View details for Web of Science ID 000178916000019. Metabolic labeling of recombinant interferon-beta and GlyCAM-Ig was achieved, demonstrating the utility of the method for functionalizing N-linked and O-linked glycoproteins of therapeutic interest. N610 was also the primary site of sialylation of the receptor. See vol 283, pg 4460, 2008). A mineralization technique was developed that exposes carboxylate groups on the surface of cross-linked pHEMA, promoting high-affinity nucleation and growth of calcium phosphate on the surface, along with extensive calcification of the hydrogel interior. Here, we demonstrate that, relative to wild-type controls, ST8Sia IV(-/-) mice have a 30% reduction in total thymocytes and a concomitant deficiency in the earliest thymocyte precursors. View details for DOI 10.1096/fj.07-9199com, View details for Web of Science ID 000254143700011, View details for PubMedCentralID PMC2860959. A., Baskin, J. M., Bertozzi, C. R., Koberstein, J. T., Turro, N. J. View details for DOI 10.1096/fj.201601198R, View details for Web of Science ID 000401553400015, View details for PubMedCentralID PMC5434651, View details for DOI 10.1021/acscentsci.7b00204, View details for PubMedCentralID PMC5445543. A single multiwalled carbon nanotube attached to an atomic force microscope (AFM) tip was functionalized with cargo via a disulfide-based linker. Investigating Cell Surface Galectin-Mediated Cross-Linking on Glycoengineered Cells. Mycobacterium tuberculosis (Mtb), the causative agent of tuberculosis, is a highly evolved human pathogen characterized by its formidable cell wall. This strategy will prove useful for both the identification of O-GlcNAc-modified proteins and the elucidation of the specific residues that bear this saccharide. Given that M. tuberculosis typically persists in the phagosomal vacuole after being phagocytosed by macrophages, we performed a proteomic analysis of that organelle after treatment of macrophages with LAMs purified from the two mycobacterial species. View details for DOI 10.1073/pnas.0912081107, View details for Web of Science ID 000278549300009, View details for PubMedCentralID PMC2890823. Z., Uttamapinant, C., Poloukhtine, A., Baskin, J. M., Codelli, J. WebCarolyn Ruth Bertozzi (born October 10, 1966) is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. We recently introduced a method termed isotope-targeted glycoproteomics (IsoTaG), which utilizes isotope recoding to characterize azidosugar-labeled glycopeptides bearing fully intact glycans. To evaluate differential glycosylation in EOC caused by modulations in GALNT3 expression, we used a metabolic labeling strategy for enrichment and mass spectrometry-based characterization of glycoproteins following GALNT3 gene knockdown (KD) in A2780s EOC cells. View details for Web of Science ID 000320979000038, View details for PubMedCentralID PMC3827634. 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. View details for Web of Science ID 000296756600001, View details for PubMedCentralID PMC3219546. Belardi, B., de la Zerda, A., Spiciarich, D. R., Maund, S. L., Peehl, D. M., Bertozzi, C. R. A Chemical Glycoproteomics Platform Reveals O-GlcNAcylation of Mitochondrial Voltage-Dependent Anion Channel 2. This observation stood in stark contrast to the slow kinetics associated with 1,3-dipolar cycloaddition of azides with unstrained, linear alkynes, the conventional Huisgen process. This concise motif can be installed within heterologous proteins as a genetically encoded "aldehyde tag" for site-specific labeling with aminooxy- or hydrazide-functionalized probes. The glycosylation of serine and threonine residues with a single GlcNAc moiety is a dynamic posttranslational modification of many nuclear and cytoplasmic proteins. View details for DOI 10.1073/pnas.0809218105, View details for Web of Science ID 000260913800030, View details for PubMedCentralID PMC2579359. Sialylation, sulfation, and fucosylation appear to be required for the avid interaction of this ligand with L-selectin, but the exact carbohydrate structures involved in recognition remain undefined. The recently described O-glycoprotease OpeRATOR presents exciting opportunities for O-glycoproteomics. A., Agard, N. J., Lo, A., Bertozzi, C. R. Copper-Free Click Chemistry: Bioorthogonal Reagents for Tagging Azides, Cu-free click cycloaddition reactions in chemical biology, In Vivo Imaging of Caenorhabditis elegans Glycans, Symbol nomenclature for glycan representation. A genome-wide CRISPR screen identifies novel ligands for the Siglec family of glyco-immune checkpoint receptors. Vertebrate glycans constitute a large, important, and dynamic set of post-translational modifications that are notoriously difficult to manipulate and image. Zebrafish embryos were treated with an unnatural sugar to metabolically label their cell-surface glycans with azides. View details for DOI 10.1126/science.1155106, View details for Web of Science ID 000255454300046. As this special issue testifies, the field of bioorthogonal chemistry is firmly established as a challenging frontier of reaction methodology and an important new instrument for biological discovery. Muia, R. P., Yu, H., Prescher, J. Lipid-derived desiccation resistance in membranes is a rare, unique ability previously observed only with trehalose dimycolate (TDM), an abundant mycobacterial glycolipid. Proteomics analyses were also performed and confirmed enrichment of plasma membrane proteins with some contamination from endoplasmic reticulum and other membranes. In this report, we present a general strategy for dual-analyte detection in living animals that employs in situ formation of firefly luciferin from two complementary caged precursors that can be unmasked by different biochemical processes. Shao, Z., Flynn, R. A., Crowe, J. L., Zhu, Y., Liang, J., Jiang, W., Aryan, F., Aoude, P., Bertozzi, C. R., Estes, V. M., Lee, B. J., Bhagat, G., Zha, S., Calo, E. Deconvolution of Influenza a Viral Binding and Fusion with a Chemically-Defined Glycocalyx. This approach can highlight changes in physiology or environment and may be more informative than steady-state analyses. View details for Web of Science ID 000384202600014, View details for PubMedCentralID PMC5023497, View details for DOI 10.1021/acscentsci.5b00386, View details for PubMedCentralID PMC4827657. Bule, P. n., Chuzel, L. n., Blagova, E. n., Wu, L. n., Gray, M. A., Henrissat, B. n., Rapp, E. n., Bertozzi, C. R., Taron, C. H., Davies, G. J. In this study, we examined the possibility of selecting such antibodies from large phage antibody libraries using sulfotyrosine as a test case. The active site residues of Rv3406 and AtsK are essentially superimposable, suggesting that the two sulfatases share the same catalytic mechanism. Densely O-glycosylated mucin domains are found in a broad range of cell surface and secreted proteins, where they play key physiological roles. From 2006 to 2015 she was director of the Molecular Foundry, a nanoscience facility, at the Lawrence Berkeley National Laboratory. Hatzios, S. K., Baer, C. E., Rustad, T. R., Siegrist, M. S., Pang, J. M., Ortega, C., Alber, T., Grundner, C., Sherman, D. R., Bertozzi, C. R. Imaging the Glycosylation State of Cell Surface Glycoproteins by Two-Photon Fluorescence Lifetime Imaging Microscopy. Thus, to advance insight into the role of O-GlcNAc in T cell activation, we performed glycosite mapping studies via direct glycopeptide measurement on resting and activated primary human T cells with a technique termed Isotope Targeted Glycoproteomics. Mass spectrometry assays allowed us to identify other acceptors, mainly integrins. [85] Her father was of Italian descent. Pratt, M. R., Leigh, C. D., Bertozzi, C. R. A chemical approach for identifying O-GlcNAc-modified proteins in cells. Her research group profiles changes in cell surface glycosylation associated with cancer, inflammation and bacterial infection, and uses this information to develop new Sialome sweet sialome: As sialic acids are involved in many host-pathogen recognition events and are markers of embryonic and malignant tissues, there is great interest in methods for the enrichment and identification of sialylated glycoproteins from complex tissues. Inhibitors of a key step of O-linked glycan biosynthesis can be discovered from a directed library screen. 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. Collectively, these results indicate that the distortion/interaction model combined with bond angle analysis will enable predictions of cyclooctyne reactivity and the rational design of new reagents for copper-free click chemistry. Despite its broad functional significance, the dynamic and posttranslational nature of O-GlcNAc signaling makes it challenging to study using traditional molecular and cell biological techniques alone. These tools have identified potential disease biomarkers and ways to monitor dynamic changes to the glycome in living organisms. Furthermore, we developed a biomemetic coating strategy to interface BNNTs with proteins and cells. The effort was enabled by a new high-fidelity pattern-searching and glycopeptide validation algorithm termed IsoStamp v2.0, as well as by novel stable isotope probes. These cells were used as substrates to examine the effect of inhibiting PSA synthesis on the development of neurons derived from the chick dorsal root ganglion. Prof. Bertozzi has been recognized with many honors and awards for both her research and teaching accomplishments. The cell-surface repertoire can be expanded to include abiotic functionality through the biosynthetic introduction of unnatural sugars into cellular glycans, a process termed metabolic oligosaccharide engineering. Barnes, J., Kaushik, S., Bainer, R. O., Sa, J. K., Woods, E. C., Kai, F., Przybyla, L., Lee, M., Lee, H., Tung, J. C., Maller, O., Barrett, A. S., Lu, K. V., Lakins, J. N., Hansen, K. C., Obernier, K., Alvarez-Buylla, A., Bergers, G., Phillips, J. J., Nam, D., Bertozzi, C. R., Weaver, V. M. Glycosyltransferase bump-hole engineering to dissect mucin-type O-glycosylation in the living cell. Specific labeling of biomolecules with biochemical and biophysical probes is a central element of proteomics research. Molecules terminated with Texas Red lie flat at the membrane (height, 0 +/- 2 nm), implying that interactions between Texas Red and the bilayer dominate the polymers' free energy. View details for DOI 10.1073/pnas.252514899, View details for Web of Science ID 000180101600095, View details for PubMedCentralID PMC139265. Synthetic mimics of the complex assemblies found on cell surfaces can modulate cellular interactions and are under development as therapeutic agents. She is a member of the National Academy of Sciences (2005), the Institute of Medicine (2011), and the National Academy of Inventors (2013). However, only some of these mutants were able to generate protection equivalent to that of BCG in mice. Cyclodextrin complexation is therefore a promising approach for stabilizing compounds that possess the high intrinsic reactivities desired for Cu-free click chemistry. Although hundreds of proteins are known to be modified by O-GlcNAc, a strict amino acid consensus sequence for OGT has not been identified. In contrast, exogenous (13)C-labeled N-acetylneuraminic acid ([(13)C]NeuAc) and N-glycolylneuraminic acid (NeuGc) were efficiently incorporated into LOS in a dose-dependent fashion. 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. They write new content and verify and edit content received from contributors. Cotranslational modification of the proteins by FGE produced products bearing a unique aldehyde group. [6] Her lab's development of nanotechnologies which probe biological systems lead to the development of a fast point-of-care tuberculosis test in 2018. View details for Web of Science ID 000085902800059. This challenging process made her dream of Although genetically encoded tags such as GFP are widely used to monitor discrete proteins, they can cause significant perturbations to a protein's structure and have no direct extension to other classes of biomolecules such as glycans, lipids, nucleic acids and secondary metabolites. We used this method to identify interaction partners for the O-GlcNAc-modified FG-repeat nucleoporins. Molecular imaging enables visualization of specific molecules in vivo and without substantial perturbation to the target molecule's environment. View details for Web of Science ID 000305107800004, View details for PubMedCentralID PMC3374418. Welch Award in Chemistry (2022); The Dickson Prize in Medicine, University of Pittsburgh (2022); Dr H.P. Finally, mechanistic and structural data from sulfate-assimilation enzymes have revealed how M. tb controls the flux of sulfate in the cell. Biological analysis of diptericin fragments indicated that the main determinant of antibacterial activity lay in the C-terminal region that is similar to the attacin peptides, although the N-terminal segment, related to the proline-rich family of antibacterial peptides, augmented that activity by 100-fold. ppGalNAc T1 and T2 revealed no significant enhancements suggesting Ser/Thr-O-GalNAc was inhibitory at most positions for these isoforms. 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. She has been recognized with many honors and awards for her research accomplishments. Our observations are the first reported instance of dehydration resistance provided by a membrane glycolipid. Mycobacterium tuberculosis synthesizes specific polyketide lipids that interact with the host and are required for virulence. Nevertheless, CD45 remained to be the main acceptor. Baker Family Director of Stanford ChEM-H, Anne T. and Robert M. Bass Professor in the School of Humanities and Sciences and Professor, by courtesy, of Chemical and Systems Biology and of Radiology, AB, Harvard University, Chemistry (1988). Calculated values of dissociation constants for the complexes indicate that AMP binds with a higher affinity to the enzyme intermediate than to the free enzyme. Unlike existing systems for controlling gene expression in Mtb, the riboswitch does not require the co-expression of any accessory proteins: all of the regulatory machinery is encoded by a short DNA segment directly upstream of the target gene. Here, we report technology for covalent, specific tagging of cellular proteins with chemical probes. We structurally assigned 32 N-glycopeptides and over 500 intact and fully elaborated O-glycopeptides from 250 proteins across three human cancer cell lines and also discovered unexpected peptide sequence polymorphisms (pSPs). View details for Web of Science ID 000250260500015. The polypeptide N-acetyl-alpha-galactosaminyltransferases (ppGalNAcTs, also abbreviated ppGaNTases) initiate mucin-type O-linked glycosylation and therefore play pivotal roles in cell-cell communication and protection of tissues. Proteins bearing this "aldehyde tag" were chemically modified by selective reaction with hydrazide- or aminooxy-functionalized reagents. Lin, F. L., Hoyt, H. M., van Halbeek, H., Bergman, R. G., Bertozzi, C. R. Synthetic glycopeptides and glycoproteins as tools for biology, Functional hydrogel-biomineral composites inspired by natural bone, Azido sialic acids can modulate cell-surface interactions, A small-molecule switch for Golgi sulfotransferases. Co-opting cellular factors for viral translation and viral genome replication at the endoplasmic reticulum is a shared replication strategy, despite different clinical outcomes. In July 2020, Carolyn Bertozzi, Ph.D. and her team at Stanford University published a transformational paper that characterized a new class of molecules called lysosome-targeting chimeras, or LYTACs. Myristoylation is the attachment of the 14-carbon fatty acid myristate to the N-terminal glycine residue of proteins. Among the EMBs loci were genes encoding RipC and the FtsEX complex, a PG cleaving enzyme required for proper cell division and its predicted regulator, respectively. Oligosaccharides on proteins and lipids play central roles in human health and disease. Applications to the visualization of cellular glycans and enrichment of glycoproteins for proteomic analysis are described. Potential for therapeutics and diagnostics, Kinetic measurements and mechanism determination of Stf0 sulfotransferase using mass spectrometry. Exogenously supplied N-acetylmannosamine analogues were not converted to LOS-associated sialosides at a detectable level. A sensitive electrospray ionization mass spectrometry-based assay was used to extract the kinetic parameters for PAP, revealing a K m (8.1 +/- 3.1 microM) and k cat (5.4 +/- 1.1 s (-1)) comparable to those reported for other CysQ enzymes. View details for Web of Science ID 000088039800042. Agarwal, P., Beahm, B. J., Shieh, P., Bertozzi, C. R. Live-Cell Labeling of Specific Protein Glycoforms by Proximity-Enhanced Bioorthogonal Ligation. Employing the Huisgen 1,3-dipolar cycloaddition of azides and alkynes, we examined crosslinking of cognate NRPS modules within the tyrocidine pathway and demonstrated the sensitivity of our panel of crosslinking probes toward the selective protein interactions of compatible COM domains. This tutorial review will summarize the history of this emerging field, as well as recent progress in the development and application of bioorthogonal copper-free click cycloaddition reactions. We previously described a chemical method to image glycans during zebrafish larval development; however, we were unable to detect glycans during the first 24 hours of embryogenesis, a very dynamic period in development. 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. Glycans are central to many biological processes, but efforts to define their functions at the molecular level have been frustrated by a lack of suitable technologies. Our results demonstrate a key role of PIKfyve in the processing and presentation of antigens, which should be taken into consideration when targeting PIKfyve in autoimmune disease and cancer. The approach was validated by labeling a recombinant glycoprotein that is known to possess O-linked glycans with GalNAz. Bertozzi is a member of the Royal Society and the academies of sciences of Germany and the United States. 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). On the basis of these results, we propose possible pathways for 6-sulfo sialyl Lewis x biosynthesis and suggest that sulfation may be an early committed step. A., Krishnan, V., Pett, C., Yu, J., Woods, E. C., Kramer, J. R., Westerlind, U., Dorigo, O., Bertozzi, C. R. CD22 blockade restores homeostatic microglial phagocytosis in ageing brains. Kinetic studies revealed significant inhibitory activity and provide guidance for improved inhibitor design. These two strategies provide a means to selectively modify cell-surface glycans with exogenous probes. In this report, we seek to expand the functional repertoire of such transformations by introducing a new bond-cleaving reaction between N-oxide and boron reagents. She is currently a professor of Chemistry, Chemical and Systems Biology, and Radiology at Stanford University, and an Investigator at the Howard Hughes Medical Institute. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed for direct covalent modification of biomolecules with probes in the mouse, an important model organism for studies of human disease. View details for DOI 10.1074/jbc.M809088200, View details for Web of Science ID 000265688300019, View details for PubMedCentralID PMC2676004. Bhakta, S., Bartes, A., Bowman, K. G., Kao, W. M., Polsky, I., Lee, J. K., Cook, B. N., Bruehl, R. E., ROSEN, S. D., Bertozzi, C. R., Hemmerich, S. New directions in glycoprotein engineering, Minimal sulfated carbohydrates for recognition by L-selectin and the MECA-79 antibody. Here we present the first step toward bottom-up assembly of model cell surfaces-the synthesis of mucin mimetics and their incorporation into artificial membranes. The detailed quantitative parameters of ManLev metabolism in human and nonhuman-derived cell lines were determined to establish a foundation for the modification of cell surfaces with novel epitopes at defined cell-surface densities. Bertozzi is the only female scientist to have been awarded a science Nobel prize this year, after an all-male line-up in 2021. The antibody-sialidase conjugate desialylated tumor cells in a HER2-dependent manner, reduced binding by natural killer (NK) cell inhibitory sialic acid-binding Ig-like lectin (Siglec) receptors, and enhanced binding to the NK-activating receptor natural killer group 2D (NKG2D). The structure of CysN*D shows the two proteins in tight association; however, the nucleotides bound to each subunit are spatially segregated. The unique chemical functionality of these analogs is exploited for selective attachment of singlet oxygen-generating fluorescent dyes via bioorthogonal 'click chemistry' ligations. Individuals with GeneXpert-positive pulmonary TB were sampled pre-treatment over 60-minutes. (2001) Glycobiology 11, 11R-18R]. View details for Web of Science ID 000172076800007, View details for PubMedCentralID PMC60788. These results should facilitate mechanistic studies and the development of small molecule inhibitors of this enzyme family to ameliorate chronic inflammatory diseases. The ability to access glycopeptides of this type through chemical synthesis will facilitate further mechanistic studies. Penetration of cell membranes with this "nanoneedle" was controlled by the AFM. 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. The reaction features a large dynamic range of reactivity, showcasing second-order rate constants as high as 2.310(3) M(-1) s(-1) using diboron reaction partners. A broader theme that emerged was the urgent need to bring the glycosciences back into the mainstream of biology by integrating relevant education into the curricula of medical, graduate, and postgraduate training programs, thus generating a critical sustainable workforce that can advance the much-needed translation of glycosciences into a more complete understanding of biology and the enhanced practice of medicine. She coined the term "bioorthogonal chemistry" for chemical reactions compatible with living systems. View details for Web of Science ID 000075388100009. Liposomes displaying 3'-sulfo Lewis(X)-like oligosaccharides, on the other hand, show slight loss of binding with introduction of additional anionic functional groups for E- and P-selectin and negligible change for L-selectin. The unique labeling strategy of BCG by CDG-Tre provides a versatile tool for tracking Mtb in both pre- and post-phagocytosis and elucidating fundamental physiological and pathological processes related to the mycomembrane. Our editors will review what youve submitted and determine whether to revise the article. However, the synthetic difficulties inherent to sialylated and fucosylated oligosaccharides motivate the search for alternative antagonists. Sletten, E. M., Nakamura, H., Jewett, J. C., Bertozzi, C. R. Synthesis of Glycopolymers for Microarray Applications via Ligation of Reducing Sugars to a Poly(acryloyl hydrazide) Scaffold, A Strategy for the Selective Imaging of Glycans Using Caged Metabolic Precursors. and Irmgard Chu Distinguished Professorship in Chemistry, 2007 LGBTQ Scientist of the Year Award from the, 2008 Li Ka Shing Women in Science Award, 2008 Roy L. Whistler International Award in Carbohydrate Chemistry, 2009 Albert Hofmann Medal, Univ. Our editors will review what youve submitted and determine whether to revise the article spectrometry! To characterize azidosugar-labeled glycopeptides bearing fully intact glycans elucidation of the proteins by FGE produced bearing. These two strategies provide a means to selectively modify cell-surface glycans with azides ID 000180101600095, View details Web! Equivalent to that of BCG in mice DOI 10.1073/pnas.0809218105, View details for DOI 10.1073/pnas.0912081107, details! 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