The p-methoxybenzyl ester group in peptide synthesis

1968 ◽  
Vol 21 (10) ◽  
pp. 2543 ◽  
Author(s):  
FHC Stewart
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Ester Group ◽  
Protecting Group ◽  
Chain Sequence ◽  
A Chain

p-Methoxybenzyl esters of protected amino acids and peptides have been prepared by imidazole-promoted condensation of the corresponding p-nitrophenyl esters with p-methoxybenzyl alcohol. The products included several o-nitrophenylsulphenyl dipeptide p-methoxybenzyl esters, and the use of p-methoxybenzyl as a carboxyl-protecting group was illustrated by the synthesis of a protected pentapeptide fragment of a modified insulin A-chain sequence involving selective acidic cleavage of a-nitrophenylsulphenyl.

The 2,2,2-Trichloroethyl Group for Carboxyl Protection During Peptide Synthesis

1973 ◽  
Vol 51 (2) ◽  
pp. 208-214 ◽  
Author(s):  
Bernard Marinier ◽  
Yoon C. Kim ◽  
Jean-Marie Navarre
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Peptide Synthesis ◽  
Optical Activity ◽  
Selective Removal ◽  
Acid Chlorides ◽  
Protecting Group

The 2,2,2-trichloroethyl esters of several N-carbobenzoxy-amino acids were prepared by reacting the corresponding acid chlorides with trichloroethanol and the carbobenzoxy groups were selectively removed by HBr–AcOH. The resulting esters were then coupled with various N-carbobenzoxy-amino acids or peptides using dicyclohexylcarbodiimide in acetonitrile to give N-carbobenzoxy-peptide trichloroethyl esters. The selective removal of the trichloroethyl protecting group was effected by reduction using zinc in acetic acid. The optical activity of the N-carbobenzoxy-peptides so obtained agreed well with the values reported in the literature. The overall results suggest that the 2,2,2-trichloroethyl group could be useful for carboxyl protection during peptide synthesis.

Methylphosphinyl (Dmp): A new protecting group of tyrosine suitable for peptide synthesis by use of boc-amino acids

1986 ◽  
Vol 27 (35) ◽  
pp. 4181-4184 ◽  
Author(s):  
Masaaki Ueki ◽  
Yoshiyuki Sano ◽  
Ichiro Sori ◽  
Kozo Shinozaki ◽  
Hidekazu Oyamada ◽  
...  
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Protecting Group

ChemInform Abstract: Dimethylphosphinyl (Dmp): A New Protecting Group of Tyrosine Suitablefor Peptide Synthesis by Use of Boc-Amino Acids.

ChemInform ◽  
1987 ◽  
Vol 18 (1) ◽  
Author(s):  
M. UEKI ◽  
Y. SANO ◽  
I. SORI ◽  
K. SHINOZAKI ◽  
H. OYAMADA ◽  
...  
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Protecting Group

Pentamethylbenzyl esters of α-hydroxy acids and their use in depsipeptide synthesis

1968 ◽  
Vol 21 (5) ◽  
pp. 1327 ◽  
Author(s):  
FHC Stewart
Keyword(s):  
Amino Acids ◽  
Trifluoroacetic Acid ◽  
Hydroxy Acid ◽  
Ester Group ◽  
Protecting Group ◽  
Hydroxy Acids ◽  
Acidic Conditions ◽  
Crystalline Nature

Pentamethylbenzyl esters of several a-hydroxy acids have been prepared as possible intermediates in depsipeptide synthesis. Potentially useful features of pentamethylbenzyl as a carboxyl-protecting group are the crystalline nature of the esters, and the rapid cleavage of the group under mild acidic conditions. The glycollate, lactate, and mandelate were coupled with various protected amino acids to form crystalline aminoacyl hydroxy acid derivatives. Selective cleavage of the ester group in these compounds was readily effected with cold trifluoroacetic acid, and the products were used in the synthesis of some representative protected depsipeptides.

P-Methoxybenzyl esters of amino acids-their preparation and use in peptide synthesis

1971 ◽  
Vol 24 (8) ◽  
pp. 1695 ◽  
Author(s):  
BJ Maclaren
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Ester Group

Various N-protected amino acids have been alkylated with p- methoxybenzyl chloride to give the corresponding esters. These were then converted into amino acid p-methoxybenzyl esters by selective acidolysis of the N-o-nitrophenylsulphenyl and N-trityl derivatives, or in poor yield by hydrazinolysis of the N-phthaloyl derivative. S- Benzylcysteine p-methoxybenzyl ester is obtained without racemiza- tion. These esters have been applied to the syntheses of several dipeptides, the ester group being cleaved by cold trifluoroacetic acid.

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