Download Protection of Functional Groups in Peptide Synthesis. The by Erhard Gross, Johannes Meienhofer PDF

By Erhard Gross, Johannes Meienhofer

Hardcover booklet provides cutting-edge (ca 1981) in security of sensible teams in peptide synthesis. quantity three.

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By Erhard Gross, Johannes Meienhofer

Hardcover booklet provides cutting-edge (ca 1981) in security of sensible teams in peptide synthesis. quantity three.

Show description

Read Online or Download Protection of Functional Groups in Peptide Synthesis. The Peptides: Analysis, Synthesis, Biology PDF

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Extra info for Protection of Functional Groups in Peptide Synthesis. The Peptides: Analysis, Synthesis, Biology

Sample text

2-Halide-Substituted-Ethyloxycarbonyl Groups. This type of amine protection has been applied when smooth deprotection in neutral solution was desirable. The chlorocarbonates of these compounds are stable reagents for the acylation of amine groups. The deprotection of 2-bromoethyloxycarbonyl (Bee) amine compounds (27, see Table V) (Brugger, 1965; Büchi, 1965) by AgC10 4 in acqueous acetone is so mild that protecting groups that are sensitive to acids, bases, or hydrogénation are not affected. Therefore, the main application of these residues lies in the preparation of intermediates bearing labile protection.

With trifluoroacetic acid anhydride in trifluoroacetic acid Na-trifluoroacetyl derivatives are exclusively formed (Weygand and Geiger, 1956). Acetic acid anhydride in formic acid yields the α-formyl derivative (Hofmann et ai, 1960). Another route to α-protection proceeds via the ω-benzylidene compounds, which can be isolated without difficulty (Bezas and Zervas, 1961; Wünsch and Zwick, 1964). After protection of the α-amino group, the benzylidene residue is removed by treatment with acid. The liberated ωamino group is then derivatized with the second protecting group.

More advantageously, the course of the hydrogénation can be controlled by automated titration of the liberated amine group at about pH 4, for example, with HC1 or toluenesulfonic acid. The search for additional deblocking conditions led to the cleavage by HBr in acetic acid as a standard method (Ben Ishai and Berger, 1952). Sakakibara et al. (1967) introduced the liquid hydrogen fluoride cleavage, which by now is generally used for the removal of all acid-sensitive protecting groups. A related reagent is pyridinium polyhydrogen fluoride (Matsuura et αί, 1976).

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