N-terminal cysteine bioconjugation with (2-cyanamidophenyl)boronic acids enables the direct formation of benzodiazaborines on peptides

Padanha, R. ; Cavadas, R. A. N. ; Merino, P. (Universidad de Zaragoza) ; António, J. P. M. ; Gois, P. M. P.

Resumen: Benzodiazaborines (BDABs) have emerged as a valuable tool to produce stable and functional bioconjugates via a click-type transformation. However, the current available methods to install them on peptides lack bioorthogonality, limiting their applications. Here, we report a strategy to install BDABs directly on peptide chains using (2-cyanamidophenyl)boronic acids (2CyPBAs). The resulting BDAB is stabilized through the formation of a key intramolecular B–N bond. This technology was applied in the selective modification of N-terminal cysteine-containing functional peptides.

Idioma: Inglés

DOI: 10.1021/acs.orglett.3c01835

Año: 2023

Publicado en: ORGANIC LETTERS 25, 29 (2023), 5476-5480
ISSN: 1523-7060

Factor impacto JCR: 4.9 (2023)

Categ. JCR: CHEMISTRY, ORGANIC rank: 4 / 58 = 0.069 (2023) - Q1 - T1

Factor impacto CITESCORE: 9.3 - Biochemistry (Q1) - Organic Chemistry (Q1) - Physical and Theoretical Chemistry (Q1)

Factor impacto SCIMAGO: 1.245 - Biochemistry (Q1) - Physical and Theoretical Chemistry (Q1) - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E34-20R
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-104090RB-100

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)