Amino acids and peptides. Part 45. Development of a new Nπ-protecting group of histidine, Nπ-(1-adamantyloxymethyl)histidine, and its evaluation for peptide synthesis

1996 ◽  
pp. 2139-2143 ◽  
Author(s):  
Yoshio Okada ◽  
Jidong Wang ◽  
Takeshi Yamamoto ◽  
Yu Mu ◽  
Toshio Yokoi
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Protecting Group

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

A New Amino Protecting Group for Amino-acids in Peptide Synthesis

Nature ◽  
1964 ◽  
Vol 202 (4932) ◽  
pp. 592-593 ◽  
Author(s):  
B. HALPERN ◽  
L. B. JAMES
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Protecting Group

p-Azobenzenecarboxamidomethyl Esters - New Colored Hydrophobic Carboxyl Protecting Groups in Peptide Synthesis

1992 ◽  
Vol 57 (7) ◽  
pp. 1495-1504 ◽  
Author(s):  
Valentin G. Zhuravlev ◽  
Anatolii A. Mazurov ◽  
Sergei A. Andronati
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Potassium Carbonate ◽  
Protecting Groups ◽  
Protecting Group ◽  
Peptide Chemistry

p-Azobenzenecarboxamidomethyl esters (OAbc esters) of several α-amino acids have been synthesized and characterized. Their application in peptide chemistry as a colored alkali labile carboxyl protecting group was demonstrated. The esters are compatible with commonly used protecting groups. They are removed with aqueous potassium carbonate in 15-20 min.

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