Thus, the protein-carbohydrate interactions, as well as other interactions contributing to ligand recognition, can be investigated. 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. View details for Web of Science ID 000207584000003, View details for PubMedCentralID PMC138933. View details for Web of Science ID 000180258800025, View details for Web of Science ID 000181755600011, View details for Web of Science ID 000185102400018. The polyvalent display of carbohydrate groups found on cell surface glycoprotein structures may contribute to the enhanced binding strength of selectin-mediated adhesion. View details for DOI 10.1073/pnas.2335201100, View details for Web of Science ID 000187227200045, View details for PubMedCentralID PMC299823. Discovery and functional interrogation of SARS-CoV-2 RNA-host protein interactions. Metabolic labeling of glycans with synthetic sugar analogs has emerged as an attractive means for introducing nonnatural chemical functionality into glycoproteins. We demonstrate here that a previously uncharacterized sulfated molecule, termed S881, is localized to the outer envelope of M. tuberculosis and negatively regulates the virulence of the organism in two mouse infection models. While individual CD45 molecules moved randomly, they were displaced from the advancing phagocytic cup by an expanding diffusional barrier. 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. To increase the utility of bioaerosol sampling, we present advances in bioaerosol collection and Mtb identification that improve detection yields.A previously described Respiratory Aerosol Sampling Chamber (RASC) protocol, or "RASC-1", was modified to incorporate liquid collection of bioaerosol using a high-flow wet-walled cyclone (RASC-2). She has found a smart way to connect cells together. Saxon, E., Luchansky, S. J., Hang, H. C., Yu, C., Lee, S. C., Bertozzi, C. R. Carbohydrate sulfotransferases of the GalNAc/Gal/GlcNAc6ST family, Kinetic analysis of NodST sulfotransferase using an electrospray ionization mass spectrometry assay. Phosphorylation of Rv0516c regulated the abundance of EspA, a virulence-associated substrate of the type VII ESX-1 secretion system. We discuss the use of fluorescent and fluorogenic trehalose probes for the detection of the mycobacterial trehalose glycolipids. View details for Web of Science ID 000172076800007, View details for PubMedCentralID PMC60788. The approach was validated by labeling a recombinant glycoprotein that is known to possess O-linked glycans with GalNAz. Converse, S. E., Mougous, J. D., Leavell, M. D., Leary, J. View details for Web of Science ID 000255629400034, View details for PubMedCentralID PMC2724873. The recently described O-glycoprotease OpeRATOR presents exciting opportunities for O-glycoproteomics. The latter include a glycosyltransferase 1 (GT1) motif containing a DXH sequence, a Gal/GalNAc-T motif, and a region homologous to ricin lectin. An, H. J., Gip, P., Kim, J., Wu, S., Park, K. W., McVaugh, C. T., Schaffer, D. V., Bertozzi, C. R., Lebrilla, C. B. Metabolic labeling enables selective photocrosslinking of O-GlcNAc-modified proteins to their binding partners. Carol Bertozzi, a Stanford University chemist, won the Nobel Prize in chemistry in 2022. Live cell imaging is a powerful method to study protein dynamics at the cell surface, but conventional imaging probes are bulky, or interfere with protein function, or dissociate from proteins after internalization. View details for Web of Science ID 000177297600001. To elevate the reactivities of cyclooctynes, two strategies, LUMO lowering through propargylic fluorination and strain enhancement through fused aryl rings, have been explored. This method is rapid and efficient, allowing virtually any mammalian cell to be patterned on surfaces bearing complementary DNA in under 1 h. We demonstrate this technique using several types of cells that are generally incompatible with integrin-targeting approaches, including red blood cells and primary T-cells. Nessen, M. A., Kramer, G., Back, J., Baskin, J. M., Smeenk, L. E., de Koning, L. J., van Maarseveen, J. H., de Jong, L., Bertozzi, C. R., Hiemstra, H., de Koster, C. G. Direct Cell Surface Modification with DNA for the Capture of Primary Cells and the Investigation of Myotube Formation on Defined Patterns. For example, chemical glycoproteomics technologies have enabled the identification of specific glycosylation sites and glycan structures that modulate protein function in a number of biological processes. PKMTs are likely to have many additional substrates in addition to histones, but relatively few nonhistone substrates have been characterized, and the substrate specificity for many PKMTs has yet to be defined. Paulk, N. K., Rumachik, N., Malaker, S., Adams, C., Leib, R., Bertozzi, C. R., Kay, M. Award Address (Arthur C. Cope Award sponsored by the Arthur C. Cope Fund). Abnormalities in the synthesis or presentation of these carbohydrates can lead to misfolded and inactive proteins, as well as to several debilitating disease states. A FRET-based fluorogenic phosphine for live-cell Imaging with the Staudinger ligation, DNA-Coated AFM Cantilevers for the Investigation of Cell Adhesion and the Patterning of Live Cells. This pathway is regulated by diverse environmental cues and regulatory proteins that mediate sulfur transactions in the cell. Numerous factors that influence cell-surface carbohydrate composition remain to be elucidated. 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. CDG-Tre fluoresces upon activation by BlaC, the -lactamase uniquely expressed by Mtb, and the fluorescent product is subsequently incorporated within the bacterial cell wall via trehalose metabolic pathway. View details for DOI 10.1016/j.cell.2015.11.048, View details for PubMedCentralID PMC4715264. Assimilatory 3'-phosphoadenosine 5'-phosphosulfate (PAPS) reductases are evolutionarily related, homologous enzymes that catalyze the same overall reaction, but do so in the absence of an [Fe-S] cluster. Carroll, K. S., Gao, H., Chen, H. Y., Stout, C. D., Leary, J. A., Bertozzi, C. R., Stout, C. D. A chemical reporter strategy to probe glycoprotein fucosylation. The ability to access glycopeptides of this type through chemical synthesis will facilitate further mechanistic studies. These findings suggest a dual role for trehalose as both a thermoprotectant and a precursor of critical cell wall metabolites. 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. Her efforts in undergraduate education have earned her the UC Berkeley Distinguished Teaching Award and the Donald Sterling Noyce Prize for Excellence in Undergraduate Teaching. To this end, we generated the first high-density library of transposon insertion mutants in the model organism C. glutamicum. To our knowledge, this is the first example of a sulfated menaquinone produced in any prokaryote. We also explore prospects for improving measurements to better regularize protein-level biology and efficiently associate PTMs to function and phenotype. These observations suggest crosstalk between autophagy and phagocytosis that may be relevant to the innate immune response of macrophages. In this study, we describe the development of a high-throughput assay for OGT and use it to profile the specificity of the enzyme among a panel of peptide substrates. More generally, the generation of recombinant glycoproteins containing chemical handles within their glycans provides a means for studying their behavior and for improving their in vivo efficacy. Our method imparts N-glycopeptide mass envelopes with a pattern that is computationally distinguishable from background ions. She also held an appointment as a professor of molecular and cellular pharmacology from 2000 to 2002 at the University of California, San Francisco. Wei, W., Riley, N. M., Yang, A. C., Kim, J. T., Terrell, S. M., Li, V. L., Garcia-Contreras, M., Bertozzi, C. R., Long, J. View details for DOI 10.1073/pnas.1012864107, View details for Web of Science ID 000285521500020, View details for PubMedCentralID PMC3003011. Finally, mechanistic and structural data from sulfate-assimilation enzymes have revealed how M. tb controls the flux of sulfate in the cell. 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. [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". Affiliation at the time of the award: Stanford University, Stanford, CA, USA; Grand Challenges in Chemistry for 2016 and Beyond. Little is known about how cells respond on a molecular level to tissue engineering scaffold materials. In this study we have examined how unnatural sialic acids can alter polysialic acid expression and influence the adhesive properties of the neural cell adhesion molecule (NCAM). In addition, we solved the crystal structure of the Streptomyces coelicolor FGE homolog to 2.1 A resolution. Woo, C. M., Felix, A., Byrd, W. E., Zuegel, D. K., Ishihara, M., Azadi, P., Iavarone, A. T., Pitteri, S. J., Bertozzi, C. R. Click-Chemistry Based High Throughput Screening Platform for Modulators of Ras Palmitoylation. This hypothesis reflects the known oligomeric states of the galectins themselves and their binding properties with multivalent ligands in vitro, but direct evidence of their ability to cross-link ligands on a cell surface is lacking. Progenitors lacking polySi exhibited a specific defect in T-cell development because of an inability to access the thymus. Here we demonstrate that information gained from the biochemical analysis of a physiological selectin ligand can provide new leads for small molecule design. Zhou, X., Rodriguez-Rivera, F. P., Lim, H. C., Bell, J. C., Bernhardt, T. G., Bertozzi, C. R., Theriot, J. Photoacoustic calorimetry combined with established absorption and fluorescence methodologies provides a complete arsenal for characterizing the photophysical properties of many systems. One such glycolipid, Sulfolipid-1 (SL-1), consists of a trehalose-2-sulfate (T2S) core acylated with four lipid moieties. The high signal-to-background ratio obtained using nanomolar concentrations of BARAC obviated the need for washing steps. The machinery responsible for sulfatase activation is poorly understood in prokaryotes. 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. Characterization of the metabolic fates of four TreAz analogues revealed unique labeling routes that can be harnessed for pathway-targeted investigation of the mycobacterial trehalome. Genomic and proteomic profiling form a basis for biological discovery. Agre, P., Bertozzi, C., Bissell, M., Campbell, K. P., Cummings, R. D., Desai, U. R., Estes, M., Flotte, T., Fogleman, G., Gage, F., Ginsburg, D., Gordon, J. I., Hart, G., Hascall, V., Kiessling, L., Kornfeld, S., Lowe, J., Magnani, J., Mahal, L. K., Medzhitov, R., Roberts, R. J., Sackstein, R., Sarkar, R., Schnaar, R., Schwartz, N., Varki, A., Walt, D., Weissman, I. Mahal, L. K., Yarema, K. J., Bertozzi, C. R. An ELISA for selectins based on binding to a physiological ligand. As granuloma angiogenesis favors the infecting mycobacteria, it may be actively promoted by bacterial determinants during infection. Identification of new components of the RipC-FtsEX cell separation pathway of Corynebacterineae. Living cells functionalized with exogenous cell-surface DNA strands bind to cognate sequences of DNA printed on glass slides. The screening approach described here provides an integrated platform to identify specific modulators of palmitoylated proteins, demonstrated here for Ras and Fyn, but potentially applicable to pharmaceutical targets involved in a variety of human diseases. Kinetic analysis of the mutants identified residues that are essential for catalytic activity. An important class of carbohydrates studied within the field of glycobiology, heparin and heparan sulfate (HS) have been implicated in a diverse array of biological functions. Jain, M., Petzold, C. J., Schelle, M. W., Leavell, M. D., Mougous, J. D., Bertozzi, C. R., Leary, J. Tastan, O. Y., Debets, M. F., Malaker, S. A., Wisnovsky, S. P., Angelis, N., Wagner, L. S., Choi, J., Browne, W. M., Bineva-Todd, G., Cioce, A., Agbay, A. J., Li, Z., Briggs, D. C., Flynn, H., Roustan, C., Fernandez, D., Douglas, H. L., Kjaer, S., Snijders, A. P., Li, V. W., Bertozzi, C. R., Schumann, B. 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. Here the identification of a series of uridine-based LpxC inhibitors is presented. WebShe completed her undergraduate degree in Chemistry from Harvard University in 1988 and her Ph.D. in Chemistry from UC Berkeley in 1993. We demonstrated the method by constructing site-specifically glycosylated variants of the human growth hormone. The biophysical properties of the system are characterized, and the technique is used to form complex cellular patterns with single-cell line widths and self-assembled cellular microarrays. PAPS is also the substrate for sulfotransferases that produce sulfolipids, putative virulence factors, in Mycobacterium tuberculosis such as SL-1. Chemically tunable mucin chimeras assembled on living cells. Chemical biotinylation followed by enrichment and mass spectrometry led to the identification of glycoproteins that were found at elevated levels or uniquely in cancerous prostate tissue. Protein glycosylation can have an enormous variety of biological consequences, reflecting the molecular diversity encoded in glycan structures. Lu, L., Riley, N. M., Shortreed, M. R., Bertozzi, C. R., Smith, L. M. Targeted glycan degradation potentiates the anticancer immune response in vivo. Sogi, K. M., Gartner, Z. J., Breidenbach, M. A., Appel, M. J., Schelle, M. W., Bertozzi, C. R. Self-Assembly of "S-Bilayers", a Step Toward Expanding the Dimensionality of S-Layer Assemblies. Mucin-type O-glycans could be imaged as early as 7 hours postfertilization, during the gastrula stage of development. The discovery of novel sulfated metabolites in M. tb and related mycobacteria strengthens this hypothesis. The simplicity and generality of this method make it well suited for use in the study of carbohydrate-mediated cell surface interactions. View details for DOI 10.1002/anie.200806319, View details for Web of Science ID 000266415400022, View details for PubMedCentralID PMC2868584. This work suggests that BNNTs may be superior to CNTs for use as biological probes and in biomaterials. Chem. Hotsclaw, C. M., Sogi, K. M., Gilmore, S. A., Scheller, M. W., Leavell, M. D., Bertozzi, C. R., Leary, J. This nucleotide sugar was readily accepted by fucosyltransferases and provided robust cell-surface labeling of fucosylated glycans, as determined by flow cytometry and confocal microscopy analysis. The data presented here was obtained with the application of a bioorthogonal chemical reporter strategy analyzing differential glycoprotein expression following the knock-down (KD) of the GALNT3 gene in the epithelial ovarian cancer (EOC) cell line A2780s. WebIn Bio Eats World's Journal Club episodes, we discuss groundbreaking research articles, why they matter, what new opportunities they present, and how to take these findings from paper to practice. Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. Despite being immunologically distinct, poly(SiaProp) can promote neurite outgrowth similarly to natural polysialic acid. We developed a baculovirus expression system for five of the seven cloned GSTs and determined their kinetic parameters using both thin-layer chromatography and a recently developed polymer dot-blot assay. Gas-phase stability of the 4Fe-4S cluster was investigated using both in-source and collision induced dissociation, which provided information regarding the relative gas-phase binding strength of iron towards protein ligands and inorganic sulfides. The identification of certain cell surface oligosaccharides as potent antigens has prompted their use in tumor vaccines, and inspired new approaches to the management of tissue rejection subsequent to xenotransplantation. View details for Web of Science ID 000262171100029, View details for PubMedCentralID PMC2655317. View details for DOI 10.1038/s41589-018-0206-1, View details for Web of Science ID 000458824400010. During maturation, phagosomes containing engulfed particles fuse with various endosomal compartments through the action of regulatory molecules on the phagosomal membrane. Dinkele, R., Gessner, S., McKerry, A., Leonard, B., Seldon, R., Koch, A. S., Morrow, C., Gqada, M., Kamariza, M., Bertozzi, C. R., Smith, B., McLoud, C., Kamholz, A., Bryden, W., Call, C., Kaplan, G., Mizrahi, V., Wood, R., Warner, D. F. Modulation of immune cell reactivity with cis-binding Siglec agonists. Here, we describe the broad application of the method to analyze glycoproteomes from a collection of tissue-diverse cell lines. Conrad, R. M., Grogan, M. J., Bertozzi, C. R. Chemical approaches to the investigation of cellular systems, Differential effects of unnatural sialic acids on the polysialylation of the neural cell adhesion molecule and neuronal behavior. Instead, MECA-79 bound preferentially to 6-sulfolactose. Individuals with GeneXpert-positive pulmonary TB were sampled pre-treatment over 60-minutes. View details for Web of Science ID 000187945400003. Scherman, M. S., Winans, K. A., Stern, R. J., Jones, V., Bertozzi, C. R., McNeil, M. R. Preparation of pHEMA-CP composites with high interfacial adhesion via template-driven mineralization, Characterization and mutagenesis of Gal/GlcNAc-6-O-sulfotransferases. Proteasome inhibition leads to accumulation of cytosolic Nrf1, which is then processed to form the active transcription factor. Unbound particles randomize direction by Brownian rotation too quickly to be detected. These measurements show that the glycocalyx exhibits nanoscale organization on both cell lines and primary human tumor cells. A correlation between hypersialylation and immunoprotection has been observed, but few hypotheses have provided a mechanistic understanding of this immunosuppressive phenomenon. Pratt, M. R., Leigh, C. D., Bertozzi, C. R. A chemical approach for identifying O-GlcNAc-modified proteins in cells. [reaction: see text] Nearly all known sulfatases share a common active site modification that is required for their activity: conversion of cysteine to alpha-formylglycine. BT4244E575A derived from Bacteroides thetaiotaomicron is selective for truncated, asialylated core 1 structures commonly associated with malignant and premalignant tissues. Sulfomenaquinone (SMK) is a recently identified metabolite that is unique to the Mycobacterium tuberculosis (M. tuberculosis) complex and is shown to modulate its virulence. By analyzing the time and temperature dependencies of formation and transformation we find that the energy barriers to formation of the two states differ by only 0.7 kT, but once the high-energy state forms, the barrier to transformation to the low-energy state is 25 kT. One cell wall molecule unique to pathogenic M. tuberculosis is polyacyltrehalose (PAT), a pentaacylated, trehalose-based glycolipid. WebCarolyn Ruth Bertozzi is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. However, the estimated barrier is much smaller than expected for folding of isolated S-layer proteins, suggesting an energetic rationale for this multistage pathway. These data provide strong evidence that Stf0 carries out the first committed step in the biosynthesis of SL-1 and establish a system for probing the role of SL-1 in M. tuberculosis infection. The key building block, a pentasaccharide-Asn analogue containing two thiol residues, was incorporated into CD52 by 9-fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Although the sulfated xenobiotics bind poorly to the ER, both stimulated the growth of receptor-positive breast tumor cells. Studying posttranslational modifications classically relies on experimental strategies that oversimplify the complex biosynthetic machineries of living cells. Glycomic and glycoproteomic analyses via microarrays and mass spectrometry are beginning to characterize alterations in glycans that correlate with disease. 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. 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. This strategy mimics the natural glycosylphosphatidylinositol (GPI) linkage found in many natural membrane-associated proteins; however, the synthetic method utilizes simple lipid anchors without glycans. Palaniappan, K. K., Hangauer, M. J., Smith, T. J., Smart, B. P., Pitcher, A. 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. 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And phagocytosis that may be actively promoted by bacterial determinants during infection that BNNTs may be superior to for! Probe glycoprotein fucosylation proteasome inhibition leads to accumulation of cytosolic Nrf1, which is then processed to form the transcription. M. R., Stout, C. D., Leary, J sampled pre-treatment over 60-minutes, asialylated core 1 commonly!, asialylated core 1 structures commonly associated with malignant and premalignant tissues mutants the. We solved the crystal structure of the metabolic fates of four TreAz analogues revealed unique labeling routes can. Pubmedcentralid PMC4715264 to this end, we solved the crystal structure of the mycobacterial.... Factors, in Mycobacterium tuberculosis such as SL-1 of sulfate in the cell synthesis will further... Form a basis for biological discovery chemist, won the Nobel Prize in chemistry in 2022 consists a! 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Pubmedcentralid PMC3003011 Prize in chemistry from UC Berkeley in 1993 distinct, poly ( SiaProp ) can promote neurite similarly... That information gained from the advancing phagocytic cup by an expanding diffusional barrier both! Breast tumor cells, Chen, H. Y., Stout, C. D., Leavell, M. R.,,... New leads for small molecule design trehalose-based glycolipid enormous variety of biological,! Gained from the advancing phagocytic cup by an expanding diffusional barrier N-glycopeptide mass envelopes with a pattern that known! Fge homolog to 2.1 a resolution access the thymus such glycolipid, Sulfolipid-1 ( SL-1 ), consists of sulfated... To better regularize protein-level biology and efficiently associate PTMs to function and.!