67917-51-5Relevant academic research and scientific papers
General method for the preparation of active esters by palladium-catalyzed alkoxycarbonylation of aryl bromides
De Almeida, Angelina M.,Andersen, Thomas L.,Lindhardt, Anders T.,De Almeida, Mauro V.,Skrydstrup, Troels
supporting information, p. 1920 - 1928 (2015/02/19)
A useful method was developed for the synthesis of active esters by palladium-catalyzed alkoxycarbonylation of (hetero)aromatic bromides. The protocol was general for a range of oxygen nucleophiles including N-hydroxysuccinimide (NHS), pentafluorophenol (PFP), hexafluoroisopropyl alcohol (HFP), 4-nitrophenol, and N-hydroxyphthalimide. A high functional group tolerance was displayed, and several active esters were prepared with good to excellent isolated yields. The protocol was extended to access an important synthetic precursor to the HIV-protease inhibitor, saquinavir, by formation of an NHS ester followed by acyl substitution.
Primary arylamine-based tyrosine-targeted protein modification
Wang, Lin,Gruzdys, Valentinas,Pang, Nan,Meng, Fanhao,Sun, Xue-Long
, p. 39446 - 39452 (2014/12/09)
Tyrosine-targeted modification is of great interest in the site-specific protein modification applications. Aniline derivatives are attractive molecules for tyrosine-targeted protein modifications through either diazonium coupling or three-component Mannich type reactions. In this report, with BSA as a model protein, primary arylamines were demonstrated to incorporate bioorthogonal azide functionality for further site-specific protein modification via click chemistry, glycans for glyco-engineering, and PEG chains for PEGylation to the protein via tyrosine-targeted modification. The successful primary arylamine-based BSA modifications were confirmed by SDS-PAGE, western blot, and MALDI-TOF mass spectrometry. In comparison, three-component Mannich type reaction affords much higher reaction yields than diazonium coupling reaction in all modifications. Further, this study confirmed the importance of the electron withdrawing substituent on the para position of the phenyl ring for the tyrosine-targeted diazonium coupling reaction.
