Facile Synthesis of Highly FunctionalizedN-Methyl Amino Acid Esters without Side-Chain Protection

2005 ◽  
Vol 7 (19) ◽  
pp. 4111-4112 ◽  
Author(s):  
Kimberly N. White ◽  
Joseph P. Konopelski
Keyword(s):  
Amino Acid ◽  
Side Chain ◽  
Amino Acid Esters ◽  
Facile Synthesis ◽  
Acid Esters

N-Arylation of Amino Acid Esters to Expand Side Chain Diversity in Ketoxime Peptide Ligations

2019 ◽  
Vol 85 (3) ◽  
pp. 1748-1755
Author(s):  
Hailey A. Young ◽  
Quibria A. E. Guthrie ◽  
Caroline Proulx
Keyword(s):  
Amino Acid ◽  
Side Chain ◽  
Amino Acid Esters ◽  
Acid Esters

Succinimidyl esters of fatty acids for amino acid acylations

1976 ◽  
Vol 54 (5) ◽  
pp. 733-737 ◽  
Author(s):  
Alenka Paquet
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Amino Acid ◽  
Free Amino ◽  
Side Chain ◽  
Amino Acid Esters ◽  
Amino Group ◽  
Acyl Chlorides ◽  
Hydroxysuccinimide Esters ◽  
Acid Esters

Fatty acid N-hydroxysuccinimide esters have been prepared from the thallium(I) salt of N-hydroxysuccinimide and the corresponding acyl chlorides in essentially quantitative yields. These active esters were used for acylation of amino acid esters in organic solvents, or of free amino acids in aqueous medium. The title compounds were found to be selective towards the side chain amino group of lysine. An efficient preparation of ε-N-benzyloxycarbonyl-L-lysine using benzyl succinimidyl carbonate is described.

The Effect of N-Substitution on the Rates of Saponification of Some Amino Acid Esters

1971 ◽  
Vol 49 (21) ◽  
pp. 3468-3476 ◽  
Author(s):  
Jocelyn E. Purdie ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acid ◽  
Methyl Esters ◽  
Activation Parameters ◽  
Side Chain ◽  
Amino Acid Esters ◽  
Trans Isomers ◽  
Cis And Trans Isomers ◽  
Cis And Trans ◽  
Hydrolysis Of ◽  
Acid Esters

The saponification rates (measured at 25 ° by a titrimetric method) of the unprotonated forms of the methyl esters of glycine, alanine, leucine, valine, and phenylalanine were compared with those of the N-methyl, the N-acetyl, and the N-acetyl, N-methylamino acid analogues. N-Acetylation slightly increased or decreased the rate but N-methylation caused a reduction by as much as a factor of ten, depending on the complexity of the side-chain. The esters of the N-acetyl, N-methylamino acids, which exist as cis and trans isomers, were saponified at rates intermediate between those of the esters of the N-acetylamino acids and N-methylamino acids. Activation parameters were obtained for the phenylalanine and leucine derivatives. N-Methylation resulted in an increase in ΔH≠ and ΔS≠ which was attributed in part to solvation effects. The hydrolysis of the cationic esters of glycine and alanine was still evident at pH 11.0. N-Methylation had little effect on the rates of saponification of the charged forms.

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