View details for Web of Science ID 000355248100027, View details for DOI 10.1021/acscentsci.5b00185, View details for PubMedCentralID PMC4827500. Studying posttranslational modifications classically relies on experimental strategies that oversimplify the complex biosynthetic machineries of living cells. The foundation focuses on curing NGLY1 deficiency through developing therapeutics that are efficient and inexpensive. A., Cox, J. S., Bertozzi, C. R. Introducing genetically encoded aldehydes into proteins. The synthesis utilizes a novel, orthogonally protected 3'-phosphoadenosine 5'-phosphate (PAP) derivative allowing the selective functionalization of the 5'-phosphate with a sulfate acceptor mimic. Using computational modeling, we designed the dendrimer scaffold and protein attachment point to resemble the native N-glycan architecture. View details for Web of Science ID A1995TD84500001. A., Bertozzi, C. R. Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation. For the glycopeptide substrates, ppGalNAc T10 exhibited a single large preference for Ser/Thr-O-GalNAc at the +1 (C-terminal) position relative to the Ser or Thr acceptor site. This review highlights changes in glycosylation associated with cancer and chronic inflammation and new therapeutic and diagnostic strategies that are based on the underlying glycobiology. Acute Modulation of Mycobacterial Cell Envelope Biogenesis by Front-Line Tuberculosis Drugs. WebCarolyn Ruth Bertozzi is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. Members of the Corynebacterineae, including Corynebacterium and Mycobacterium, have an atypical cell envelope characterized by an additional mycomembrane outside of the peptidoglycan layer. Secretory products can both diffuse, although very slowly, through the meshwork pores and interact noncovalently with the matrix. The most widely used CID, the natural product rapamycin and its relatives, is immunosuppressive due to interactions with endogenous targets and thus has limited utility in vivo. This approach bestows a gain-of-chemical-functionality modification on cells, where the products of individual glycosyltransferases can be selectively characterized or manipulated to understand glycan contribution to major physiological processes. View details for DOI 10.1073/pnas.0900717106, View details for Web of Science ID 000264522600009, View details for PubMedCentralID PMC2660766. A single GalNAc residue was incorporated at each glycosylation site using standard Fmoc-chemistry to achieve the first total synthesis of a mucin-type glycoprotein. 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. Recent progress in identifying and analyzing physiological selectin counter-receptors suggests new approaches to the design of ligands that bind to specific selectins. 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 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. A., Shrager, J. To use IsoTaG, cell culture samples are metabolically labeled with an azido- or alkynyl-sugar. 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. We report here a study of mycomembrane dynamics that was enabled by trehalose-fluorophore conjugates capable of labeling trehalose glycolipids in live actinomycetes. Chen, X., Wu, P., Rousseas, M., Okawa, D., Gartner, Z., Zettl, A., Bertozzi, C. R. DNA-barcode directed capture and electrochemical metabolic analysis of single mammalian cells on a microelectrode array. 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. Therefore, sulfation may increase the estrogenic potential of xenobiotics. View details for Web of Science ID 000180171800015. Armstrong, J. I., Verdugo, D. E., Bertozzi, C. R. Hydrogel polymers from alkylthio acrylates for biomedical applications. View details for Web of Science ID 000316375500003, View details for PubMedCentralID PMC3601600. Some awards of note include the Lemelson-MIT award for inventors, Whistler Award, Ernst Schering Prize, MacArthur Foundation Fellowship, the ACS Award in Pure Chemistry, Tetrahedron Young Investigator Award, and Irving Sigal Young Investigator Award of the Protein Society. Chemical or genetic disruption of NGLY1 activity results in the accumulation of misprocessed Nrf1 that is largely excluded from the nucleus. K chhai 2022-ngin tet-to Nobel Fa-hok Ching . Tests against related enzymes confirmed the compound's specificity for the UDP-GlcNAc 4-epimerase. Protein-based assemblies with ordered nanometer-scale features in three dimensions are of interest as functional nanomaterials but are difficult to generate. Cioce, A., Bineva-Todd, G., Agbay, A. J., Choi, J., Wood, T. M., Debets, M. F., Browne, W. M., Douglas, H. L., Roustan, C., Tastan, O. Y., Kjaer, S., Bush, J. T., Bertozzi, C. R., Schumann, B. LYTACs that engage the asialoglycoprotein receptor for targeted protein degradation. In this paper, an efficient enzyme kinetics assay for Stf0 using electrospray ionization (ESI) mass spectrometry is presented. Van de Bittner, G. C., Dubikovskaya, E. A., Bertozzi, C. R., Chang, C. J. The cyclooctynes tested displayed various labeling efficiencies that likely reflect the combined influence of intrinsic reactivity and bioavailability. Disruption of the papA3 gene from M. tuberculosis resulted in the loss of PAT from bacterial lipid extracts. Proteomics analyses were also performed and confirmed enrichment of plasma membrane proteins with some contamination from endoplasmic reticulum and other membranes. 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. Saxon, E., Armstrong, J. I., Bertozzi, C. R. Cell surface engineering by a modified Staudinger reaction, Tyrosine sulfation: a modulator of extracellular protein-protein interactions, Discovery of carbohydrate sulfotransferase inhibitors from a kinase-directed library. A., Rajaiah, G., Falck, J. R., Bertozzi, C. R., Berthiaume, L. G. Identification of palmitoylated mitochondrial proteins using a bio-orthogonal azido-palmitate analogue. The group was deliberately composed not only of individuals with a current research emphasis in the glycosciences, but also of many experts from other fields, who evinced a strong interest in being involved in the discussions. This work therefore extends the use of bioorthogonal labeling strategies to problems of clinical relevance. View details for DOI 10.1074/jbc.M405709200, View details for Web of Science ID 000223791500101, View details for Web of Science ID 000225338800003. An inhibitor of the UDP-GlcNAc 4-epimerase that synthesizes UDP-GalNAc, the donor initiating O-linked glycosylation, would be a powerful reagent for reversibly inhibiting O-linked glycosylation. T-cell progenitors originate in the bone marrow and are mobilized to the blood at regular intervals by unknown signals. Furthermore, we show that the biosynthesis of S881 relies on the universal sulfate donor 3'-phosphoadenosine-5'-phosphosulfate and a previously uncharacterized sulfotransferase, stf3. [8] Since 2021 she has been a member of the Accademia dei Lincei. Insects protect themselves against bacterial infection by secreting a battery of antimicrobial peptides into the hemolymph. Z. O-Pair Search with MetaMorpheus for O-glycopeptide characterization. View details for Web of Science ID 000171801100023. However, the mechanisms of impaired microglial homeostatic function and the cognitive effects of restoring this function remain unknown. She later refined the approach to improve its utility in cellular environments, facilitating research into interactions between biomolecules and into disease processes. 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. 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. Her recent efforts include synthesis of chemical tools to study cell surface sugars called glycans and how they affect diseases In particular, she showed that such reactions could be carried out inside living cells to map molecules and cell function, without disturbing normal cellular chemistry. Cholesterol Catabolism by Mycobacterium tuberculosis Requires Transcriptional and Metabolic Adaptations. View details for Web of Science ID 000264791600009, View details for PubMedCentralID PMC2657038. WebCarolyn Bertozzi (1966-ngin 10-ngiet 10-ngit ) he M-koet ke yit-chak fa-hok-k. The article will highlight recent approaches to thesynthesis of glycopeptide fragments bearing complex O-linkedglycans, as well as new strategies for the generation of full-lengthglycoproteins. 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. View details for DOI 10.1073/pnas.2012196117. Photoacoustic calorimetry combined with established absorption and fluorescence methodologies provides a complete arsenal for characterizing the photophysical properties of many systems. We evaluated a panel of four lectins (Soybean agglutinin (SBA), Wisteria floribunda lectin (WFL), Vicia villosa-B-4 agglutinin (VVA), and Helix pomatia agglutin (HPA)) with specificity for -N-acetylgalactosamine (-GalNAc), an epitope displayed on mucins overexpressed in many adenocarcinomas. Biochemistry in the context of a living cell or organism is complicated by many variables such as supramolecular organization, cytoplasmic viscosity, and substrate heterogeneity. However, what is lacking from this biochemical picture is how cells, tissues, and organisms interpret glycan patterns and translate this information into appropriate responses. Chemical syntheses of uniform glycoproteins and polymeric glycoprotein mimics have facilitated the study of individual glycoconjugates in the absence of glycan microheterogeneity. Together, localisation and association govern the assembly of complex glycans and thereby regulate interactions at the cell surface. Chang, P. V., Chen, X., Smyrniotis, C., Xenakis, A., Hu, T., Bertozzi, C. R., Wu, P. Quantitative Proteomic Profiling of Host-Pathogen Interactions: The Macrophage Response to Mycobacterium tuberculosis Lipids. View details for Web of Science ID 000256043200016, View details for PubMedCentralID PMC2711008. Because the parameters which govern this effect are well understood and are amenable to chemical modification, this knowledge may enable the rational development of more effective antibiotics against tuberculosis. 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. 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. 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. She joined Britannica in 2006 and Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree. I actually started as a premed. These measurements show that the glycocalyx exhibits nanoscale organization on both cell lines and primary human tumor cells. Andres, L. M., Blong, I. W., Evans, A. C., Rumachik, N. G., Yamaguchi, T., Pham, N. D., Thompson, P., Kohler, J. J., Bertozzi, C. R. Bioorthogonal Labeling of Human Prostate Cancer Tissue Slice Cultures for Glycoproteomics. View details for Web of Science ID 000251457800039, View details for PubMedCentralID PMC2654346. Some members of the family prefer previously gly co sylated peptides (ppGalNAc T7 and T10), whereas others are inhibited by neighboring gly co sy la tion (ppGalNAc T1 and T2). WebPrincipal Investigator. Living cells functionalized with exogenous cell-surface DNA strands bind to cognate sequences of DNA printed on glass slides. 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. Empty chamber samples were collected between patients as controls.The optimised RASC-2 protocol sampled a median of 258.4L (IQR: 226.9-273.6) of exhaled air per patient compared with 27.5L (IQR: 23.6-30.3) for RASC-1 (p<0.0001). The incorporation of noncanonical amino acids into recombinant proteins in Escherichia coli can be facilitated by the introduction of new aminoacyl-tRNA synthetase activity into the expression host. Now N-(4-pentynoyl)mannosamine can be used to metabolically label sialylated glycoproteins in living animals, enabling future identification of new biomarkers. 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. View details for Web of Science ID 000180258800025, View details for Web of Science ID 000181755600011, View details for Web of Science ID 000185102400018. We then demonstrated that in these microarrays, the glycopolymer ligands bind lectins according to the structures of their pendant glycans. Cell surface glycans govern numerous cell-cell interactions are therefore key determinants of multicellular biology. Isotopic recoding is achieved via metabolic incorporation of a defined mixture of N-acetylglucosamine isotopologs into N-glycans. Consequently, there is no obvious means to selectively monitor the behaviors of natural galectin ligands on live cell surfaces. A key tool in this study is the Staudinger ligation, a highly selective reaction between modified triarylphosphines and azides that produces an amide-linked product. In this Account, we focus on research in our laboratory that seeks to transform the study of glycan function from a challenge to routine practice. View details for Web of Science ID 000171204900005. These intact glycopeptides represent a total of eight sialylated glycan structures across 126 N- and 576 O-glycopeptides. Thus, we hypothesize that either MmpL8 transports molecules in addition to SL-1 that mediate host-pathogen interactions or the accumulation of SL(1278) in mmpL8 mutant cells interferes with other pathways required for growth during the early stages of infection. Conversely, unsialylated LacNAc glycans, enriched in the epithelial ducts, sequestered Gal-1 in the extracellular environment, ultimately attenuating invasive potential. Changes in their sulfation pattern and domain organization have been associated with different pathological situations such as viral infectivity, tumor growth, and metastasis. View details for Web of Science ID 000082564500003. 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. Bertozzi is a professor View details for Web of Science ID A1995TG85900001. Attachment via these "cell-adhesion barcodes" is rapid and specific, with close-packed arrays of cells forming within minutes. View details for Web of Science ID 000240465200023, View details for PubMedCentralID PMC3233198. A., Bertozzi, C. R. Compositional profiling of heparin/heparan sulfate using mass spectrometry: assay for specificity of a novel extracellular human endosulfatase. 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. We introduced an exogenous GlcNAc salvage pathway into yeast, allowing cells to metabolize GlcNAc provided as a supplement to the culture medium. However, their weak binding interactions do not correlate with the high-affinity binding interactions witnessed in vivo. Several protein lysine methyltransferases (PKMTs) modify histones to regulate chromatin-dependent cellular processes, such as transcription, DNA replication and DNA damage repair. 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. We fed cells an unnatural monosaccharide, a modified mannosamine that replaced the acetyl group with a levulinate group (ManLev). 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. Glycoproteins are typically expressed as mixtures of glycoforms, their oligosaccharides being generated by a template-independent biosynthetic process. 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. Grogan, M. J., Kaizuka, Y., Conrad, R. M., Groves, J. T., Bertozzi, C. R. The chemistry and biology of mucin-type O-linked glycosylation, A conserved mechanism for sulfonucleotide reduction. 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. We present a novel glycodendron prosthetic which can be site-selectively appended to recombinant proteins to create 'N-glycosylated' glycoprotein mimics. Peptides into the hemolymph ID A1995TG85900001 O-GlcNAc-modified proteins and the elucidation of the Accademia dei Lincei exogenous cell-surface strands. 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