ChemInform Abstract: Trialkylsilanes as Scavengers for the Trifluoroacetic Acid Deblocking of Protecting Groups in Peptide Synthesis.

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.

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Trialkylsilanes as scavengers for the trifluoroacetic acid deblocking of protecting groups in peptide synthesis

Tetrahedron Letters ◽

10.1016/s0040-4039(00)99113-5 ◽

1989 ◽

Vol 30 (21) ◽

pp. 2739-2742 ◽

Cited By ~ 165

Author(s):

Daniel A. Pearson ◽

Mary Blanchette ◽

Mary Lou Baker ◽

Cathy A. Guindon

Keyword(s):

Peptide Synthesis ◽

Trifluoroacetic Acid ◽

Protecting Groups

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Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Single-Protected α,ω-Diaminoalkanes

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19992035 ◽

1999 ◽

Vol 64 (12) ◽

pp. 2035-2043 ◽

Cited By ~ 2

Author(s):

Vladimír Pouzar ◽

Ivan Černý ◽

Pavel Drašar

Keyword(s):

Trifluoroacetic Acid ◽

Protecting Groups ◽

Oxime Group ◽

Amino Groups ◽

New Approach ◽

Terminal Amino ◽

Oxime Derivatives

New approach to the synthesis of steroid oximes bearing O-substituents with terminal amino groups was described. The easily accessible steroid O-(carboxymethyl)oximes were reacted with single-protected Boc-α,ω-diaminoalkanes to give corresponding amide intermediates. From them the Boc protecting groups were cleaved with trifluoroacetic acid to afford the desired steroid derivatives with terminal amino groups. The procedure was succesfully tested on steroids with O-(carboxymethyl)oxime group in positions 7 and 17. The decomposition of target products was observed during deprotection of substituted 19-oximes.

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

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19810286 ◽

1981 ◽

Vol 46 (1) ◽

pp. 286-299 ◽

Cited By ~ 6

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.

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Syntheses with 2-Phosphonioethoxycarbonyl Protecting Groups: Peptide Synthesis in Water

Angewandte Chemie International Edition in English ◽

10.1002/anie.197800671 ◽

1978 ◽

Vol 17 (1) ◽

pp. 67-68 ◽

Cited By ~ 20

Author(s):

Horst Kunz

Keyword(s):

Peptide Synthesis ◽

Protecting Groups

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ChemInform Abstract: Orthogonal Protecting Groups for N-α-Amino and C-Terminal Carboxyl Functions in Solid-Phase Peptide Synthesis

ChemInform ◽

10.1002/chin.200119257 ◽

2001 ◽

Vol 32 (19) ◽

pp. no-no

Author(s):

Fernando Albericio

Keyword(s):

Peptide Synthesis ◽

Solid Phase ◽

Solid Phase Peptide Synthesis ◽

Protecting Groups

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ChemInform Abstract: Mechanisms for the Removal of Benzyl Protecting Groups in Synthetic Peptides by Trifluoromethanesulfonic Acid - Trifluoroacetic Acid - Dimethyl Sulfide.

Chemischer Informationsdienst ◽

10.1002/chin.198652281 ◽

1986 ◽

Vol 17 (52) ◽

Author(s):

J. P. TAM ◽

W. F. HEATH ◽

R. B. MERRIFIELD

Keyword(s):

Trifluoroacetic Acid ◽

Synthetic Peptides ◽

Dimethyl Sulfide ◽

Trifluoromethanesulfonic Acid ◽

Protecting Groups

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Role of capping in peptide synthesis

International Journal of Research in Pharmaceutical Sciences ◽

10.26452/ijrps.v11i4.3134 ◽

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.

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