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M. Feurer

Bio: M. Feurer is an academic researcher from Ciba Specialty Chemicals. The author has contributed to research in topics: Acylation & Aminolysis. The author has an hindex of 4, co-authored 4 publications receiving 264 citations.

Papers
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Journal ArticleDOI
TL;DR: In this article, a number of activated esters of hippuric acid are compared and the best acylating agent seems to be the cyanomethylester which is an easily accessible, cristalline, and stable compound, reacting easily with benzylamine at room temperature.
Abstract: Introduction of electron-attracting substituents into the alcoholic component of methyl-hippurate leads to activated esters which are characteristic acylating agents. A number of activated esters of hippuric acid are compared. The best acylating agent seems to be the cyanomethylester which is an easily accessible, cristalline, and stable compound, reacting easily with benzylamine at room temperature.

109 citations

Journal ArticleDOI
TL;DR: A number of activated esters of amino acid and peptide derivatives were reacted with various organic amines, including amino acid esters, and good yields obtained, and the mild reaction conditions make it seem possible that the activated ester method of acylation may be of good use in peptide synthesis as discussed by the authors.
Abstract: A number of activated esters of amino acid and peptide derivatives were reacted with various organic amines, including amino acid esters. The good yields obtained, and the mild reaction conditions make it seem possible that the activated ester method of acylation may be of good use in peptide synthesis. Aminolysis by aromatic amines and by secondary amines proceeds only slowly, but the reaction can be greatly facilitated through the catalytic action of strong tertiary amines and of acids.

68 citations

Journal ArticleDOI
TL;DR: In this article, the synthesis of cristalline cyanomethyl esters and some other activated esters of amino acid and peptide derivatives are described. But the synthesisation of these esters is not discussed.
Abstract: The syntheses of a number of cristalline cyanomethyl esters and of some other activated esters of aminoacid and peptide derivatives are described.

50 citations

Journal ArticleDOI
TL;DR: In this paper, a cyanomethyl ester of (N-carbobenzoxy-S-benzyl-L-cysteinyl)-L-tyrosine was used for preparing relatively complicated peptides, especially if acetic acid is used as a catalyst.
Abstract: A study on the synthesis of (N-carbobenzoxy-S-benzyl-L-cysteinyl)-L-tyrosyl-L-isoleucine (XII) by the activated ester method has shown that the cyanomethyl esters prove useful for preparing relatively complicated peptides, especially if acetic acid is used as a catalyst. An important feature of the method is the fact that the cyanomethyl ester of (N-carbobenzoxy-S-benzyl-L-cysteinyl)-L-tyrosine on hydrolysis or aminolysis produces derivatives of L-cysteinyl-L-tyrosine without any signs of racemisation.

41 citations


Cited by
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Journal ArticleDOI
TL;DR: Peptide Coupling Reagents, More than a Letter Soup Ayman El-Faham* and Fernando Albericio* Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain.
Abstract: Peptide Coupling Reagents, More than a Letter Soup Ayman El-Faham* and Fernando Albericio* Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain Alexandria University, Faculty of Science, Department of Chemistry, P.O. Box 426, Ibrahimia, 21321 Alexandria, Egypt CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain. Department of Organic Chemistry, University of Barcelona, Martí i Franqu es 1-11, 08028-Barcelona, Spain

839 citations

Journal ArticleDOI
TL;DR: This protocol for solid-phase peptide synthesis (SPPS) is based on the widely used Fmoc/tBu strategy, activation of the carboxyl groups by aminium-derived coupling reagents and use of PEG-modified polystyrene resins.
Abstract: This protocol for solid-phase peptide synthesis (SPPS) is based on the widely used Fmoc/tBu strategy, activation of the carboxyl groups by aminium-derived coupling reagents and use of PEG-modified polystyrene resins. A standard protocol is described, which was successfully applied in our lab for the synthesis of the corticotropin-releasing factor (CRF), >400 CRF analogs and a countless number of other peptides. The 41-mer peptide CRF is obtained within approximately 80 working hours. To achieve the so-called difficult sequences, special techniques have to be applied in order to reduce aggregation of the growing peptide chain, which is the main cause of failure for peptide chemosynthesis. Exemplary application of depsipeptide and pseudoproline units is shown for synthesizing an extremely difficult sequence, the Asn(15) analog of the WW domain FBP28, which is impossible to obtain using the standard protocol.

461 citations

Journal ArticleDOI
TL;DR: Pentafluorophenyl acrylate and -methacrylate were polymerized using AIBN as a thermal initiator and the obtained polymers were soluble polymeric active esters that could be used for the preparation of multifunctional polymers as discussed by the authors.

333 citations

Journal ArticleDOI
TL;DR: In this paper, two different research areas of activated esters in polymer science are discussed: (i) the preparation of defined reactive polymer architectures by controlled polymerization techniques and (ii) the prepared reactive thin films.
Abstract: Monomers bearing an activated ester group can be polymerized under various controlled polymerization techniques, such as ATRP, NMP, RAFT polymerization, or ROMP. Combining the functionalization of polymers via polymeric activated esters with these controlled polymerization techniques generate possibilities to realize highly functionalized polymer architectures. Within this highlight two different research areas of activated esters in polymer science will be discussed: (i) the preparation of defined reactive polymer architectures by controlled polymerization techniques and (ii) the preparation of defined reactive thin films. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 6677–6687, 2008

265 citations