Get Aspects of the Merrifield Peptide Synthesis PDF

By Priv.-Doz. Dr. Christian Birr (auth.)

ISBN-10: 3642670040

ISBN-13: 9783642670046

ISBN-10: 3642670067

ISBN-13: 9783642670060

This booklet used to be written within the context of the day-by-day war of words with difficulties within the usage of polymeric helps for the synthesis of pep tides. for that reason, perspectives and reports which generally are usually not pointed out in clinical journals are accrued in those pages. the writer has intentionally mentioned intimately the prospective effect of the polymer part at the various response stipulations within the Merrifield synthesis; this element is overlooked in such a lot courses facing peptide synthesis. although, in view of the becoming physique of knowledge at the chemistry of polymer-supported peptide syntheses, the foreign readership should still regard the author's arguments as open to dialogue. i'm greatly indebted to all of my colleagues with whom i've got had the chance to cooperate in learning the opportunity of the Merrifield synthesis. specially i admire to specific my gratitude to my instructor, Professor Dr. Theodor Wieland, Heidelberg, for his boundless encouragement and aid in my ef­ forts within the box of peptide synthesis, rather in its polymer part certain model. final yet now not at the least I desire to thank pass over Hildegard Leyden. With in­ finite persistence and nice accuracy she typed the manuscript as well as her day-by-day tasks. The paintings which motivated this booklet used to be played below the auspices of the Max-Planck-Gesellschaft, of which the monetary help is gratefully ac­ knowledged.

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Example text

This example was given merely to demonstrate the advantageous properties of the Ddz protecting group for different synthetic purposes. To summarize, the masking functions in a Merrifield synthesis should be selected in such a gradation of lability that the often repeated N-terminal deprotections endanger neither the C-terminallink to the support nor the masked side functions of the growing peptide. The type of anchoring used should allow us to liberate the peptide in an entirely protected form from its support, to allow further use of the sequence in fragment condensation reactions.

These conditions, however, are seldom realized: For example, in most of the early loading experiments tertiary bases capable of reacting with chloromethyl and bromoacetyl functions were present. This undesirable side effect, which falsifies the nitrogen content of the loaded polymer, to date is eliminated by the use of tetraalkylammonium- and caesium salts of amino acids or peptides to be bound with their carboxylate function to chloromethyl- or bromoacetyl sites with formation of ester linkages.

One titration lasts about 1 hour because of the slow reaction of the glass-calomel combination of electrodes on changing potentials and is usually repeated once. To neutralize free amino groups on polymer, each equivalent of perchloric acid of the titrant transports about 2 equivalents of water into the reaction mixture. These moist conditions endanger extended Merrifield syntheses with trifunctional amino acids by proton catalyzed side reactions including detachment from polymer as well as partial acid hydrolysis of the peptide as we found.

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Aspects of the Merrifield Peptide Synthesis by Priv.-Doz. Dr. Christian Birr (auth.)

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