215654-55-0Relevant articles and documents
Aldehyde-mediated bioconjugation: Via in situ generated ylides
Parmar, Sangeeta,Pawar, Sharad P.,Iyer, Ramkumar,Kalia, Dimpy
supporting information, p. 14926 - 14929 (2019/12/24)
A technically simple approach for rapid, high-yielding and site-selective bioconjugation has been developed for both in vitro and cellular applications. This method involves the generation of maleimido-phosphonium ylides via 4-nitrophenol catalysis under physiological conditions followed by their Wittig reactions with aldehyde-appended biomolecules.
Stable and Rapid Thiol Bioconjugation by Light-Triggered Thiomaleimide Ring Hydrolysis
Kalia, Dimpy,Pawar, Sharad P.,Thopate, Jyoti S.
supporting information, p. 1885 - 1889 (2017/02/05)
Maleimide-mediated thiol-specific derivatization of biomolecules is one of the most efficacious bioconjugation approaches currently available. Alarmingly, however, recent work demonstrates that the resulting thiomaleimide conjugates are susceptible to breakdown via thiol exchange reactions. Herein, we report a new class of maleimides, namely o-CH2NHiPr phenyl maleimides, that undergo unprecedentedly rapid ring hydrolysis after thiol conjugation to form stable thiol exchange-resistant conjugates. Furthermore, we overcome the problem of low shelf lives of maleimide reagents owing to their propensity to undergo ring hydrolysis prior to bioconjugation by developing a photocaged version of this scaffold that resists ring hydrolysis. UV irradiation of thiol bioconjugates formed with this photocaged maleimide unleashes rapid thiomaleimide ring hydrolysis to yield the desired stable conjugates within 1 h under gentle, ice-cold conditions.
Thiol-reactive Fluorescent probes for Protein Labelling
Corrie, John E. T.
, p. 2975 - 2982 (2007/10/02)
Cyclisation of N-alkylmaleic acids mediated by acetic anhydride in dimethylacetamide in the presence of traces of cobalt naphthenate has been used for efficient assembly of a range of fluorescent maleimide reagents.The fluorescence responses of these reagents to addition of thiol across the maleimide double bond, and to hydrolysis of the meleimide ring, are described.
