282726-23-2Relevant articles and documents
A simple regiospecific strategy for labelling hydrogen atoms in α-amino acids
Pearce,Hammershoi,Harrowfield,Sargeson
, p. 2431 - 2432 (2000)
Simple methods for the regioselective introduction of deuterium labels at the α- and β-carbon atoms of leucine using a Co(III) imino acid complex are described which have a general applicability to the synthesis of a range of labelled amino acids.
Photochemical Deracemization at sp3-Hybridized Carbon Centers via a Reversible Hydrogen Atom Transfer
Bach, Thorsten,Breitenlechner, Stefan,Gro?kopf, Johannes,Plaza, Manuel,Seitz, Antonia,Storch, Golo
supporting information, p. 21241 - 21245 (2021/12/27)
A photochemical deracemization of 5-substituted 3-phenylimidazolidine-2,4-diones (hydantoins) is reported (27 examples, 69%-quant., 80–99% ee). The reaction is catalyzed by a chiral diarylketone which displays a two-point hydrogen bonding site. Mechanistic evidence (DFT calculations, radical clock experiments, H/D labeling) suggests the reaction to occur by selective hydrogen atom transfer (HAT). Upon hydrogen binding, one substrate enantiomer displays the hydrogen atom at the stereogenic center to the photoexcited catalyst allowing for a HAT from the substrate and eventually for its conversion into the product enantiomer. The product enantiomer is not processed by the catalyst and is thus enriched in the photostationary state.
Catalytic Stereoinversion of L -Alanine to Deuterated D -Alanine
Moozeh, Kimia,So, Soon Mog,Chin, Jik
, p. 9381 - 9385 (2015/08/06)
A combination of an achiral pyridoxal analogue and a chiral base has been developed for catalytic deuteration of L-alanine with inversion of stereochemistry to give deuterated D-alanine under mild conditions (neutral pD and 25°C) without the use of any pr
Measurement of biosynthesis and breakdown rates of biological molecules that are inaccessible or not easily accessible to direct sampling, non-invasively, by label incorporation into metabolic derivatives and catabolitic products
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Page 4, (2008/06/13)
Methods of determining rate of biosynthesis or breakdown of biological molecules from metabolic derivatives and catabolic products are disclosed herein. In particular, methods of measuring the rates of biosynthesis and breakdown of biological molecules inaccessible or not easily accessible to direct sampling by sampling metabolic derivatives and catabolic products in accessible biological samples are disclosed herein.
Simple and efficient preparation of (R)- and (S)-enantiomers of α-carbon deuterium-labelled α-amino acids
Mitulovi, Goran,Laemmerhofer, Michael,Maier,Lindner, Wolfgang
, p. 449 - 461 (2007/10/03)
A procedure for the synthesis of (R)- and (S)-enantiomers of α-carbon deuterium-labelled α-amino acids, exemplified for (R)- and (S)-[2-2H1]-Leu is described. Starting from the respective (S)- or (R)-enantiomer or from the racemic mixture of an α-amino acid the selective proton exchange at the α-carbon is carried out by racemization via a Schiff base in monodeuterated acetic acid as solvent which serves as deuterium source. After N-protection the racemic mixture is liquid chromatographically separated into the individual (R)- and (S)-enantiomers on preparative scale employing a chiral anion exchanger based on carbamoylated quinine as chiral selector. After deprotection the enantiomerically pure products can be obtained in good yields.
