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Solid‐phase synthesis of peptide β‐aminoboronic acids
Author(s) -
Soor Harjeet S.,
Hansen Jonas,
Diaz Diego B.,
Appavoo Solomon,
Yudin Andrei K.
Publication year - 2019
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.533
H-Index - 7
ISSN - 2475-8817
DOI - 10.1002/pep2.24072
Subject(s) - peptide , boronic acid , combinatorial chemistry , chemistry , peptide synthesis , solid phase synthesis , conjugate , amino acid , biochemistry , mathematical analysis , mathematics
Peptide/boronic acid conjugates are attractive scaffolds for chemical probe discovery and drug design. There are only a few reactions that allow for rapid incorporation of boron into peptides. Herein, we report a new approach towards the synthesis of peptide β‐aminoboronic acids on solid support using 2‐chlorotrityl resin and solid‐phase peptide synthesis techniques with only one purification required. Evaluation of model compounds demonstrate the stability of peptide boronic acids toward degradation at physiological pH. This straightforward conjugation process should allow access to a wide range of peptide boronic acid scaffolds for both synthetic and medicinal use.