Der 2,4,6-Triisopropylbenzolsulfonyl(Tip)-Rest, eine neue Schutzgruppe für die Guanidinofunktion von Arginin / The 2,4,6-Triisopropylbenzenesulfonyl Residue, a New Protecting Group for the Guanidino Function of Arginine

1987 ◽  
Vol 42 (12) ◽  
pp. 1591-1594 ◽  
Author(s):  
Hartmut Echner ◽  
Wolfgang Voelter
Keyword(s):  
Peptide Synthesis ◽  
Sulfonyl Chloride ◽  
Trifluoromethanesulfonic Acid ◽  
High Yield ◽  
Protecting Group

AbstractThe 2.4.6-triisopropylbenzenesulfonyl group is introduced in high yield into the guanidino function of arginine by the reaction of Na-protected arginine with 2.4.6-triisopropylbenzene-sulfonyl chloride. This protecting group was found to be cleaved by commonly used reagents used in peptide synthesis like methanesulfonic, trifluoromethanesulfonic acid or mixtures of tri-fluoroacetic with methanesulfonic or trifluoromethanesulfonic acid.

o-Nitrobenzoyl group as a new amino protecting group for peptide synthesis and the synthesis of some anthranilyl peptides

Tetrahedron ◽  
1973 ◽  
Vol 29 (4) ◽  
pp. 625-628 ◽  
Author(s):  
A.K. Koul ◽  
J.M. Bachhawat ◽  
B. Prashad ◽  
N.S. Ramegowda ◽  
A.K. Mathur ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Protecting Group

Synthesis of oxytocin, arginine-vasopressin and its deamino-analogue using 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur

1981 ◽  
Vol 46 (1) ◽  
pp. 286-299 ◽  
Author(s):  
František Brtník ◽  
Milan Krojidlo ◽  
Tomislav Barth ◽  
Karel Jošt
Keyword(s):  
Peptide Synthesis ◽  
Hydrogen Fluoride ◽  
Sulfur Atom ◽  
Arginine Vasopressin ◽  
Liquid Hydrogen ◽  
Trifluoromethanesulfonic Acid ◽  
Protecting Groups ◽  
Mild Conditions

Preparation of oxytocin, arginine-vasopressin and its deamino-analogue serves as an example of use of 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur atom in the peptide synthesis. This modified benzyl group is sufficiently stable under conditions of solvolytic removal of common amino-protecting groups and it can be cleaved off under mild conditions with liquid hydrogen fluoride or trifluoromethanesulfonic acid.

The 2-chloro-3-indenylmethyloxycarbonyl and benz[f]inden-3-ylmethyloxycarbonyl base-sensitive amino-protecting group. Application to an inverse Merrifield approach to peptide synthesis

1990 ◽  
Vol 55 (1) ◽  
pp. 251-259 ◽  
Author(s):  
Louis A. Carpino ◽  
Beri J. Cohen ◽  
Yao Zhong Lin ◽  
Kenton E. Stephens ◽  
Salvatore A. Triolo
Keyword(s):  
Peptide Synthesis ◽  
Protecting Group

ChemInform Abstract: New Strategies for an Efficient Removal of the 9-Fluorenylmethoxycarbonyl (Fmoc) Protecting Group in the Peptide Synthesis.

ChemInform ◽  
2010 ◽  
Vol 31 (16) ◽  
pp. no-no
Author(s):  
Antonella Leggio ◽  
Angelo Liguori ◽  
Anna Napoli ◽  
Carlo Siciliano ◽  
Giovanni Sindona
Keyword(s):  
Peptide Synthesis ◽  
Protecting Group ◽  
Efficient Removal ◽  
Fmoc Protecting Group ◽  
New Strategies
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