19878-26-3Relevant articles and documents
Combining Orthogonal Chain-End Deprotections and Thiol–Maleimide Michael Coupling: Engineering Discrete Oligomers by an Iterative Growth Strategy
Huang, Zhihao,Zhao, Junfei,Wang, Zimu,Meng, Fanying,Ding, Kunshan,Pan, Xiangqiang,Zhou, Nianchen,Li, Xiaopeng,Zhang, Zhengbiao,Zhu, Xiulin
, p. 13612 - 13617 (2017)
Orthogonal maleimide and thiol deprotections were combined with thiol–maleimide coupling to synthesize discrete oligomers/macromolecules on a gram scale with molecular weights up to 27.4 kDa (128mer, 7.9 g) using an iterative exponential growth strategy with a degree of polymerization (DP) of 2n?1. Using the same chemistry, a “readable” sequence-defined oligomer and a discrete cyclic topology were also created. Furthermore, uniform dendrons were fabricated using sequential growth (DP=2n?1) or double exponential dendrimer growth approaches (DP=2 22n ?1) with significantly accelerated growth rates. A versatile, efficient, and metal-free method for construction of discrete oligomers with tailored structures and a high growth rate would greatly facilitate research into the structure–property relationships of sophisticated polymeric materials.
Erratum: Direct cytosolic delivery of proteins through coengineering of proteins and polymeric delivery vehicles (Journal of the American Chemical Society (2020) 142:9 (4349-4355) DOI: 10.1021/jacs.9b12759)
Clark, Vincent,Elia, James,Gopalakrishnan, Sanjana,Goswami, Ritabrita,Jeon, Taewon,Lee, Yi-Wei,Luther, David C.,Rotello, Vincent M.
, p. 6702 - 6702 (2021)
In this revised Supporting Information file, Figure S15 was misplaced in the text. The corrected figure is shown in the corrected Supporting Information file. This change does not affect any conclusions of the article, but this correction of the record is important.
A retro-Diels-Alder reaction to uncover maleimide-modified surfaces on monolayer-protected nanoparticles for reversible covalent assembly
Zhu, Jun,Kell, Arnold J.,Workentin, Mark S.
, p. 4993 - 4996 (2006)
(Chemical Equation Presented) Maleimide-modified monolayer-protected gold nanoparticles (MPGN) are prepared from the protected furan-maleimide via the thermally reversible Diels-Adler reaction when required. These maleimide-MPGNs serve as a general platform allowing for a Diels-Alder reaction with furan-modified MPN to prepare larger 3D networks reversibly.
Inverse electron-demand Diels-Alder (iEDDA) bioorthogonal conjugation of half-sandwich transition metallocarbonyl entities to a model protein
Fischer-Durand, Nathalie,Jamroz, Daria,Jarzyński, Szymon,Palusiak, Marcin,Rudolf, Bogna,Salmain, Michèle,St?pniewska, Marlena,Wojtulewski, S?awomir
, (2020)
Novel transition metallocarbonyl complexes carrying a norbornene or an oxanorbornene group were synthesized by [4 + 2] cycloaddition between the organometallic maleimide dienophiles and cyclopentadiene or furan, respectively. The oxanorbornene adduct was obtained as a mixture of endo and exo isomers as confirmed by X-ray diffraction and NMR spectroscopy. The (oxa)norbornene groups further provided convenient chemical reporters to carry out inverse electron demand Diels-Alder (iEDDA) reactions with tetrazine derivatives. Detailed kinetic studies with a model tetrazine revealed that faster rates of reaction were determined with both isomers of the oxanorbornene complex with respect to the norbornene complexes. Eventually, incorporation of metallocarbonyl entities into bovine serum albumin equipped with tetrazine handles was achieved as shown by IR spectroscopy of the protein conjugates.
Controlling RNA digestion by RNase H with a light-activated DNA hairpin
Tang, Xinjing,Dmochowski, Ivan J.
, p. 3523 - 3526 (2006)
(Figure Presented) Making sense: A DNA hairpin was synthesized by attaching a 20-mer antisense oligodeoxynucleotide (asODN) to a sense ODN through a bifunctional photocleavable linker. This conjugate became much less stable upon UV photoactivation (ΔTsub
Self-Complementary ABC Triblock Copolymers via Ring-Opening Metathesis Polymerization
Bazzi, Hassan S.,Bouffard, Jean,Sleiman, Hanadi F.
, p. 7899 - 7902 (2003)
The synthesis of self-complementary triblock copolymers using controlled ring-opening metathesis polymerization was presented. It was shown that polymers possess ordered sequences of complementary molecular recognition blocks and could be synthesized efficiently. It was found that changing the triblock copolymer sequence resulted in materials with different self-assembly properties.
Experimental and theoretical studies of selective thiol-ene and thiol-yne click reactions involving N -substituted maleimides
Stolz, Robert M.,Northrop, Brian H.
, p. 8105 - 8116 (2013)
A combination of experimental and computational methods has been used to understand the reactivity and selectivity of orthogonal thiol-ene and thiol-yne ″click″ reactions involving N-allyl maleimide (1) and N-propargyl maleimide (2). Representative thiols methyl-3-mercaptopropionate and β-mercaptoethanol are shown to add exclusively and quantitatively to the electron poor maleimide alkene of 1 and 2 under base (Et3N) initiated thiol-Michael conditions. Subsequent radical-mediated thiol-ene or thiol-yne reactions can be carried out to further functionalize the remaining allyl or propargyl moieties in near quantitative yields (>95%). Selectivity, however, can only be achieved when base-initiated thiol-Michael reactions are carried out first, as radical-mediated reactions between equimolar amounts of thiol and N-substituted maleimides give complex mixtures of products. CBS-QB3 calculations have been used to investigate the energetics and kinetics of reactions between a representative thiol (methyl mercaptan) with N-allyl and N-propargyl maleimide under both base-initiated and radical-mediated conditions. Calculations help elucidate the factors that underlie the selective base-initiated and nonselective radical-mediated thiol-ene/yne reactions. The results provide additional insights into how to design selective radical-mediated thiol-ene/yne reactions.
Aiming at the tumor-specific accumulation of MGMT-inhibitors: First description of a synthetic strategy towards inhibitor-peptide conjugates
W?ngler, Bj?rn,Schirrmacher, Ralf,W?ngler, Carmen
, (2020)
In the therapy of cancer, alkylating agents are an efficient and often-used substance class. However, cells can repair the resulting alkyl modifications in the O6-position of guanine using the repair protein methylguanine methyltransferase (MGM
An array-based nanosensor for detecting cellular responses in macrophages induced by femtomolar levels of pesticides
Chattopadhyay, Aritra Nath,Geng, Yingying,Jiang, Mingdi,Rotello, Vincent M.
supporting information, p. 2890 - 2893 (2022/03/09)
Environmental agents can induce cellular responses at concentrations far below the limits of detection for current viability and biomarker-based cell sensing platforms. Hypothesis-free cell sensor platforms can be engineered to maximize sensitivity to phenotypic changes, providing a tool for lowering the threshold for detecting cellular changes. Pesticides are one of the most prevalent sources of chemical exposure due to their use in food and agriculture fields. We report here a FRET-based nanosensor array engineered to maximize responses to changes at cell surfaces after pesticide exposure. This sensor array robustly detected macrophage responses to femtomolar concentrations of common pesticides-orders of magnitude lower concentrations than traditional toxicological and biomarker-based strategies. Significantly, this platform was able to classify these responses by pesticide class, demonstrating the ability to distinguish between changes induced by these different agents. Taken together, hypothesis-free cell surface sensing is a promising tool for detecting the effects of ultra-trace environmental chemicals on human health, as well as detecting threshold responses for use in drug discovery and diagnostics.
