ChemInform Abstract: The 2-Chloro-3-indenylmethyloxycarbonyl and Benz(f)inden-3-ylmethoxycarbonyl Base-Sensitive Amino-Protecting Groups. Application to an Inverse Merrifield Approach to Peptide Synthesis.

ChemInform ◽  
1990 ◽  
Vol 21 (28) ◽  
Author(s):  
L. A. CARPINO ◽  
B. J. COHEN ◽  
Y.-Z. LIN ◽  
K. E. JUN. STEPHENS ◽  
S. A. TRIOLO
Keyword(s):  
Peptide Synthesis ◽  
Protecting Groups

Selective acid hydrolysis of 2,4,6-trimethylbenzyl esters and its application in peptide synthesis

1966 ◽  
Vol 19 (8) ◽  
pp. 1511 ◽  
Author(s):  
FHC Stewart
Keyword(s):  
Acid Hydrolysis ◽  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Ester Group ◽  
Protecting Groups ◽  
Alkaline Conditions ◽  
Hydrolysis Of

Experiments with various N-acylamino acid 2,4,6-trimethylbenzyl esters have shown that the ester group is cleaved selectively by cold trifluoroacetic acid without affecting benzyloxycarbonyl, formyl, or phthaloyl amino-protecting groups present. The possible value of this selective behaviour in peptide syntheses where the use of alkaline conditions would be detrimental is illustrated by the synthesis of certain dipeptide derivatives.

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.

scholarly journals Role of capping in peptide synthesis

2020 ◽  
Vol 11 (4) ◽  
pp. 5225-5228
Author(s):  
Deepshikha Verma ◽  
Pillai V N R ◽  
Giriraj Tailor
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Protecting Groups ◽  
Amino Groups ◽  
Peptide Chemistry ◽  
Fmoc Spps ◽  
Reliable Methods ◽  
Important Test

Protecting groups like Fmoc and coupling both steps are essential to monitoring the Fmoc SPPS (Solid Phase Peptide Synthesis) reaction completion. Reliable methods are used to detect the unreacted number of amino groups for monitoring these two essential reaction steps of coupling and cleavage. The ability to detect the complete coupling, incomplete coupling or failure of coupling we use many colour tests in the laboratory and based on this the Fmoc peptide chemistry allows the control of the completion of the Fmoc cleavage. The most important test used is the Kaiser test and highly recommended to monitor the coupling and cleavage steps. If the result of colour tests is positive after coupling, then the second coupling should be performed. Then again use the colour test to detect the level of coupling. If the result is still slightly positive, repeat coupling with the smaller modification of reagents such as used PyBOP instead of HOBT AND HOAT. These colour tests help in revealing the presence of unreacted amino-functional groups. Thus, we need to block these free N-terminal of amino- acids which help in avoiding the making of deletion of sequence.

Novel cysteine protecting groups for the Nα-9-fluorenylmethyloxycarbonyl (Fmoc) strategy of peptide synthesis

Peptides ◽  
1992 ◽  
pp. 605-606 ◽  
Author(s):  
Mark C. Munson ◽  
Carlos García-Echeverría ◽  
Fernando Albericio ◽  
George Barany
Keyword(s):  
Peptide Synthesis ◽  
Protecting Groups ◽  
Fmoc Strategy

The Application of Recently Developed Amino Protecting Groups in Peptide Synthesis

1983 ◽  
pp. 125-128 ◽  
Author(s):  
Wolfgang Voelter ◽  
Jürgen Müller ◽  
Charles Beni ◽  
Wolfgang Heinzel ◽  
Hubert Kaibacher ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Protecting Groups

New Methods in Peptide Synthesis. I. Tritylsulfenyl ando-Nitrophenylsulfenyl Groups as N-Protecting Groups

1963 ◽  
Vol 85 (22) ◽  
pp. 3660-3666 ◽  
Author(s):  
Leonidas. Zervas ◽  
Dimitrios. Borovas ◽  
Euthymios. Gazis
Keyword(s):  
Peptide Synthesis ◽  
Protecting Groups ◽  
New Methods
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