In the accompanying paper [Hemmerich, S., & Rosen, S.D. However, the mechanisms by which ADCs are internalized and activated remain unclear. Circumventing the steps of purification from native cell membranes, this methodology facilitates the reconstitution of membrane-associated proteins. We were able to bypass the salvage pathway by using an azide-functionalized analogue of GDP-fucose. Chen, Q., Zhang, D., Somorjai, G., Bertozzi, C. R. Carbohydrate sulfotransferases: mediators of extracellular communication, Chemoselective ligation reactions with proteins, oligosaccharides and cells, Inner space exploration: the chemical biologist's guide to the cell, Metabolic delivery of ketone groups to sialic acid residues - Application to cell surface glycoform engineering. Shon, D. J., Malaker, S. A., Pedram, K. n., Yang, E. n., Krishnan, V. n., Dorigo, O. n., Bertozzi, C. R. A Pragmatic Guide to Enrichment Strategies for Mass Spectrometry-Based Glycoproteomics. Chemical reactions that enable selective biomolecule labeling in living organisms offer a means to probe biological processes in vivo. In the past decade advances in genomics, proteomics and mass spectrometry have enabled the association of specific glycan structures with disease states. View details for Web of Science ID 000263320900008, View details for PubMedCentralID PMC2709987. During maturation, phagosomes containing engulfed particles fuse with various endosomal compartments through the action of regulatory molecules on the phagosomal membrane. Here, we report that metabolic cross-talk between the N-acetylgalactosamine salvage and O-GlcNAcylation pathways can be exploited for the tagging and identification of O-GlcNAcylated proteins. View details for Web of Science ID 000267049000011, View details for PubMedCentralID PMC2697281. To tackle this issue, we followed an unnatural sugar approach as bioorthogonal chemical reporters, where the use of azidosialyl residues allowed identifying the acquired sugar. We found that the fucose salvage pathway enzymes are expressed during zebrafish embryogenesis but that they process the azide-modified substrates inefficiently. Kamariza, M., Keyser, S. G., Utz, A., Knapp, B. D., Ealand, C., Ahn, G., Cambier, C. J., Chen, T., Kana, B., Huang, K. C., Bertozzi, C. R. Small RNAs are modified with N-glycans and displayed on the surface of living cells. In this work, we tested a panel of glycopolymers bearing a variety of lipids to identify those that persist on cell membranes. Glycans are attractive targets for molecular imaging but have been inaccessible because of their incompatibility with genetically encoded reporters. Seeliger, J. C., Topp, S., Sogi, K. M., Previti, M. L., Gallivan, J. P., Bertozzi, C. R. Thiacycloalkynes for Copper-Free Click Chemistry. View details for Web of Science ID 000435537701267. [27][28][29] This new field and technique allows researchers to chemically modify molecules in living organisms and not interrupt the processes of the cell. A recently developed technology, termed metabolic oligosaccharide engineering, enables glycan labeling with probes for visualization in cells and living animals, and enrichment of specific glycoconjugate types for proteomic analysis. View details for Web of Science ID 000077136900049, View details for Web of Science ID 000076649700013, View details for Web of Science ID 000075884200020. Specifically, weak bases with moderate activity against M. tuberculosis (fluoxetine, sertraline, and dibucaine) were shown to accumulate intracellularly due to differential permeability and relative abundance of their ionized and nonionized forms. Epithelial ovarian cancer (EOC) is a disease responsible for more deaths among women in the Western world than all other gynecologic malignancies. View details for Web of Science ID 000294081900008. Once introduced into target biomolecules, either metabolically or through chemical modification, the azide can be tagged with probes using one of three highly selective reactions: the Staudinger ligation, the Cu(I)-catalyzed azide-alkyne cycloaddition, or the strain-promoted [3 + 2] cycloaddition. The rv3406 strain did not replicate in minimal media with 2-ethyl hexyl sulfate as the sole sulfur source, in contrast to wild type Mtb or the complemented strain. View details for DOI 10.1016/j.celrep.2013.08.048, View details for Web of Science ID 000328263000025, View details for PubMedCentralID PMC3869705, View details for DOI 10.1371/journal.pone.0072304, View details for Web of Science ID 000323425700163. Physiological blood-brain transport is impaired with age by a shift in transcytosis. However, inside infected macrophages, bacteria encounter an environment which differs substantially from broth culture and are subject to important host-dependent pharmacokinetic phenomena which modulate drug activity. The quantitative changes in phagosomal proteins suggested a distinct role for mannose-capped LAM in modulating protein trafficking pathways that contribute to the arrest of phagosome maturation. Mucin biology has been difficult to study at the molecular level, in part, because methods to manipulate and structurally characterize mucin domains are lacking. Presented herein is the synthesis and evaluation of a bisubstrate analogue designed to inhibit estrogen sulfotransferase. Here, we report the identification of the SMK biosynthetic operon that, in addition to a previously identified sulfotransferase stf3, includes a putative cytochrome P450 gene (cyp128) and a gene of unknown function, rv2269c. We use a novel fractionation procedure to demonstrate that SL-1 is present on the cell surface, whereas SL(1278) is found exclusively in more internal layers. Azides installed within cell surface glycoconjugates by metabolism of a synthetic azidosugar were reacted with a biotinylated triarylphosphine to produce stable cell-surface adducts. These data highlight the power of advanced imaging methods to provide molecular and functional insights into glycocalyx biology. The sulfate esters on these structures are thought to be essential for high-affinity binding to L-selectin. The Cu(I)-catalyzed reaction was found to be most efficient for detecting azides in protein samples but was not compatible with live cells due to the toxicity of the reagents. Peptidoglycan (PG) is an essential component of the bacterial cell wall. After screening almost 8000 selected clones, we were able to isolate a single specific single chain Fv using two different selection strategies, one of which included elution with tyrosine sulfate. The participating functional groups must be inert to biological moieties, must selectively reactive with each other under biocompatible conditions, and, for in vivo applications, must be nontoxic to cells and organisms. A. Mineralization of synthetic polymer scaffolds: A bottom-up approach for the development of artificial bone, Mechanistic investigation of the Staudinger ligation. [10][11], Bertozzi was awarded the 2022 Nobel Prize in Chemistry, jointly with Morten P. Meldal and Karl Barry Sharpless, "for the development of click chemistry and bioorthogonal chemistry". Chemical tools have accelerated progress in glycoscience, reducing experimental barriers to studying protein glycosylation, the most widespread and complex form of posttranslational modification. Mechanistic and theoretical studies inspired the design of a series of cyclooctyne compounds bearing fluorine substituents, fused rings, and judiciously situated heteroatoms, with the goals of optimizing azide cycloaddition kinetics, stability, solubility, and pharmacokinetic properties. A., Cheng, E. H., Bertozzi, C. R., Boyce, M. Modulation of Ocular Surface Glycocalyx Barrier Function by a Galectin-3 N-terminal Deletion Mutant and Membrane-Anchored Synthetic Glycopolymers. The efficacy of these drugs is frequently undermined by acquired resistance. An unnatural derivative of N-acetyl-mannosamine, which has a ketone group, was converted to the corresponding sialic acid and incorporated into cell surface oligosaccharides metabolically, resulting in the cell surface display of ketone groups. Some of these techniques remove obstacles to glycoprotein synthesis by installing nonnative linkages and other modifications for facilitated assembly. Wojczyk, B. S., Stwora-Wojczyk, M. M., Hagen, F. K., Striepen, B., Hang, H. C., Bertozzi, C. R., Roos, D. S., Spitalnik, S. L. Metabolic oligosaccharide engineering as a tool for glycobiology, Formation of 1,1-alpha,alpha-glycosidic bonds by intramolecular aglycone delivery. We observed direct evidence for galectin-1-mediated extended cross-linking on the engineered cells, a phenomenon that was dependent on glycan structure. Circular dichroism of unglycosylated diptericin indicated that the peptide lacked structure both in plain buffer and in the presence of liposomes. O-GlcNAc transferase accepts UDP-GlcNAz as a nucleotide-sugar donor, appending an azidosugar onto its native substrates, which can then be detected by covalent labeling using azide-reactive chemical probes. Sialic acid is a major determinant of carbohydrate-receptor interactions in many systems pertinent to human health and disease. Although the sulfated xenobiotics bind poorly to the ER, both stimulated the growth of receptor-positive breast tumor cells. Ni bis(dithiolene) probes selectively labeled quadricyclane-modified bovine serum albumin, even in the presence of cell lysate. In our approach, the glycosyltransferase is separated into two domains, one that determines localization and one responsible for catalysis. The approach was validated by metabolic labeling of nuclear pore protein p62, which is known to be posttranslationally modified with O-GlcNAc. View details for Web of Science ID 000250428200015. These probes enable real-time imaging of trehalose mycolate biosynthesis and mycomembrane dynamics in the laboratory as well as in clinical settings for the detection of mycobacteria in patient samples. We found that E. coli's FGE-like activity is similarly promiscuous, enabling the use of novel aldehyde tag sequences for in vivo modification of recombinant proteins. The development of bioorthogonal reactions has classically focused on bond-forming ligation reactions. The above reactions, as well as several newcomers with bioorthogonal attributes, have enabled the high-precision chemical modification of biomolecules in vitro, as well as real-time visualization of molecules and processes in cells and live organisms. The first synthesis and characterization of [9]-, [12]-, and [18]cycloparaphenylene was demonstrated utilizing a novel aromatization reaction. View details for Web of Science ID 000266929900058, View details for PubMedCentralID PMC2812030, View details for Web of Science ID 000265985200026. The Staudinger ligation has sufficient biocompatibility for performance in living animals but suffers from phosphine oxidation and synthetic challenges. Here, we report an assay for mycobacterial strain assignment based on genetically conserved mycobacterial sulfatases. The azido sugars are then covalently tagged, either ex vivo or in vivo, using one of two azide-specific chemistries: the Staudinger ligation, or the strain-promoted [3+2] cycloaddition. Cotranslational modification of the proteins by FGE produced products bearing a unique aldehyde group. Furthermore, the same junctional peptidoglycan also serves as a mechanical link holding the daughter cells together and undergoes mechanical fracture during V snapping. View details for Web of Science ID 000169081700029. We devised an experimental model that mimics the structure of mycobacterial envelopes in which an immobile hydrophobic layer supports a TDM-rich, two-dimensionally fluid leaflet. The absence of activity on the trisaccharide Gal beta 1-->6Gal alpha-R indicates a requirement for a substrate with a terminal GlcNAc residue, suggesting that sulfation precedes further biosynthetic assembly of L-selection ligands. Because the parameters which govern this effect are well understood and are amenable to chemical modification, this knowledge may enable the rational development of more effective antibiotics against tuberculosis. Selective chemical reactions that are orthogonal to the diverse functionality of biological systems have become important tools in the field of chemical biology. Perrine, C. L., Ganguli, A., Wu, P., Bertozzi, C. R., Fritz, T. A., Raman, J., Tabak, L. A., Gerken, T. A. Polysialic acid governs T-cell development by regulating progenitor access to the thymus. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. Mutation of the N610 site prevented membrane-proximal N-glycosylation of CSF3R, which then drove ligand-independent cellular expansion. Application of the IsoTaG platform to 15 cell lines metabolically labeled with Ac4GalNAz or Ac4ManNAz revealed 1375 N- and 2159 O-glycopeptides, variously modified with 74 discrete glycan structures. The high signal-to-background ratio obtained using nanomolar concentrations of BARAC obviated the need for washing steps. Among her many honours are the Lemelson-MIT Prize (2010), the Arthur C. Cope Award of the American Chemical Society (2017), and the Wolf Prize in Chemistry (2022). The chemical reporter is then covalently modified in a highly selective fashion with an exogenously delivered probe. Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. The Leu-13 --> Gly (L13G) mutation is found in each of the three MetRS mutants, and the MetRS variant containing this single mutation is highly efficient in producing recombinant proteins that contain azidonorleucine. Moeckl, L., Pedram, K., Roy, A., Gustavsson, A., Bertozzi, C., Moerner, W. Glycopolymers for immune modulation in the tumor microenvironment, Computation-Guided Rational Design of a Peptide Motif That Reacts with Cyanobenzothiazoles via Internal Cysteine-Lysine Relay, Multiple Click-Selective tRNA Synthetases Expand Mammalian Cell-Specific Proteomics. Thus, this metabolic gene of an intracellular pathogen could have a secondary role in protection against the host immune response. Bioorthogonal chemical reactions are paving the way for new innovations in biology. View details for Web of Science ID A1997XK27100002. Furthermore, the palmitoylation of endogenous proteins including H- and N-Ras could be easily detected using omega-alkynyl-palmitate as label in cultured HeLa, Jurkat, and COS-7 cells, and, promisingly, in mice. We used this strategy to construct a paracrine signaling network in isolated 3-dimensional microtissues. Using comprehensive identification of RNA-binding proteins by mass spectrometry (ChIRP-MS), we took an RNA-centric viewpoint of flaviviral infection and identified several hundred proteins associated with both DENV and ZIKV genomic RNA in human cells. The inducible riboswitch platform has the potential to be a powerful general strategy for creating customized gene regulation systems in Mtb. Appel, M. J., Meier, K. K., Lafrance-Vanasse, J., Lim, H., Tsai, C., Hedman, B., Hodgson, K. O., Tainer, J. Elevated ROS resulted in reduced activity of cathepsin S and B, but not X, causing a proteolytic defect of MHC class II chaperone invariant chain Ii processing. Debets, M. F., Tastan, O. Y., Wisnovsky, S. P., Malaker, S. A., Angelis, N. n., Moeckl, L. K., Choi, J. n., Flynn, H. n., Wagner, L. J., Bineva-Todd, G. n., Antonopoulos, A. n., Cioce, A. n., Browne, W. M., Li, Z. n., Briggs, D. C., Douglas, H. L., Hess, G. T., Agbay, A. J., Roustan, C. n., Kjaer, S. n., Haslam, S. M., Snijders, A. P., Bassik, M. C., Moerner, W. E., Li, V. S., Bertozzi, C. R., Schumann, B. n. Delaveris, C. n., Wilk, A. n., Riley, N. n., Stark, J. n., Yang, S. n., Rogers, A. n., Ranganath, T. n., Nadeau, K. n., Blish, C. n., Bertozzi, C. n. Systematic discovery and functional interrogation of SARS-CoV-2 viral RNA-host protein interactions during infection. Mucin-type O-glycans could be imaged as early as 7 hours postfertilization, during the gastrula stage of development. Here, we show that increasing sialylated glycans on cancer cells inhibits human natural killer (NK) cell activation through the recruitment of sialic acid-binding immunoglobulin-like lectin 7 (Siglec-7). View details for DOI 10.1073/pnas.0912081107, View details for Web of Science ID 000278549300009, View details for PubMedCentralID PMC2890823. Preliminary screening has identified compounds that inhibit estrogen sulfotransferase (EST), an enzyme relevant to breast cancer. The development of rapid screening methods for probing glycosyltransferase activities is essential for advancing the field of glycobiology. These improvements represent a lowering of the limit of detection in the RASC-2 platform to 0.9 Mtb bacilli per 100L of exhaled air from 3.3 Mtb bacilli per 100L (RASC-1).This study demonstrates that technical improvements in particle collection together with sensitive detection enable rapid quantitation of viable Mtb in bioaerosols of sputum positive TB cases. Shin, S., Comolli, L. R., Tscheliessnig, R., Wang, C., Ki Tae Nam, K. T., Hexemer, A., Siegerist, C. E., De Yoreo, J. J., Bertozzi, C. R. D-Amino Acid Chemical Reporters Reveal Peptidoglycan Dynamics of an Intracellular Pathogen. We developed a multiplex analysis platform based on antibody detection by agglutination-PCR (ADAP) for the sample-sparing measurement of GAD, IA-2 and insulin autoantibodies/antibodies in 1 muL serum. View details for DOI 10.1074/jbc.M304928200, View details for Web of Science ID 000185713800121. Kumar, P., Schelle, M. W., Jain, M., Lin, F. L., Petzold, C. J., Leavell, M. D., Leary, J. The cysH mutant caused disease and death after 4-7 weeks of infection in four different groups of mice - Rag1(-/-), NOS2(-/-), gp91phox(-/-) NOS2(-/-) and gp91phox(-/-) mice given aminoguanidine [to suppress the effects of nitric oxide synthase 2 (NOS2)]- indicating minimal metabolic effect on the cysH mutant survival in these mice. Cyclooctyne reagents have now been used for labeling azide-modified biomolecules on cultured cells and in live Caenorhabditis elegans, zebrafish, and mice. In addition, we have redefined the substrate specificity of the B. subtilis CysH, formerly designated a PAPS reductase, as an APS reductase, based on its ability to complement a mutant E. coli strain deficient in APS kinase. Fusion of these domains to the proteins FRB and FKBP enabled their induced assembly by the natural product rapamycin. This study reports the vaccine potential of an attenuated 5'-adenosine phosphosulfate reductase mutant (DeltacysH) of M. tuberculosis. Jacobs, C. L., Goon, S., Yarema, K. J., Hinderlich, S., Hang, H. C., Chai, D. H., Bertozzi, C. R. Biosynthesis of sialylated lipooligosaccharides in Haemophilis ducreyi is dependent on exogenous sialic acid and not mannosamine. These results establish the foundation for further development of BPDA-based colorimetric sensors. The active cuprous FGE complex was interrogated directly by X-ray absorption spectroscopy. To verify incorporation of the nonnatural sugars at N-glycan core positions, endoglycosidase H (endoH)-digested peptides from a purified secretory glycoprotein, Ygp1, were analyzed by mass spectrometry. In addition to carrying out a pivotal role in parasite persistence/replication within the infected mammal, the trans-sialidase is shed into the bloodstream and induces alterations in the host immune system by modifying the sialylation of the immune cells. In vivo, BPA appears to have greater activity than is suggested by its estrogen receptor (ER) binding affinity. [reaction: see text]. B cell glycoproteins were robustly labeled with GalNAz but T cell glycoproteins were not, suggesting fundamental differences in glycosylation machinery or metabolism. OliLux Biosciences develops new methods for tuberculosis detection. Taken together, this method offers a potentially powerful new chemical tool for studying simultaneous oxidative stress and inflammation processes in living animals during injury, aging, and disease, as well as a versatile approach for concurrent monitoring of multiple analytes using luciferin-based bioluminescence imaging technologies. View details for Web of Science ID 000172181700022. [2] As of 2022, 12 awardees have subsequently become Nobel laureates; the most recent of those is Carolyn Bertozzi, who received the Nobel Prize the same year. A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-N-acetylgalactosamine (GalNAc) residue. The leukocyte adhesion molecule L-selection participates in the initial attachment of blood-borne lymphocytes to high endothelial venules (HEVs) during lymphocyte homing to secondary lymphoid organs, and contributes to leukocyte adhesion and extravasation in HEV-like vessels at sites of chronic inflammation. That inhibit estrogen sulfotransferase and disease installed within cell surface glycoconjugates by of... Vivo, BPA appears to have greater activity than is suggested by its receptor. A. Mineralization of synthetic polymer scaffolds: a bottom-up approach for the of. 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