7376-90-1Relevant articles and documents
Hybrid catalysis of 8-quinolinecarboxaldehyde and br?nsted acid for efficient racemization of α-amino amides and its application in chemoenzymatic dynamic kinetic resolution
Kiyokawa, Mari,Nagato, Yuya,Ohmatsu, Kohsuke,Ooi, Takashi,Shirai, Yuto
, (2021/06/21)
The combination of 8-quinolinecarboxaldehyde and benzoic acid proved to be an effective catalyst system for the racemization of N-unprotected α-aryl- or α-alkyl-substituted α-amino amides. Application of this system to chemoenzymatic dynamic kinetic resolution provided an efficient access to enantiomerically pure N-acetyl-α-amino amides in good to high yields.
Unexpected hydrolytic instability of N-acylated amino acid amides and peptides
Samaritoni, J. Geno,Copes, Alexus T.,Crews, Demarcus K.,Glos, Courtney,Thompson, Andre L.,Wilson, Corydon,O'Donnell, Martin J.,Scott, William L.
, p. 3140 - 3151 (2014/05/06)
Remote amide bonds in simple N-acyl amino acid amide or peptide derivatives 1 can be surprisingly unstable hydrolytically, affording, in solution, variable amounts of 3 under mild acidic conditions, such as trifluoroacetic acid/water mixtures at room temperature. This observation has important implications for the synthesis of this class of compounds, which includes N-terminal-acylated peptides. We describe the factors contributing to this instability and how to predict and control it. The instability is a function of the remote acyl group, R2CO, four bonds away from the site of hydrolysis. Electron-rich acyl R2 groups accelerate this reaction. In the case of acyl groups derived from substituted aromatic carboxylic acids, the acceleration is predictable from the substituent's Hammett σ value. N-Acyl dipeptides are also hydrolyzed under typical cleavage conditions. This suggests that unwanted peptide truncation may occur during synthesis or prolonged standing in solution when dipeptides or longer peptides are acylated on the N-terminus with electron-rich aromatic groups. When amide hydrolysis is an undesired secondary reaction, as can be the case in the trifluoroacetic acid-catalyzed cleavage of amino acid amide or peptide derivatives 1 from solid-phase resins, conditions are provided to minimize that hydrolysis.
Method for preparing optically active amines
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Page/Page column 19, (2009/09/29)
The present invention relates to a method of preparing optically active amines and chiral amines prepared thereby. The method includes reacting an amine compound, a metal catalyst, a biocatalyst including a lipase, and an acyl donor compound in an organic solvent to obtain a chiral amide compound, and then hydrolyzing the chiral amide compound to obtain a chiral amine.
Synthesis of isotopically labeled P-site substrates for the ribosomal peptidyl transferase reaction
Zhong, Minghong,Strobel, Scott A.
, p. 603 - 611 (2008/09/17)
(Chemical Equation Presented) Isotopomers of the ribosomal P-site substrate, the trinucleotide peptide conjugate CCA-pcb (Zhong, M.; Strobel, S. A. Org. Lett. 2006, 8, 55-58), have been designed and synthesized in 26-35 steps. These include individual iso
Dynamic kinetic resolution of primary amines with a recyclable Pd nanocatalyst for racemization
Kim, Mahn-Joo,Kim, Won-Hee,Han, Kiwon,Yoon, Kyung Choi,Park, Jaiwook
, p. 1157 - 1159 (2007/10/03)
(Chemical Equation Presented) A practical procedure for the dynamic kinetic resolution (DKR) of primary amines has been developed. This procedure employs a palladium nanocatalyst as the racemization catalyst, a commercial lipase (Novozym-435) as the resol
Aqueous Solutions Containing Amino Acids and Peptides. Part 17. --Pairwise Enthalpic Coefficients for the Interaction of N-Acetyl-L-Phenylalaninamide with some N-Acetylamino Acid Amines at 25 deg C
Blackburn, G. Michael,Kent, Hilary E.,Lilley, Terence H.
, p. 2207 - 2214 (2007/10/02)
Enthalpies of dilution of N-acetyl-L-phenylalaninamide and equimolal solutions of this with N-acetylglycinamide, N-acetyl-L-alaninamide, N-acetyl- L-valinamide and N-acetyl-L-leucinamide have been determined using microcalorimetry.The results obtained were used to calculate the pairwise enthalpic coefficients for both like-like (homotactic) and like-unlike (heterotactic) solute interactions.These were then used with a group-additivity approach, which works well for these systems, to obtain information on the interaction of defined groups with each other.
Heterocycles as Masked Diamide/Dipeptide Equivalents. Formation and Reactions of Substituted 5-(Acylamino)oxazoles as Intermediates en route to the Cyclopeptide Alkaloids
Lipshutz, Bruce H.,Hungate, Randall W.,NcCarthy, Keith E.
, p. 7703 - 7713 (2007/10/02)
A variety of novel 2,4-dialkyl-5-(acylamino)oxazoles have been prepared by using either amide nitriles or diamides/dipeptides as starting materials.Ring closure calls for the use of trifluoroacetic acid/trifluoroacetic acid anhydride or an acid halide in
Asymmetric Hydrogenation with Chiral Aminophosphine-Rhodium Complexes and Chiral Recognition by Bisphosphine-Rhodium Complexes in the Asymmetric Hydrogenation of Olefins through the Chiral Helical Conformation of Phenyl Groups on the Phosphorus Atom
Onuma, Ken-ichi,Ito, Tomiyasu,Nakamura, Asao
, p. 2016 - 2019 (2007/10/02)
The asymmetric hydrogenation of α-acylaminocinnamic acids with the rhodium complex of (1R,2R)-1,2-bis(N-diphenylphosphino-N-methylamino)cyclohexane has been reported to give preferentially (S)-amino acids.On the contrary, it has been found that the enanti
THE ASYMMETRIC HYDROGENATION OF THE α-N-ACETYLAMINOCINNAMOYL DERIVATIVE OF AMINO ACIDS WITH CHIRAL BISPHOSPHINE-RHODIUM COMPLEX
Onuma, Ken-ichi,Ito, Tomiyasu,Nakamura, Asao
, p. 481 - 482 (2007/10/02)
An optical yield of the dipeptide obtained in the title reaction is affected by a chiral amino acid moiety in the substrate.
