The acquisition of the sialyl residue allows the parasite to avoid lysis by serum factors and to interact with the host cell. Hang, H. C., Yu, C., Kato, D. L., Bertozzi, C. R. Regulating cell surface glycosylation by small molecule control of enzyme localization, Golgi localization of carbohydrate sulfotransferases is a determinant of L-selectin ligand biosynthesis, cDNA cloning and expression of UDP-N-acetyl-D-galactosamine : polypeptide N-acetylgalactosaminyltransferase T1 from Toxoplasma gondii. 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. Breidenbach, M. A., Palaniappan, K. K., Pitcher, A. T-cell progenitors originate in the bone marrow and are mobilized to the blood at regular intervals by unknown signals. Kehoe, J. W., Maly, D. J., Verdugo, D. E., Armstrong, J. I., Cook, B. N., Ouyang, Y. Ahn, G., Banik, S. M., Miller, C. L., Riley, N. M., Cochran, J. R., Bertozzi, C. R. Degradation from the outside in: targeting extracellular and membrane proteins for degradation through the endolysosomal pathway. Their localization was correlated with preferred activity on either N-linked or O-linked glycoproteins. These reactions possess extreme selectivity and biocompatibility, such that their participating reagents can form covalent bonds within richly functionalized biological systems--in some cases, living organisms. Cell surface reactions of this kind should prove useful in the introduction of new recognition epitopes, such as peptides, oligosaccharides, or small organic molecules, onto cell surfaces and in the subsequent modulation of cell-cell or cell-small molecule binding events. View details for Web of Science ID 000187945400003. Bhat, R., Belardi, B., Mori, H., Kuo, P., Tam, A., Hines, W. C., Quynh-Thu Le, Q. T., Bertozzi, C. R., Bissell, M. J. View details for DOI 10.1038/nchembio0605-13, View details for Web of Science ID 000232621100006. New developments have allowed researchers to begin probing the inner workings of the cell to gain new insight into cell function and metabolism. This review presents an overview of techniques for examining and manipulating cell surface oligosaccharides through genetic, enzymatic, and chemical strategies. Mauris, J., Mantelli, F., Woodward, A. M., Cao, Z., Bertozzi, C. R., Panjwani, N., Godula, K., Argueeso, P. Sulfatase-activated fluorophores for rapid discrimination of mycobacterial species and strains. 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. Here, we tracked the assembly dynamics of different envelope layers in Corynebacterium glutamicum and Mycobacterium smegmatis by using metabolic labeling and found that the septal cell envelope is assembled sequentially in both species. Glycosylation is a prevalent, yet heterogeneous modification with a broad range of implications in molecular biology. 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. Bertozzi subsequently optimized the bioorthogonal reaction using an azide as a binding partner for the fluorescent tag. We use this framework to assess existing data and to ask the question, "How many distinct primary structures of proteins (proteoforms) are created from the 20,300 human genes?" A. Sequential assembly of the septal cell envelope prior to V snapping in Corynebacterium glutamicum. Glycans can be imaged by metabolic labeling with azidosugars followed by chemical reaction with imaging probes; however, tissue-specific labeling is difficult to achieve. Metabolic incorporation of d-alanine derivatives and click chemistry detection constitute a facile, modular platform that facilitates unprecedented spatial and temporal resolution of PG dynamics in vivo. View details for Web of Science ID 000285812000039, View details for PubMedCentralID PMC3018347. We anticipate that this chemical method will find broad use in epigenetics to enable unbiased searches for new PKMT substrates by using recombinant enzymes and unnatural SAM cofactors to label and purify many substrates simultaneously from complex organelle or cell extracts. Ac4GalNAz treatment labeled the surface of healthy mouse corneas, leaving most cells viable, and bacteria preferentially associated with GalNAz-labeled regions. Here, we demonstrate that cysQ disruption attenuates Mtb growth in vitro and decreases the biosynthesis of sulfated glycolipids but not major thiols, suggesting that the encoded enzyme specifically regulates mycobacterial sulfation. Finally, the structure of an intermediate that accumulates under anhydrous conditions was identified. Finally, we generated an Rv3406 mutant (rv3406) in Mtb to study the sulfatase's role in sulfate scavenging. Experimental data confirmed that electronic perturbation of BARAC's aryl rings has a modest effect on reaction rate, whereas steric hindrance in the transition state can significantly retard the reaction. Mahal, L. K., Yarema, K. J., Bertozzi, C. R. An ELISA for selectins based on binding to a physiological ligand. 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 combined CRISPR-Cas9 knockout screens with RNAsequencing analysis to discover age-related genetic modifiers of microglial phagocytosis. Thus, choice of enrichment strategy has profoundimplications on experimental outcomes. View details for DOI 10.1016/j.molcel.2005.10.034, View details for Web of Science ID 000234764700011. Incorporation of sialosides into LOS was assessed by matrix-assisted laser desorption and electrospray ionization mass spectrometry. Branching morphogenesis in the mammary gland is achieved by the migration of epithelial cells through a microenvironment consisting of stromal cells and extracellular matrix (ECM). This assembly inhibits L-, E-, and P-selectin binding to GlyCAM-1, a physiological ligand better than sLe(x)-like liposomes without additional anionic charge. The approach was applied to the sialic acid metabolic pathway in human cells, yielding novel mutants with phenotypes related to the inborn metabolic defect sialuria and metastatic tumor cells. Hemmerich, S., Bertozzi, C. R., Leffler, H., ROSEN, S. D. FLUORESCENCE PROBES IN BIOCHEMISTRY - AN EXAMINATION OF THE NONFLUORESCENT BEHAVIOR OF DANSYLAMIDE BY PHOTOACOUSTIC CALORIMETRY. Here we investigate the behavior of these GPI-protein analogs in living cells. Time-resolved measurements yield the binding rate between the particles and bacteria. CDG-Tre showed high selectivity for mycobacteria over other clinically prevalent species in the Corynebacterineae suborder. Targets intended for clearance expose ligands that initiate their phagocytosis ("eat me" signals), while others avoid phagocytosis by displaying inhibitory ligands ("don't eat me" signals). These studies establish Cu-free click chemistry as a bioorthogonal reaction that can be executed in the physiologically relevant context of a mouse. Metabolic conversion of ManNAz to N-azidoacetylsialic acid (SiaNAz) within membrane-bound and secreted glycoproteins was quantified in a variety of cell types. Antibodies bind to and agglutinate synthetic antigen-DNA conjugates, enabling ligation of the DNA strands and subsequent quantification by qPCR. 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). We used this method to identify interaction partners for the O-GlcNAc-modified FG-repeat nucleoporins. Here, a sequence-based analysis of newly discovered mycobacterial sulfotransferase genes, named stf1-stf10, is presented. Deletion of CysH from M. smegmatis afforded a cysteine and methionine auxotroph consistent with a metabolic branch point centered on APS. Laughlin, S. T., Agard, N. J., Baskin, J. M., Carrico, I. S., Chang, P. V., Ganguli, A. S., Hangauer, M. J., Lo, A., Prescher, J. A., Rajaiah, G., Falck, J. R., Bertozzi, C. R., Berthiaume, L. G. Identification of palmitoylated mitochondrial proteins using a bio-orthogonal azido-palmitate analogue. A computational model predicted that these glycoproteins would influence transmembrane receptor spatial organization and function. Professor Carolyn Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface sugars important to human health and disease. This review highlights the development of bioorthogonal chemical reporters and reactions and their application in living systems. The application of a chemical biology approach for the metabolic labeling and subsequent characterization of O-glycoproteins in EOC using the Ac4GalNAz metabolite has provided a strategy allowing for proteomic discovery of GalNAc-Ts specific functions. Manning, D. D., Bertozzi, C. R., ROSEN, S. D., Kiessling, L. L. C-glycosyl aldehydes: Synthons for C-linked disaccharides. Here we explore an alternative bioorthogonal reaction, the 1,3-dipolar cycloaddition of azides and cyclooctynes, also known as "Cu-free click chemistry," for labeling biomolecules in live mice. Here, we describe the broad application of the method to analyze glycoproteomes from a collection of tissue-diverse cell lines. Li phin vn-chng si to pan-lan-chhan , ng cho-tet yung phin-si fet-ch khok-chhng kh ke nui-yng. Tsui, C. K., Barfield, R. M., Fischer, C. R., Morgens, D. W., Li, A., Smith, B. Pi, N., Hoang, M. B., Gao, H., Mougous, J. D., Bertozzi, C. R., Leary, J. The glycosylphosphatidylinositol (GPI) anchor is a C-terminal posttranslational modification found on many eukaryotic proteins that reside in the outer leaflet of the cell membrane. We previously synthesized a series of GPI anchor analogs with systematic deletions within the glycan core and coupled them to the GFP by a combination of expressed protein ligation and native chemical ligation [Paulick MG, Wise AR, Forstner MB, Groves JT, Bertozzi CR (2007) J Am Chem Soc 129:11543-11550]. 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. Previously, we described the biochemical activity of the sulfotransferase Stf0 that initiates SL-1 biosynthesis. Tumors which remodel their glycocalyces, by overexpressing bulky glycoproteins like mucins, exhibit a higher predisposition to metastasize, but the role of mucins in oncogenesis remains poorly understood. These enzymes often comprise large families. The average overall agreement between ADAP and radioassay was above 91%. Measurements from the ADAP assay were compared to radioassay to determine correlation, concordance, agreement, clinical sensitivity and specificity. A comparative study of bioorthogonal reactions with azides. Delaveris, C. S., Chiu, S. H., Riley, N. M., Bertozzi, C. R. The clinical impact of glycobiology: targeting selectins, Siglecs and mammalian glycans. A cell metabolic labeling experiment can be completed in approximately 4 d. View details for DOI 10.1038/nprot.2007.422, View details for Web of Science ID 000253140000033. View details for DOI 10.1016/j.chembiol.2004.05.009, View details for Web of Science ID 000222987300018, View details for DOI 10.1002/cbic.200300789, View details for Web of Science ID 000220196800018. View details for Web of Science ID 000237590400012. View details for DOI 10.1073/pnas.0809218105, View details for Web of Science ID 000260913800030, View details for PubMedCentralID PMC2579359. View details for Web of Science ID 000310103800025, View details for PubMedCentralID PMC3596100. Laureates [3] [ edit] Laureates per country [ edit] Both the activity and specificity of the inducible enzymes were indistinguishable from their WT counterparts. We report herein the chemical synthesis and preliminary mechanistic investigation of diptericin, an 82 residue glycopeptide that contains regions similar to two different types of antibacterial peptides. The following reductive cleavage of the disulfide bonds within the cell's interior resulted in the release of cargo inside the cells, after which the nanoneedle was retracted by AFM control. A chimera comprising the localization domain of GlcNAc6ST-1 fused to the catalytic domain of GlcNAc6ST-2 was confined to the trans-Golgi network and adopted the substrate preference of GlcNAc6ST-1. Indeed, O-glycopeptides modified exclusively at the N-terminus would enable O-glycoproteomic methods to rely solely on collision-based fragmentation rather than electron-driven dissociation because glycan-retaining peptide fragments would not be required for localization. A key feature of SiaLev is the presence of a ketone group that can be exploited in chemoselective ligation reactions to deliver small-molecule probes to the cell surface. Myoblast cells were patterned with high efficiency and remained undifferentiated after surface attachment. View details for Web of Science ID 000224032900044. Herein, we have used biochemical, spectroscopic, and mass spectrometry analysis to investigate the iron-sulfur cluster and its role in the mechanism of Mycobacterium tuberculosis APS reductase. Humans do not possess a homologous metabolic pathway, and thus, these enzymes represent attractive targets for therapeutic intervention. Metabolic labeling with GalNAz followed by Staudinger ligation provides a means for proteomic analysis of this posttranslational modification and for identifying O-linked glycoprotein fingerprints associated with disease. Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. 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. These results should facilitate mechanistic studies and the development of small molecule inhibitors of this enzyme family to ameliorate chronic inflammatory diseases. View details for DOI 10.1074/jbc.M109.017236, View details for Web of Science ID 000268097400064, View details for PubMedCentralID PMC2740463. These products represent a new class of engineered biosimilars bearing novel glycodendrimer structures. From 2006 to 2015 she was director of the Molecular Foundry, a nanoscience facility, at the Lawrence Berkeley National Laboratory. Carolyn Bertozzi, PhD, was one of three scientists to be awarded the 2022 Nobel Prize in Chemistry earlier today for the development of click chemistry and bio-orthogonal chemistry. The IsoTaG platform is broadly applicable to the discovery of PTM sites that are amenable to chemical labeling, as well as previously unknown protein isoforms including pSPs. 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. Incorporation of azide-functionalized amino acids into proteins in vivo provides opportunities for protein modification under native conditions and selective labeling of proteins in the intracellular environment. Analyses revealed that recurrent GBMs have increased tension and express high levels of glycoproteins that increase the bulkiness of the glycocalyx. A major drawback to studying the sialylation kinetics and turnover of the trypomastigote glycoconjugates is the difficulty to identify and follow the recently acquired sialyl residues. The GlcNAc-6-0 sulfotransferase that installs the sulfate ester may be a key modulator of lymphocyte recruitment to secondary lymphoid organs and sites of chronic inflammation and is therefore a potential target for anti-inflammatory therapy.A GlcNAc-6-0-sulfotransferase activity was identified within porcine lymph nodes and characterized using a rapid, sensitive, and quantitative assay. Robust surface mineral layers a few microns thick were obtained. A revised, highly practical synthesis of the precursor N(alpha)-Fmoc-Thr(Ac(3)-alpha-D-GalNAc) allowed us to produce sufficient quantities of the glycopeptide for mechanistic assays. The resulting trehalose biosynthesis mutant was unable to proliferate and enter stationary phase unless supplemented with trehalose. The mobility of CD45 increased markedly upon engagement of Fc receptors. Rv3406 was identified based on its homology to the alkyl sulfatase AtsK from Pseudomonas putida. These uridine analogs represent the first generation of chemical tools to study the functions of mucin-type O-linked glycosylation. End-functionalization with a hydrophobic anchor permitted incorporation into the membranes of live cultured cells. With this technique, we studied the dynamics of glycan trafficking and identified a population of sialoglycoconjugates with unexpectedly rapid internalization kinetics. To accomplish this goal, we took advantage of the bioorthogonal chemical reporter technique. The azide, being nonreactive within cells, was ideal for use in living systems. We further show that proteins containing azidohomoalanine can be selectively modified in the presence of other cellular proteins by means of Staudinger ligation with triarylphosphine reagents. The phosphine-luciferin probe is therefore poised for many applications in real-time imaging in cells and whole animals. 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