38155-16-7Relevant academic research and scientific papers
Deprotonation of the peptide NH groups and diastereoselective hydrogenation of N-acetyl-α,β-dehydrodipeptides
Lisichkina,Ivanova,Peregudov,Belikov
, p. 738 - 739 (2007/10/03)
The peptide protons in N-acetyl-α,β-dehydrodipeptides (DHDP) dissociate in aqueous methanol in the presence of magnesium salts upon the addition of alkali, which favors the diastereoselectivities of their hydrogenation over Pd/C. By contrast, the N-H bond
Asymmetric hydrogenation of N-acetylhydrodipeptide complexes with Mg(II) and C(II) ions
Lisichkina, I. N.,Vinogradova, A. I.,Sukhorukova, N. B.,Tselyapina, E. V.,Saporovskaya, M. B.,Belikov, V. M.
, p. 569 - 571 (2007/10/02)
N-Ac-Δ-Phe-AA form labile complexes with Mg(II) ions.Potentiometric titration data show that the carboxyl group of the dehydropeptide in them scarcely participates in complexation, unlike the complexes with Ca(II) ions.The hydrogenation of these complexes
Efficient 1,4-Asymetric Induction Utilizing Electrostatic Interaction between Ligand and Substrate in the Asymmetric Hydrogenation of Didehydrodipeptides
Yamagishi, Takamichi,Ikeda, Satoru,Yatagai, Masanobu,Yamaguchi, Motowo,Hida, Mitsuhiko
, p. 1787 - 1790 (2007/10/02)
Electrostatic interaction between the amino group of the achiral 3-dimethylaminopropylidenebismethylenebis(diphenylphosphine) (1) and the carboxy group of the substrate enable an effective 1,4-asymmetric induction in the RhI-catalysed hydrogenation of didehydrodipeptides, to give (S,S)-or (R,R)-products selectively.The selectivity reached up to 94percent diastereoisomeric excess with acetyl didehydrodipeptides and 92percent with benzyloxycarbonyl substrates.
ASYMMETRIC HOMOGENOUS REDUCTION OF DEHYDROPEPTIDES
El-Baba, S.,Nuzillard, J. M.,Poulin, J. C.,Kagan, H. B.
, p. 3851 - 3862 (2007/10/02)
Monodehydropeptides with the dehydroaminoacid fragment in C-terminal or N-terminal position were synthetized as well as a family with the general formula Ac-ΔPhe-(Gly)n-Leu-OR (n = 0-2, R = H or Me).Asymmetric reduction of these compounds catalyzed by chiral rhodium complexes was investigated.The results were discussed in terms of double asymmetric induction.A method was developped to avoid the use of both enantiomers of the substrate or of the catalyst, it consists in the total reduction of a racemic dehydropeptide.The products distribution gives access to the two desired facial selectivities.
