Syntheses of amino acids and related compounds. 19. New versatile syntheses of 2-substituted-2-amino acid and 2,3-dehydro-2-amino acid derivatives

1979 ◽  
Vol 44 (3) ◽  
pp. 391-395 ◽  
Author(s):  
Yasuhiko Ozaki ◽  
Tameo Iwasaki ◽  
Hiroshi Horikawa ◽  
Muneji Miyoshi ◽  
Kazuo Matsumoto
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Related Compounds

scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt - Eistert Procedure

2005 ◽  
Vol 58 (11) ◽  
pp. 778 ◽  
Author(s):  
Andrew B. Hughes ◽  
Brad E. Sleebs
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Reductive Cleavage ◽  
High Yield ◽  
Amino Acid Derivatives ◽  
Peptide Therapeutics

N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.

Chiral sensors for determining the absolute configurations of α-amino acid derivatives

2018 ◽  
Vol 16 (37) ◽  
pp. 8311-8317 ◽  
Author(s):  
Zhongxiang Chen ◽  
Hongjun Fan ◽  
Shiwei Yang ◽  
Guangling Bian ◽  
Ling Song
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
H Nmr ◽  
The Absolute

Two simple 1H NMR tests give the absolute configurations of α-amino acids.

Chelating polymers. I. The synthesis and acid dissociation behavior of several N-(p-vinylbenzenesulfonyl)-substituted diaminopolyacetic acid monomers, monomeric analogues, and related intermediates

1970 ◽  
Vol 48 (1) ◽  
pp. 163-175 ◽  
Author(s):  
R. M. Genik-Sas-Berezowsky ◽  
I. H. Spinner
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Dissociation Constants ◽  
Acid Dissociation ◽  
Inductive Effects ◽  
Cyclic Amide ◽  
Amino Acid Analogues ◽  
Related Compounds ◽  
Chelating Polymers ◽  
Made In

Two new chelating monomers, N-(p-vinylbenzenesulfonyl)1,2-diaminoethane-N′,N′-diacetic (SS-EDDA) and -N,N′,N′-triacetic (SS-ED3A) acids, as well as several monomeric analogues and related intermediates have been prepared. In addition, 2-oxo-1-piperazine acetic (S-KP), 3-oxo-1-piperazine acetic (U-KP), and 2-oxo-1,4-piperazine diacetic (3-KP) acids have been synthesized and the interconvertibility between these cyclic amides and their unsubstituted linear amino acid analogues, ethylene-diamine-N,N′-diacetic (S-EDDA), -N,N-diacetic (U-EDDA), and -N,N,N′-triacetic (ED3A) acids respectively, was demonstrated.The acid dissociation constants of the various amino acids were determined potentiometrically at 25° and μ = 0.1 M(KNO3) and the results were compared with the hydrogen ion affinities of related compounds. Dissociation schemes were proposed for all the compounds based on these results. Rationalizations of the linear amino acid and the cyclic amide dissociation constants were made in terms of the effects of cyclization and the inductive effects of neighboring groups. These rationalizations were found to be helpful in clarifying the dissociation schemes previously proposed for several of the linear amino acids.

Formation and occurrence of N-malonylphenylalanine and related compounds in plants

1968 ◽  
Vol 46 (8) ◽  
pp. 797-806 ◽  
Author(s):  
N. Rosa ◽  
A. C. Neish
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Glutamic Acid ◽  
Plant Species ◽  
Isolation Procedure ◽  
Plant Kingdom ◽  
Feeding Experiments ◽  
Leucine Isomers ◽  
Related Compounds

Shoots of barley seedlings when fed D-phenylalanine convert the amino acid to N-malonylphenylalanine. Some N-acetylphenylalanine is obtained at the same time but this may be an artifact of the isolation procedure since it is readily formed by decarboxylation of the malonylphenylalanine. Feeding experiments with the D- and L-isomers of phenylalanine, valine, leucine, isoleucine, tyrosine, tryptophan, alanine, and glutamic acid showed that barley shoots form the malonyl derivative from all the D-isomers whereas little, if any, is formed from the L-isomers. Similar experiments with phenylalanine and leucine isomers, using seven different plant species, showed that the ability to conjugate the D-isomers (but not the L-isomers) was found in all of the plants tested. It was also observed that the ether-soluble acidic conjugates of a variety of amino acids, possibly malonyl derivatives, occur widely throughout the plant kingdom.

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