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Synthesis and comparative properties of two amide-generating resin linkers for use in solid phase peptide synthesis

✍ Scribed by Fang-Kun Deng; Kalyaneswar Mandal; Sam Luisier; Stephen B. H. Kent

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
347 KB
Volume
16
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

Well‐characterized resins of high purity are critical for effective solid phase peptide synthesis (SPPS). The quality of commercial (4‐methyl)benzhydrylamine‐resin (MBHA‐resin), used for the synthesis of peptide amides, is not consistent and residual ketone functionalities are frequently present. Such ketone or aldehyde impurities lead to the formation of acylation‐resistant deletion peptides in SPPS. To avoid these undesirable side reactions, we have optimized the preparation of two amide‐generating linkers, which, in combination with aminomethyl‐resin prepared directly from polystyrene resin, serve as alternatives to MBHA‐resin for peptide amide synthesis. Then we have explored their comparative properties in SPPS. Use of sonication in reductive amination facilitated the synthesis of both benzhydrylamine (BHA) and MBHA linkers. Copyright © 2010 European Peptide Society and John Wiley & Sons, Ltd.

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