2887-07-2Relevant articles and documents
Pd(II)-Mediated C?H Activation for Cysteine Bioconjugation
Tilden, James A. R.,Lubben, Anneke T.,Reeksting, Shaun B.,Kociok-K?hn, Gabriele,Frost, Christopher G.
supporting information, (2022/01/19)
Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition-metal mediated bioconjugation chemistry involves the use of Pd(II) complexes prepared via an oxidative addition process. Herein, the preparation of Pd(II) complexes for cysteine bioconjugation via a facile C?H activation process is reported. These complexes show bioconjugation efficiency competitive with what is seen in the current literature, with a user-friendly synthesis, common Pd(II) sources, and a more cost-effective ligand. Furthermore, these complexes need not be isolated, and still achieve high conversion efficiency and selectivity of a model peptide. These complexes also demonstrate the ability to selectively arylate a single surface cysteine residue on a model protein substrate, further demonstrating their utility.
Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar-Based Molecules that Target Bacterial Glucosyltransferase
Hartman, Alwin M.,Jumde, Varsha R.,Elgaher, Walid A. M.,Te Poele, Evelien M.,Dijkhuizen, Lubbert,Hirsch, Anna K. H.
, p. 113 - 123 (2020/07/13)
We applied dynamic combinatorial chemistry (DCC) to find novel ligands of the bacterial virulence factor glucosyltransferase (GTF) 180. GTFs are the major producers of extracellular polysaccharides, which are important factors in the initiation and development of cariogenic dental biofilms. Following a structure-based strategy, we designed a series of 36 glucose- and maltose-based acylhydrazones as substrate mimics. Synthesis of the required mono- and disaccharide-based aldehydes set the stage for DCC experiments. Analysis of the dynamic combinatorial libraries (DCLs) by UPLC-MS revealed major amplification of four compounds in the presence of GTF180. Moreover, we found that derivatives of the glucose-acceptor maltose at the C1-hydroxy group act as glucose-donors and are cleaved by GTF180. The synthesized hits display medium to low binding affinity (KD values of 0.4–10.0 mm) according to surface plasmon resonance. In addition, they were investigated for inhibitory activity in GTF-activity assays. The early-stage DCC study reveals that careful design of DCLs opens up easy access to a broad class of novel compounds that can be developed further as potential inhibitors.
Fluorescent probe for rapidly detecting β - galactosidase and preparation method and application thereof
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Paragraph 0047; 0051-0053, (2021/10/27)
The invention relates to a fluorescent probe for rapidly detecting β - galactosidase and a preparation method and application thereof. The fluorescent probe for rapidly detecting β - galactosidase has a chemical structural formula as shown in (I). The nea