- Preparation of Deuterium Labeled Compounds by Pd/C-Al-D2O Facilitated Selective H-D Exchange Reactions
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The chemo/regioselective H-D exchange of amino acids and synthetic building blocks by an environmentally benign Pd/C-Al-D2O catalytic system is described. Due to the importance of isotope labeled compounds in medicinal chemistry and structural biology, no
- Kadish, Dora,Kokel, Anne,T?r?k, Béla
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supporting information
(2022/01/24)
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- Catalytic Stereoinversion of L -Alanine to Deuterated D -Alanine
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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
- Moozeh, Kimia,So, Soon Mog,Chin, Jik
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p. 9381 - 9385
(2015/08/06)
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- A stereoselective synthesis of α-deuterium-labelled (S)-α-amino acids
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An atom-efficient and stereoselective synthesis has been developed for the preparation of α-2H-labelled (S)-α-amino acids, starting from a novel chiral diketopi-perazine scaffold. Efficient mono-alkylation of the chiral template afforded the (S)-substituted adducts with the nature of the electrophile significantly effecting the stereochemical outcome. Subsequent alkylation was totally selective producing the 1, 4-cis adduct as the sole diastereoisomer. The deprotection was carried out using cerium ammonium nitrate followed by acid hydrolysis affording the enantipure α-amino acids. Springer-Verlag 2010.
- O'Reilly, Elaine,Balducci, Daniele,Paradisi, Francesca
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scheme or table
p. 849 - 858
(2010/11/05)
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- Synthesis of Nonproteinogenic (R)- or (S)-Amino Acids. - Analogues of Phenylalanine, Isotopically Labelled and Cyclic Amino Acids from tert-Butyl 2-(tert-Butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate (Boc-BMI)
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The enantiomerically pure glycine derivatives (R)- and (S)-Boc-BMI, commercially available on a kg scale, are used as starting materials (Scheme 1) for the preparation of (i) open-chain amino acids such as α-deuterio amino acids (4,5), β-arylalanines (2), aspartic acid derivatives (6, 7a, 8), or ω-halo amino acids (7b,c, 12, 13, 16, 17, 19, 22), (ii) of α-aminocycloalkanecarboxylic acids (9, 11), and (iii) of heterocyclic α-amino acids (14, 15, 18, 20) containing azetidine, pyrrolidine, piperidine or perhydroazepine rings.Inversion by deprotonation/protonation ordeuteration allows to prepare either enantiomer of an amino acid from the same Boc-BMI enantiomer (Scheme 5).Effects of additives such as the cyclic urea DMPU, lithium salts, or secondeary amines upon the reactivity of lithium enolates are discussed and, in part, exploited.
- Seebach, Dieter,Dziadulewicz, Edward,Behrendt, Linda,Cantoreggi, Sergio,Fitzi, Robert
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p. 1215 - 1232
(2007/10/02)
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- Solution-Phase Raman Studies of Alanyl Dipeptides and Various Isotopomers: A Reevaluation of the Amide III Vibrational Assignment
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Solution-phase Raman spectra of L-alanyl-L-alanine and five nitrogen and/or α-deuterated isotopomers are reported.Detailed vibrational assignments on this set of spectra have led to a somewhat different interpretation of the amide III vibrational region, as compared to literature assignments.The differences result from the fact that, in these deuterated samples, the nature of certain vibrations, and their interactions with other vibrations of similar energies, may be investigated with very high sensitivity.A discussion of the observed interaction of the amide III vibration and the methine deformation is presented, leading to an explanation for the geometric sensitivity of the band commonly referred to as the "amide III" mode.
- Oboodi, M. Reza,Alva, Carlos,Diem, Max
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p. 501 - 505
(2007/10/02)
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