Piperonyl ester derivatives of amino acids and their use in peptide synthesis

1971 ◽  
Vol 24 (10) ◽  
pp. 2193 ◽  
Author(s):  
FHC Stewart
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Derivatives Of

N-Methylamino Acids in Peptide Synthesis. II. A New Synthesis of N-Benzyloxycarbonyl, N-Methylamino Acids

1973 ◽  
Vol 51 (12) ◽  
pp. 1915-1919 ◽  
Author(s):  
John R. McDermott ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acids ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Side Chains ◽  
Butyl Group ◽  
New Synthesis ◽  
Derivatives Of

Reaction of N-benzyloxycarbonyl derivatives of aliphatic amino acids, and threonine, aspartic, and glutamic acids whose side-chains were protected with the t-butyl group, gave the corresponding N-methylamino acid derivatives in good yields. The methionine derivative could be obtained by using only one mol of methyl iodide. Derivatives of threonine, and aspartic and glutamic acids whose side-chains were not protected could not be methylated. Analysis of the crude products of methylation in three cases showed that they contained 0–1% of racemized material.

Preparation of ketimine derivatives of amino acids for peptide synthesis

1974 ◽  
Vol 27 (9) ◽  
pp. 2047 ◽  
Author(s):  
B Halpern ◽  
AP Hope
Keyword(s):  
Amino Acids ◽  
Hydrogen Bond ◽  
Acid Hydrolysis ◽  
Peptide Synthesis ◽  
Room Temperature ◽  
Mild Conditions ◽  
Protein Amino Acids ◽  
Intramolecular Hydrogen ◽  
Derivatives Of ◽  
Strong Intramolecular Hydrogen Bond

Condensates of some 2-hydroxyaryl ketones with protein amino acids have been prepared. The reaction has been shown to proceed without racemization and the derivatives have been isolated as free acids. Their unusual stability is ascribed to the presence of a strong intramolecular hydrogen bond. The N-arylmethylene function is cleaved under mild conditions of acid hydrolysis. Ketimines derived from D-phenylglycine decarboxylate at room temperature.

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