Using this method, we identified 21 putative palmitoylated proteins in the rat liver mitochondrial matrix, a compartment not recognized for its content in palmitoylated proteins, and confirmed the palmitoylation of newly identified mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase. 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. Rabuka, D., Hubbard, S. C., Laughlin, S. T., Argade, S. P., Bertozzi, C. R. Chemical technologies for probing glycans, A role for sulfation-desulfation in the uptake of bisphenol A into breast tumor cells. Nevertheless, CD45 remained to be the main acceptor. Metabolic and bioorthogonal labeling methods have previously enabled the enrichment and identification of sialoglycoproteins from cultured cells and model organisms. Lim, H. C., Sher, J. W., Rodriguez-Rivera, F. P., Fumeaux, C. n., Bertozzi, C. R., Bernhardt, T. G. The mucin-selective protease StcE enables molecular and functional analysis of human cancer-associated mucins. View details for DOI 10.1073/pnas.1012864107, View details for Web of Science ID 000285521500020, View details for PubMedCentralID PMC3003011. and Kirk Schanze and Lee, {T. Randall} and Lutkenhaus, {Jodie L.} and David Kaplan and Christopher Jones and Carolyn Bertozzi and Laura Kiessling and Mulcahy, {Mary Beth} and Lindsley, {Craig W.} and Finn, {M. G.} and Blum, {Joel D.} and Prashant Kamat and About that time, she also began mapping a specific glycana type of carbohydrate typically found on the surface of cellsthat specializes in attracting immune cells toward the lymph nodes. Synthetic Siglec-9 Agonists Inhibit Neutrophil Activation Associated with COVID-19. The striking similarity of the desiccation resistance observed with TDM and the synthetic trehalose glycolipids, despite the variety of hydrophobic tail structures employed, suggests that interactions between the trehalose headgroup and surrounding molecules are the determining factor in dehydration protection. These data highlight the power of advanced imaging methods to provide molecular and functional insights into glycocalyx biology. These results establish the foundation for further development of BPDA-based colorimetric sensors. On this Wikipedia the language links are at the top of the page across from the article title. Progress in the identification and characterization of myristoylated proteins has been impeded by the long exposure times required to monitor incorporation of radioactive myristate into proteins (typically 1-3 months). A significant proportion (>45%) of the identified O-GlcNAc sites lie in close proximity to or coincide with a known phosphorylation site, supporting the potential for PTM crosstalk. In both leukocyte populations, the main proteins labeled were identified as different CD45 isoforms. Classic methods for monitoring glycans rely on molecular recognition with probe-bearing lectins or antibodies, but these techniques are not well suited to in vivo imaging. Despite being immunologically distinct, poly(SiaProp) can promote neurite outgrowth similarly to natural polysialic acid. Our results show that, like palmitate, incorporation of azido-palmitate occurred on mitochondrial proteins via thioester bonds at sites that could be competed out by palmitoyl-CoA. 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. Our results reveal that these transferases have unique peptide and glycopeptide preferences demonstrating their substrate diversity and their likely roles ranging from initiating transferases to filling-in transferases. 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. Riley, N. M., Bertozzi, C. R., Pitteri, S. J. Physical Principles of Membrane Shape Regulation by the Glycocalyx. View details for DOI 10.1073/pnas.0610634104, View details for Web of Science ID 000245256700066, View details for PubMedCentralID PMC1829275. View details for DOI 10.1021/acsomega.0c00071, View details for PubMedCentralID PMC7114878. Beam-type collisional activation, i.e., higher-energy collisional dissociation (HCD), has been a valuable approach, but stepped collision energy HCD (sceHCD) and electron transfer dissociation with HCD supplemental activation (EThcD) have emerged as potentially more suitable alternatives. This was confirmed by enzymatic assay of the partially purified enzyme with unnatural substrates. Living cells functionalized with exogenous cell-surface DNA strands bind to cognate sequences of DNA printed on glass slides. These stratergies for cell surface 'glycoform remodeling' promise to facilitate the investigation of carbohydrate mediated cell-cell interactions. The competitive inhibitors 2-bromopalmitate and 2-hydroxymyristate prevented incorporation of omega-alkynyl-palmitate and omega-alkynyl-myristate into palmitoylated and myristoylated proteins, respectively. The results from our study strongly suggest a rapid equilibrium random sequential Bi-Bi mechanism for Stf0 with formation of a ternary complex intermediate. Portraits of the 2022 Nobel laureates in Chemistry Carolyn R. Bertozzi (L), Morten Meldal (C) and K. Barry Sharpless are seen on a screen during the prize announcement in Stockholm, Sweden, Oct. 5, 2022. filexlib. Despite decades of accumulated knowledge about proteins and their post-translational modifications (PTMs), numerous questions remain regarding their molecular composition and biological function. Carolyn Bertozzi (Image credit: American Chemical Society) View details for Web of Science ID 000171801100023. 5 '-adenosinephosphosulfate lies at a metabolic branch point in mycobacteria. Azido sugars are fed to cells or organisms and integrated by the glycan biosynthetic machinery into various glycoconjugates. Using these probes, chemoselective imaging of either H(2)O(2) or caspase 8 activity was performed in vitro and in vivo. Presented herein is the synthesis and evaluation of a bisubstrate analogue designed to inhibit estrogen sulfotransferase. The rapid assembly of "core 1"and "core 3" O-linked glycopeptide mimetics was accomplished in this fashion. We designed synthetically tractable glycosylated polymers that possess rodlike extended conformations similar to natural mucins. In an emerging strategy, glycans are imaged by metabolic labeling with chemical reporters and subsequent ligation to fluorescent probes. The alkyl azide was then selectively derivatized with cyclo-octyne conjugates to various probes. These findings suggest that high mannose glycans are the major component of cell surface glycosylation with even terminal glucoses. This article contains raw and processed data related to research published in "Role of the polypeptide N-acetylgalactosaminyltransferase 3 in ovarian cancer progression: possible implications in abnormal mucin O-glycosylation" [1]. The enzymes that determine protein O-GlcNAcylation, O-GlcNAc transferase (OGT) and O-GlcNAcase (OGA), act on key transcriptional and epigenetic regulators, and both are abundantly expressed in the brain. View details for Web of Science ID 000264791600009, View details for PubMedCentralID PMC2657038. 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. The assay proceeds by transfer of 35S-labeled sulfate from [35S]-3(')-phosphoadenosine-5(')-phosphosulfate (PAPS) to the free amino groups of de-N-sulfated heparin (NDST-1), or the 6-hydroxyl groups of N-acetylglucosamine residues linked to a polyacrylamide scaffold (HEC-GlcNAc-6-ST). Furthermore, we demonstrate that the metabolic diversity of nature enables the use of naturally occurring functional groups that display inherent biocompatibility alongside abiotic components for organism-specific applications. View details for Web of Science ID 000222930600016. Carolyn Bertozzi. The presence of SiaLev groups on the neuronal cell surface did not impede neurite outgrowth or significantly affect the distribution of PSA on neuronal compartments. Here, we describe a chemical biology approach for unbiased, proteome-wide identification of novel PKMT substrates. We constructed a glycoprotein expression signature, which revealed that metastatic tumours upregulate expression of bulky glycoproteins. One cell wall molecule unique to pathogenic M. tuberculosis is polyacyltrehalose (PAT), a pentaacylated, trehalose-based glycolipid. View details for Web of Science ID 000452746700035, View details for Web of Science ID 000452746700102, View details for Web of Science ID 000460646301455, View details for DOI 10.1021/acscentsci.8b00740, View details for PubMedCentralID PMC6202648, View details for Web of Science ID 000448053200001. Such structural alterations to cell surface glycans can be used to probe carbohydrate-dependent phenomena. View details for DOI 10.1021/acs.analchem.0c02950. Additionally, we observe enhanced glycocalyx height in response to epithelial-to-mesenchymal transition and to oncogenic KRAS activation. These findings provide a platform for defining the molecular basis of SMK's role in M. tuberculosis pathogenesis. The efficacy of antimicrobial drugs against Mycobacterium tuberculosis, an intracellular bacterial pathogen, is generally first established by testing compounds against bacteria in axenic culture. A., Bertozzi, C. R. Biomimetic bonelike composites and novel bioactive glass coatings. Provocatively, these same processes are vital components of immune development and function. WebAbout Carolyn's Work. The polymers were designed to mimic native cell-surface mucin glycoproteins, which are defined by their dense glycosylation patterns and rod-like structures. Approximately one thousand proteins are annotated as being palmitoylated, and for some of these, including several oncogenes of the Ras and Src families, palmitoylation is indispensable for protein function. The novel rodlike polymers mimic the architecture of mucin glycoproteins and feature a phospholipid tail for membrane incorporation and a fluorescent optical probe for FLIC imaging situated at the opposite termini of the densely glycosylated polymeric backbones. The review discusses the significance of mucin-type O-linked glycosylation initiated by the polypeptide N-acetylgalactosaminyltransferases in biology and development of chemical tools to study these enzymes and their substrates. Interestingly, two sulfotransferase genes are highly similar to mammalian sulfotransferases, increasing the list of mycobacterial eukaryotic-like protein families. Previous reports have shown that synthetic DNA strands can be attached to the plasma membrane of living cells to equip them with artificial adhesion "receptors" that bind to complementary strands extending from material surfaces. View details for Web of Science ID A1997XK27100002. This work suggests that BNNTs may be superior to CNTs for use as biological probes and in biomaterials. Homogeneously glycosylated proteins are important targets for fundamental research and for biopharmaceutical development. 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. View details for Web of Science ID 000280227700012, View details for PubMedCentralID PMC2907714. Both the Staudinger ligation and the strain-promoted [3 + 2] cycloaddition using optimized cyclooctynes were effective for tagging azides on live cells. A goal of tissue engineering is to produce a scaffold material that will guide cells to differentiate and regenerate functional replacement tissue at the site of injury. These data show that the normal distribution of surface glycosylation requires IL-1R, but not MyD88, and is not sufficient to prevent bacterial binding. Bouchard, G., Garcia-Marques, F. J., Karacosta, L. G., Zhang, W., Bermudez, A., Riley, N. M., Varma, S., Mehl, L. C., Benson, J. Insects protect themselves against bacterial infection by secreting a battery of antimicrobial peptides into the hemolymph. CysQ, a 3'-phosphoadenosine-5'-phosphatase, is considered an important regulator of this pathway in plants, yeast, and other bacteria. Fine-tuning of glycan biosynthetic pathways is further accomplished by specific associations among glycosyltransferases. [12], Carolyn Bertozzi received her A.B. This study expands the repertoire of oncogenic mutations in CSF3R that are therapeutically targetable and provides insight into the function of glycans in receptor regulation. 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. Mucin biology has been difficult to study at the molecular level, in part, because methods to manipulate and structurally characterize mucin domains are lacking. 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. The loss of SL-1 (and SL(1278)) did not appear to affect bacterial replication or trafficking, suggesting that the functions of SL-1 are specific to human infection. Kinase inhibitors blocked growth of cells with an N610 mutation. Here we show that a stf0-deletion mutant exhibits augmented survival in human but not murine macrophages, suggesting that SL-1 negatively regulates the intracellular growth of Mtb in a species-specific manner. Northern blot analysis identified a single 5.5-kb ppGalNAc-T transcript. Thus, choice of enrichment strategy has profound implications on experimental outcomes. Baranov, M. V., Bianchi, F., Schirmacher, A., van Aart, M. A., Maassen, S., Muntjewerff, E. M., Dingjan, I., Ter Beest, M., Verdoes, M., Keyser, S. G., Bertozzi, C. R., Diederichsen, U., van den Bogaart, G. Making Glycoproteomics via Mass Spectrometry More Accessible to the greater Scientific Community. Specific labeling of biomolecules with biochemical and biophysical probes is a central element of proteomics research. Kramer, J. R., Onoa, B., Bustamante, C., Bertozzi, C. R. Systemic Fluorescence Imaging of Zebrafish Glycans with Bioorthogonal Chemistry. 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. View details for Web of Science ID 000257257100003, View details for PubMedCentralID PMC2663890. 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. These modified proteins integrated into the plasma membranes of a variety of mammalian cells and were internalized and directed to recycling endosomes similarly to GFP bearing a native GPI anchor. In addition, the general assay architecture should be readily applicable to high-throughput screens of other carbohydrate sulfotransferases. 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. 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). Current approaches offer a precision approaching that of genetic control. This imaging approach should further our understanding of basic metabolic processes and pathological alterations in multiple disease models. In these sulfur auxotrophs, heavy sulfate is channeled exclusively into sulfated metabolites. Examples from the past decade suggest that a promising strategy for bioorthogonal reaction development begins with an analysis of functional group and reactivity space outside those defined by Nature. Hammett analyses demonstrated that electron-donating substituents on the phosphine accelerate the overall reaction. To elevate the reactivities of cyclooctynes, two strategies, LUMO lowering through propargylic fluorination and strain enhancement through fused aryl rings, have been explored. She became an assistant professor at Berkeley in 1996 and a full professor of chemistry and molecular and cell biology in 2002. WebCarolyn Ruth Bertozzi is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. We determined the crystal structure of the apo Rv3406 sulfatase at 2.5 . Expansion of this toolkit, an effort that is already well underway, is an important objective for chemists and biologists alike. The difference in preferred substrates between L-selectin and MECA-79 may explain the variable activity of MECA-79 as an inhibitor of lymphocyte adhesion to high endothelial venules in lymphoid organs. View details for DOI 10.1038/s41589-019-0342-2, View details for Web of Science ID 000525055501242, View details for Web of Science ID 000516535000056. View details for Web of Science ID A1997WW72400006. The ability to rapidly and systematically vary the composition of these assemblies is a distinguishing feature of this methodology and may be applied to the study of other systems where composite binding determinants are important for high-affinity binding. Although theoretical predictions suggest that proteins follow these pathways as a result of fluctuations that create unstable dense-liquid states, microscopic studies indicate these states are long-lived. 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. The detection yield of viable Mtb improved from 43% (median 2 CFU, range: 1-14) to 95% (median 20.5 DMN-Trehalose positive bacilli, range: 2-155). Synthetic glycopolymers that emulate cell-surface mucins have been used to elucidate the role of mucin overexpression in cancer. Swarts, B. M., Holsclaw, C. M., Jewett, J. C., Alber, M., Fox, D. M., Siegrist, M. S., Leary, J. 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). Yap, M. C., Kostiuk, M. A., Martin, D. D., Perinpanayagam, M. A., Hak, P. G., Siddam, A., Majjigapu, J. R., Rajaiah, G., Keller, B. O., Prescher, J. 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). There is urgent need for new therapeutic targets and a better understanding of EOC initiation and progression. The resulting surfaces are then demonstrated to be able to capture up to three distinct types of living cells in specific locations. Through comparative analysis of screens with ADCs bearing different linkers, we show that a subset of late endolysosomal regulators selectively influence toxicity of noncleavable linker ADCs. Expression of the PknD substrate Rv0516c was highly induced by osmotic stress. After completing postdoctoral work at UCSF in the field of cellular immunology, she joined the UC Berkeley faculty in 1996. WebCarolyn Bertozzi, PhD. Xiao, H., Woods, E. C., Vukojicic, P., Bertozzi, C. R. Proteomic dataset for altered glycoprotein expression upon GALNT3 knockdown in ovarian cancer cells. 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. 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