000126945 001__ 126945
000126945 005__ 20241125101142.0
000126945 0247_ $$2doi$$a10.1021/acs.orglett.3c01835
000126945 0248_ $$2sideral$$a134446
000126945 037__ $$aART-2023-134446
000126945 041__ $$aeng
000126945 100__ $$aPadanha, R.
000126945 245__ $$aN-terminal cysteine bioconjugation with (2-cyanamidophenyl)boronic acids enables the direct formation of benzodiazaborines on peptides
000126945 260__ $$c2023
000126945 5060_ $$aAccess copy available to the general public$$fUnrestricted
000126945 5203_ $$aBenzodiazaborines (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.
000126945 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E34-20R$$9info:eu-repo/grantAgreement/ES/MICINN/PID2019-104090RB-100
000126945 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000126945 590__ $$a4.9$$b2023
000126945 592__ $$a1.245$$b2023
000126945 591__ $$aCHEMISTRY, ORGANIC$$b4 / 58 = 0.069$$c2023$$dQ1$$eT1
000126945 593__ $$aBiochemistry$$c2023$$dQ1
000126945 593__ $$aPhysical and Theoretical Chemistry$$c2023$$dQ1
000126945 593__ $$aOrganic Chemistry$$c2023$$dQ1
000126945 594__ $$a9.3$$b2023
000126945 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000126945 700__ $$aCavadas, R. A. N.
000126945 700__ $$0(orcid)0000-0002-2202-3460$$aMerino, P.$$uUniversidad de Zaragoza
000126945 700__ $$aAntónio, J. P. M.
000126945 700__ $$aGois, P. M. P.
000126945 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000126945 773__ $$g25, 29 (2023), 5476-5480$$pOrg. lett.$$tORGANIC LETTERS$$x1523-7060
000126945 8564_ $$s2784829$$uhttps://zaguan.unizar.es/record/126945/files/texto_completo.pdf$$yVersión publicada
000126945 8564_ $$s2784139$$uhttps://zaguan.unizar.es/record/126945/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000126945 909CO $$ooai:zaguan.unizar.es:126945$$particulos$$pdriver
000126945 951__ $$a2024-11-22-12:02:53
000126945 980__ $$aARTICLE