She coined the term bioorthogonal chemistry to describe the use of click reactionsquick, simple chemical reactionsto study living cells. Mougous, J. D., Lee, D. H., Hubbard, S. C., Schelle, M. W., Vocadlo, D. J., Berger, J. M., Bertozzi, C. R. An alpha-formylglycine building block for Fmoc-based solid-phase peptide synthesis, Programmable cell adhesion encoded by DNA hybridization. We apply the strategy to a particularly redundant yet disease-relevant human glycosyltransferase family, the polypeptide N-acetylgalactosaminyl transferases. To validate our results, we employed gel shift assays based on conjugating mass tags to O-GlcNAc groups. Atoms out of Blobs: CryoEM Takes the Nobel Prize in Chemistry. Cortez, F. d., Gebhart, D., Robinson, P. V., Seftel, D., Pourmandi, N., Owyoung, J., Bertozzi, C. R., Wilson, D. M., Maahs, D. M., Buckingham, B. Both normal and cancerous prostate tissues were sliced and cultured in the presence of the azide-functionalized sialic acid biosynthetic precursor Ac4 ManNAz. IsoTaG is therefore an effective platform for identification of intact glycopeptides labeled by alkynyl or azido sugars and will facilitate further studies of the glycoproteome. 275, 21075-21080). The expression of recombinant M. tuberculosis APS kinase provides a means for the discovery of inhibitors of this enzyme and thus of the biosynthesis of SL-1. IsoTaG is therefore positioned to enhance structural understanding of the glycoproteome. Cambier, C. J., Banik, S. M., Buonomo, J. Mass spectrometry revealed that the N610 residue is part of a consensus N-linked glycosylation motif in the receptor, usually linked to complex glycans. Carroll, K. S., Gao, H., Chen, H. Y., Leary, J. This heterogeneity precludes enrichment strategies that can be universally beneficial for all glycan classes. Likewise, these crosslinking probes serve as ideal chemical tools for structural studies between NRPS modules where functional assays are lacking. We observed direct evidence for galectin-1-mediated extended cross-linking on the engineered cells, a phenomenon that was dependent on glycan structure. The azido sugars are then covalently tagged with imaging probes or epitope tags, either ex vivo or in vivo, using an azide-specific reaction. Here, we report the development of a nanoscale cell injection system (termed the nanoinjector) that uses carbon nanotubes to deliver cargo into cells. The end purpose of the described approaches is the production of glycosylated materials for experiments relevant to the biological investigation of glycoproteins, although the strategies presented apply to other posttranslational modifications as well. The approach provides a means for studying sulfate-dependent processes in cellular systems and, potentially, in vivo. Mucin-type O-glycans could be imaged as early as 7 hours postfertilization, during the gastrula stage of development. The GPI-protein analogs also diffused freely in cellular membranes. This structure suggests a molecular mechanism by which conserved G domain architecture is used to energetically link GTP turnover to the production of an essential metabolite. Finally, mechanistic and structural data from sulfate-assimilation enzymes have revealed how M. tb controls the flux of sulfate in the cell. Cotranslational modification of the proteins by FGE produced products bearing a unique aldehyde group. Rabuka, D., Rush, J. S., dehart, G. W., Wu, P., Bertozzi, C. R. Cellular Microfabrication: Observing Intercellular Interactions Using Lithographically-Defined DNA Capture Sequences. View details for Web of Science ID 000177054900001, View details for Web of Science ID 000175790100030, Here we report a concise stereoselective synthesis of myo-inositol via ring-closing metathesis. Deacetylated sialic acids modulates immune mediated cytotoxicity via the sialic acid-Siglec pathway. Shon, D., Malaker, S. A., Pedram, K., Yang, E., Krishnan, V., Dorigo, O., Bertozzi, C. R. On-tissue microscale glycoproteomics and N-glycan imaging reveal global dysregulation of canine glioma glycoproteomic landscape. Comparison of these data to images of wild-type SbpA layers on intact cells gave insight into the interactions responsible for bilayer formation. Baskin, J. M., Prescher, J. View details for Web of Science ID 000252686400026, View details for PubMedCentralID PMC2735189, View details for DOI 10.1002/anie.200705363, View details for Web of Science ID 000257427000014, View details for PubMedCentralID PMC2847391. Rodriguez, E. C., Winans, K. A., King, D. S., Bertozzi, C. R. Engineered cell surfaces: Fertile ground for molecular landscaping, Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis. Kumar, P., Schelle, M. W., Jain, M., Lin, F. L., Petzold, C. J., Leavell, M. D., Leary, J. WebBertozzi is a professor of Humanities and Sciences, and of Chemical and Systems Biology and of Radiology. This "bounce-back" response is achieved through a unique mechanism. Grand Challenges in Chemistry for 2016 and Beyond. Other sulfonucleotide reductases from structurally divergent subclasses appear to use the same mechanism, suggesting that this family of enzymes has evolved from a common ancestor. Disruption of papA2 and papA1 in M. tuberculosis confirmed their essential role in SL-1 biosynthesis and their order of action. Moreover, approximately 1.3 microM total exogenous sialic acid was sufficient to obtain about 50% of the maximum production of sialic acid-containing glycoforms observed under in vitro growth conditions. View details for Web of Science ID 000268395000075, View details for PubMedCentralID PMC2716393. Electron-based dissociation methods are necessary to capture the O-glycopeptide diversity present in OpeRATOR digestions. The structure, high-resolution Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry, and quantitative kinetic analysis, establish that the two chemically discrete steps of the overall reaction take place at distinct sites on the enzyme, mediated via conformational flexibility of the C-terminal 18 residues. Transposon-sequencing was then used to define its essential gene set and identify loci that, when inactivated, confer hypersensitivity to ethambutol (EMB), a drug that targets AG biogenesis. Kehoe, J. W., Velappan, N., Walbolt, M., Rasmussen, J., King, D., Lou, J., Knopp, K., Pavlik, P., Marks, J. D., Bertozzi, C. R., Bradbury, A. R. Substrate recognition, protein dynamics, and iron-sulfur cluster in Pseudomonas aeruginosa adenosine 5 '-phosphosulfate reductase. Swarts, B. M., Holsclaw, C. M., Jewett, J. C., Alber, M., Fox, D. M., Siegrist, M. S., Leary, J. Stowell, C. L., Barvian, K. K., Young, P. C., Bigsby, R. M., Verdugo, D. E., Bertozzi, C. R., Widlanski, T. S. Discovery of aminoacyl-tRNA synthetase activity through cell-surface display of noncanonical amino acids. In recent years, an alternative tool for tagging biomolecules has emerged from the chemical biology community--the bioorthogonal chemical reporter. Polysialyltransferases catalyze the glycosylation of the neural cell adhesion molecule (NCAM) with polysialic acid (PSA). In addition, Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry was employed to detect the noncovalent complexes, the Stf0-PAPS and Stf0-trehalose binary complexes, and a Stf0-3'-phosphoadenosine 5'-phosphate-trehalose ternary complex. Schumann, B., Debets, M., Wisnovsky, S., Agbay, A., Wagner, L., Choi, J., Gray, M., Bertozzi, C. Quantitative super-resolution microscopy reveals the architecture of the mammalian glycocalyx and its changes during cancer progression. Our observations are the first reported instance of dehydration resistance provided by a membrane glycolipid. Her research group profiles changes in cell surface glycosylation associated with cancer, inflammation and bacterial infection, and uses this information to develop new diagnostic and therapeutic approaches, most recently in the area of immuno-oncology. We discuss the use of fluorescent and fluorogenic trehalose probes for the detection of the mycobacterial trehalose glycolipids. CysQ is a 3'-phosphoadenosine-5'-phosphatase that dephosphorylates intermediates from the sulfate assimilation pathway of Mycobacterium tuberculosis (Mtb). Parak, W. J., Gerion, D., Zanchet, D., Woerz, A. S., Pellegrino, T., Micheel, C., Williams, S. C., Seitz, M., Bruehl, R. E., Bryant, Z., Bustamante, C., Bertozzi, C. R., Alivisatos, A. P. Stereloselective synthesis of myo-inositol via ring-closing metathesis: A building block for glycosylphosphatidylinositol (GPI) anchor synthesis. They write new content and verify and edit content received from contributors. Myoblast cells were patterned with high efficiency and remained undifferentiated after surface attachment. View details for DOI 10.1021/jacs.0c07700. View details for DOI 10.1016/j.biomaterials.2004.01.025, View details for Web of Science ID 000222040300008, View details for DOI 10.1002/cbic.200400156, View details for Web of Science ID 000224453500014. View details for DOI 10.1002/anie.201504249, View details for DOI 10.1021/jacs.5b04279, View details for Web of Science ID 000360321100003, View details for DOI 10.1021/acscentsci.5b00275, View details for PubMedCentralID PMC4827550. WebBio. Nrf1 is constitutively translocated into the ER lumen, N-glycosylated, and then targeted for proteasomal degradation via the ER-associated degradation (ERAD) pathway. The key building block was a 2-azido-3-thiogalactose-Thr analogue that was incorporated into a peptide by fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Paszek, M. J., DuFort, C. C., Rossier, O., Bainer, R., Mouw, J. K., Godula, K., Hudak, J. E., Lakins, J. N., Wijekoon, A. C., Cassereau, L., Rubashkin, M. G., Magbanua, M. J., Thorn, K. S., Davidson, M. W., Rugo, H. S., Park, J. W., Hammer, D. A., Giannone, G., Bertozzi, C. R., Weaver, V. M. Imaging bacterial peptidoglycan with near-infrared fluorogenic azide probes. Marcaurelle, L. A., Rodriguez, E. C., Bertozzi, C. R. Direct incorporation of unprotected ketone groups into peptides during solid-phase synthesis: Application to the one-step modification of peptides with two different biophysical probes for FRET, Identification of an N-acetylglucosamine-6-O-sulfotransferase activity specific to lymphoid tissue: an enzyme with a possible role in lymphocyte homing. Developmental events can be monitored at the cellular and molecular levels by using noninvasive imaging techniques. Carolyn earned Appel, M. J., Meier, K. K., Lafrance-Vanasse, J., Lim, H., Tsai, C., Hedman, B., Hodgson, K. O., Tainer, J. Thus, cell assembly can be highly controlled, enabling the design of microtissues with defined cell composition and stoichiometry. Armstrong, J. I., Portley, A. R., Chang, Y. T., Nierengarten, D. M., Cook, B. N., Bowman, K. G., Bishop, A., Gray, N. S., Shokat, K. M., Schultz, P. G., Bertozzi, C. R. Metabolic labeling of glycoproteins with chemical tags through unnatural sialic acid biosynthesis. However, little is known about how alterations in O-GlcNAc cycling affect human embryonic stem cell (hESC) neural differentiation. A key tool we developed for this study is a cell-permeable, small molecule inhibitor of GlcNAc 2-epimerase designed based on mechanistic principles. Sequential assembly of the septal cell envelope prior to V snapping in Corynebacterium glutamicum. One such glycolipid, Sulfolipid-1 (SL-1), consists of a trehalose-2-sulfate (T2S) core acylated with four lipid moieties. the glycome, has garnered significant attention from chemists and biologists alike. Unnatural sialic acids are generated by metabolic conversion of synthetic N-acyl mannosamines and are typically incorporated into cell-surface glycoconjugates. In vivo molecular imaging holds promise for understanding the underlying mechanisms of health, injury, aging, and disease, as it can detect distinct biochemical processes such as enzymatic activity, reactive small-molecule fluxes, or post-translational modifications. Mycobacterium tuberculosis (M. tuberculosis) is an intracellular pathogen possessing a complex mixture of cell wall lipids that are thought to modulate the activities of host macrophages. Our study supports an essential role of one of the GalNAc-Ts - GALNT3, in EOC dissemination, including its implication in modulating PTMs and EOC metabolism. The efficacy of antimicrobial drugs against Mycobacterium tuberculosis, an intracellular bacterial pathogen, is generally first established by testing compounds against bacteria in axenic culture. ScTyrY43G and MmPheT413G label overlapping but distinct proteomes in human cell lines, with broader proteome coverage upon their coexpression. Thus, choice of enrichment strategy has profoundimplications on experimental outcomes. Malaker, S. A., Quanico, J., Raffo-Romero, A., Kobeissy, F., Aboulouard, S., Tierny, D., Bertozzi, C. R., Fournier, I., Salzet, M. The CD22-IGF2R interaction is a therapeutic target for microglial lysosome dysfunction in Niemann-Pick type C. Pluvinage, J. V., Sun, J., Claes, C., Flynn, R. A., Haney, M. S., Iram, T., Meng, X., Lindemann, R., Riley, N. M., Danhash, E., Chadarevian, J. P., Tapp, E., Gate, D., Kondapavulur, S., Cobos, I., Chetty, S., Paca, A. M., Paca, S. P., Berry-Kravis, E., Bertozzi, C. R., Blurton-Jones, M., Wyss-Coray, T. An enzymatic toolkit for selective proteolysis, detection, and visualization of mucin-domain glycoproteins. A., Baskin, J. M., Bertozzi, C. R., Koberstein, J. T., Turro, N. J. However, what is lacking from this biochemical picture is how cells, tissues, and organisms interpret glycan patterns and translate this information into appropriate responses. The isolation of this antibody signals the potential of phage antibody libraries in the derivation of reagents specific for post-translational modifications, although the extensive screening required indicates that such antibodies are extremely rare. This story was updated on Wednesday, Oct. 6, at 1:23 p.m. PDT. Site-directed mutagenesis of any cysteine residue within the conserved motif led to a loss of cluster with a concomitant loss in catalytic activity, while secondary structure was preserved. Lectins, glycan-binding proteins, are thought to bridge this gap by decoding the glycome and dictating cell fate based on the underlying chemical identities and properties of the glycome. The resulting trehalose biosynthesis mutant was unable to proliferate and enter stationary phase unless supplemented with trehalose. Synthetic oligosaccharides and glycoconjugates provide materials for correlating structure with function. Douglas, E. S., Chandra, R. A., Bertozzi, C. R., Mathies, R. A., Francis, M. B. Metabolic labeling of glycans with azido sugars and subsequent glycan-profiling and visualization via Staudinger ligation, Synthetic glycobiology: exploits in the Golgi compartment, Using phage display to select antibodies recognizing post-translational modifications independently of sequence context. Dai, T. n., Xie, J. n., Zhu, Q. n., Kamariza, M. n., Jiang, K. n., Bertozzi, C. R., Rao, J. n. Optimal Dissociation Methods Differ for N- and O-glycopeptides. We further generated rapamycin-inducible chimeric enzymes comprising the localization domain of a sulfotransferase and the catalytic domain of a glycosyltransferase, demonstrating the generality of the system among other Golgi enzymes. A., Bertozzi, C. R. Synthesis of mono- and dideoxygenated alpha,alpha-trehalose analogs. The high signal-to-background ratio obtained using nanomolar concentrations of BARAC obviated the need for washing steps. The ability to generate chemically defined analogues of GPI-anchored proteins is an important step toward elucidating the molecular functions of this interesting post-translational modification. This approach led to the identification of 2,219 intact O-linked glycopeptides across 1,045 glycoproteins. A., Rajaiah, G., Falck, J. R., Bertozzi, C. R., Berthiaume, L. G. Identification of palmitoylated mitochondrial proteins using a bio-orthogonal azido-palmitate analogue. Such genetic engineering in combination with stable isotopic labeling can be applied to various metabolic pathways and their products. View details for DOI 10.1073/pnas.1010045108, View details for Web of Science ID 000287580400017. Chemistry Professor Carolyn Bertozzi has been named the Baker Family Director of Stanford ChEMH, an interdisciplinary research institute launched in 2013 to bridge chemistry, engineering and medicine to improve human health. This antibody was able to recognize sulfotyrosine independently of its sequence context in test peptides and a number of different natural proteins. View details for DOI 10.1002/anie.200805756, View details for Web of Science ID 000267713800017, View details for PubMedCentralID PMC2735190. Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. Lantos, A. For her groundbreaking contributions to click chemistry and bioorthogonal chemistry, Bertozzi was awarded the 2022 Nobel Prize for Chemistry, which she shared with American chemist K. Barry Sharpless and Danish chemist Morten P. Meldal. Chen, X., Lee, G. S., Zettl, A., Bertozzi, C. R. Functional glass slides for in vitro evaluation of interactions between osteosarcoma TE85 cells and mineral-binding ligands. An intriguing example is Sulfolipid-1 (SL-1), a sulfated glycolipid that has been implicated in Mtb pathogenesis, although no direct role for SL-1 in virulence has been established. These findings functionally link mucinous proteins with tumor aggression, and offer a new view of the cancer glycocalyx as a major driver of disease progression. 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 PubMedCentralID PMC5842139. Mougous, J. D., Leavell, M. D., Senaratne, R. H., Leigh, C. D., Williams, S. J., Riley, L. W., Leary, J. 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. Into the interactions responsible for bilayer formation SL-1 ), consists of a consensus N-linked glycosylation motif in the.! Inhibitor of GlcNAc 2-epimerase designed based on mechanistic principles N-linked glycosylation motif the! Between NRPS modules where functional assays are lacking molecule ( NCAM ) with polysialic acid ( PSA ) study! 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