,4] However,t he determination of absolute configurations is an ontrivial problem and can be ac hallenging task. [5] Thek nowledge of the absolute configuration is of great importance, e.g.,i nt he lock-and-key relationship [6] or structure-specific targeting in drug development. [7] Thec onfigurational standard of chiral molecules is dextrorotatory D-(+)-glyceraldehyde D-1 [8] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cryptochiral (R,R)‐2,3‐Dideuterooxirane as Stereochemical Reference Compound and Chemical Correlation with D‐(+)‐Glyceraldehyde

Trapp

Zawatzky

2016

Israel Journal of Chemistry

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Chirality plays a pivotal role in chemistry and biology, e.g., structure‐specific targeting in drug development or the lock‐and‐key theory of enzyme interactions. Determining absolute configurations of chiral molecules is essential to understanding such mechanisms and to developing chemical processes involving chiral compounds. In particular, this becomes obvious in the understanding of chemical reaction networks in the context of the origins of life. A stereochemical reference compound that can be correlated with sugars, amino acids, etc. is of great interest. Here, we present the synthesis of enantiopure (R,R)‐2,3‐dideuterooxirane, of which the absolute configuration has been unambiguously determined by foil‐induced Coulomb explosion imaging, and the correlation with the configuration of D‐(+)‐glyceraldehyde.

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A useful route to (R)- and (S)-tert-leucine

Abstract: Resolution of 1-(2-furyl)-2,2-dimethylpropylamine, an intermediate on a synthetic route to tert-leucine, followed by oxidation of the respective enantiomers, constitutes an interesting and useful strategy to (R)- and (S)-tert-leucine.

Cited by 10 publications

References 12 publications

Biochemical and structural characterization of a highly active branched-chain amino acid aminotransferase from Pseudomonas sp. for efficient biosynthesis of chiral amino acids

Biochemical and structural characterization of a highly active branched-chain amino acid aminotransferase from Pseudomonas sp. for efficient biosynthesis of chiral amino acids

Zwitterionic codeine‐derived methacrylate monoliths for enantioselective capillary electrochromatography of chiral acids and chiral bases

Synthesis of Cryptochiral (R,R)‐2,3‐Dideuterooxirane as Stereochemical Reference Compound and Chemical Correlation with D‐(+)‐Glyceraldehyde

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