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.

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.

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.

scholarly journals Revisiting NO2 as Protecting Group of Arginine in Solid-Phase Peptide Synthesis

2020 ◽  
Vol 21 (12) ◽  
pp. 4464
Author(s):  
Mahama Alhassan ◽  
Ashish Kumar ◽  
John Lopez ◽  
Fernando Albericio ◽  
Beatriz G. de la Torre
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Reaction ◽  
Reducing Agent ◽  
Protecting Groups ◽  
Side Chain ◽  
Protecting Group ◽  
Mild Acid

The protection of side-chain arginine in solid-phase peptide synthesis requires attention since current protecting groups have several drawbacks. Herein, the NO2 group, which is scarcely used, has been revisited. This work shows that it prevents the formation of δ-lactam, the most severe side-reaction during the incorporation of Arg. Moreover, it is stable in solution for long periods and can be removed in an easy-to-understand manner. Thus, this protecting group can be removed while the protected peptide is still anchored to the resin, with SnCl2 as reducing agent in mild acid conditions using 2-MeTHF as solvent at 55 °C. Furthermore, we demonstrate that sonochemistry can facilitate the removal of NO2 from multiple Arg-containing peptides.

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

Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides

Synthesis ◽  
2020 ◽  
Author(s):  
Ryan Moreira ◽  
Michael Noden ◽  
Scott D. Taylor
Keyword(s):  
Amino Acids ◽  
Natural Products ◽  
Total Synthesis ◽  
Cyclic Peptides ◽  
Protecting Groups ◽  
Side Chain ◽  
Coupling Reactions ◽  
Protecting Group

AbstractAzido acids are important synthons for the synthesis of complex peptides. As a protecting group, the azide moiety is atom-efficient, easy to install and can be reduced in the presence of many other protecting groups, making it ideal for the synthesis of branched and/or cyclic peptides. α-Azido acids are less bulky than urethane-protected counterparts and react more effectively in coupling reactions of difficult-to-form peptide and ester bonds. Azido acids can also be used to form azoles on complex intermediates. This review covers the synthesis of azido acids and their application to the total synthesis of complex peptide natural products.1 Introduction2 Synthesis of α-Azido Acids2.1 From α-Amino Acids or Esters2.2 Via α-Substitution2.3 Via Electrophilic Azidation2.4 Via Condensation of N-2-Azidoacetyl-4-Phenylthiazolidin- 2-Thi one Enolates with Aldehydes and Acetals2.5 Synthesis of α,β-Unsaturated α-Azido Acids and Esters3 Synthesis of β-Azido Acids3.1 Preparation of Azidoalanine and 3-Azido-2-aminobutanoic Acids3.2 General Approaches to Preparing β-Azido Acids Other Than Azi doalanine­ and AABA4 Azido Acids in Total Synthesis4.1 α-Azido Acids4.2 β-Azido Acids and Azido Acids Containing an Azide on the Side Chain5 Conclusions

Resin-free peptide synthesis mediated by tri(4-benzoylphenyl) phosphate (TBP) derivatives as small-molecule supports

2020 ◽  
Vol 7 (4) ◽  
pp. 689-696 ◽  
Author(s):  
Haidi Li ◽  
Jie Chao ◽  
Guang Tian ◽  
Jaafar Hasan ◽  
Yatao Jin ◽  
...  
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Small Molecule ◽  
Protecting Groups ◽  
Free Peptide

A series of novel tri(4-benzoylphenyl) phosphate (TBP) derivatives with unique precipitation-inducing properties were synthesized and used as C-terminal protecting groups of amino acids and recyclable supports in peptide synthesis.

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