In:
Angewandte Chemie, Wiley, Vol. 134, No. 31 ( 2022-08)
Abstract:
Non‐proteogenic amino acids and functionalized peptides are important motifs in modern drug discovery. Here we report that Ala B can serve as universal building blocks in the synthesis of a diverse collection of modified amino acids, peptides, and proteins. First, we develop the synthesis of Ala B from redox‐active esters of aspartic acid resulting in a series of β‐boronoalanine derivatives. Next, we show that Ala B can be integrated into automated oligopeptide solid‐phase synthesis. Ala B is compatible with common transformations used in preparative peptide chemistry such as native chemical ligation and radical desulfurization as showcased by total synthesis of Ala B ‐containing ubiquitin. Furthermore, Ala B reagents participate in Pd‐catalyzed reactions, including C−C cross‐couplings and macrocyclizations. Taken together, Ala B synthons are practical reagents to access modified peptides, proteins, and in the synthesis of cyclic/stapled peptides.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v134.31
DOI:
10.1002/ange.202207153
Language:
English
Publisher:
Wiley
Publication Date:
2022
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505868-5
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506609-8
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514305-6
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505872-7
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1479266-7
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505867-3
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506259-7
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