Isotopic recoding is achieved via metabolic incorporation of a defined mixture of N-acetylglucosamine isotopologs into N-glycans. More broadly, our method will enable the discovery of signal-specific O-GlcNAcylation events in a wide array of experimental contexts. 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). This bifunctional microelectrode array is demonstrated for the pH monitoring and differentiation of primary T cells and Jurkat T lymphoma cells. However, because they are internalized within hours, these glycopolymers could not be employed to probe processes that occur on longer time scales. Increased levels of circulating saturated free fatty acids, such as palmitate, have been implicated in the etiology of type II diabetes and cancer. Recently, the ability to modify monosaccharide structures within cellular glycans through metabolic processes has offered a new avenue for biological studies. Despite their importance, few N-glycosites have been experimentally mapped in the Saccharomyces cerevisiae proteome. Phagocytosis is initiated by lateral clustering of receptors, which in turn activates Src-family kinases (SFKs). Yet, our understanding of the invivo ligands and function for most lectins is still incomplete. Tests against related enzymes confirmed the compound's specificity for the UDP-GlcNAc 4-epimerase. 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. The antibodies recognized cells that were fed the unnatural biosynthetic precursor, and were capable of directing complement-mediated lysis.Structural alteration of sialic acids replaces a tolerized self-antigen with an antigenic determinant. Islet autoantibodies are predominantly measured by radioassay to facilitate risk assessment and diagnosis of type 1 diabetes. View details for DOI 10.1021/acs.chemrev.6b00023, View details for Web of Science ID 000389962700001, View details for PubMedCentralID PMC5327817, View details for DOI 10.1021/acscentsci.6b00341, View details for PubMedCentralID PMC5126708. We present IsoTaG, a mass-independent chemical glycoproteomics platform for characterization of intact, metabolically labeled glycopeptides at the whole-proteome scale. The structural identification of the fragments relied on the use of a variety of radiolabeled sugar precursors, further chemical and enzymatic hydrolysis, and high-pH anion-exchange chromatography analysis. B cell glycoproteins were robustly labeled with GalNAz but T cell glycoproteins were not, suggesting fundamental differences in glycosylation machinery or metabolism. Applications to the visualization of cellular glycans and enrichment of glycoproteins for proteomic analysis are described. Thus, sialylation of H. ducreyi LOS can be modulated with respect to the structure of the terminal sialic acid residue and the extent to which the LOS acceptor is modified by supplying the bacteria with various sialic acid analogs. View details for DOI 10.1021/acs.analchem.0c02950. DMN-Tre labeling enabled the rapid, no-wash visualization of mycobacterial and corynebacterial species without nonspecific labeling of Gram-positive or Gram-negative bacteria. This technique, which is described in detail, provides a direct measurement of the energy that is released nonradiatively following photostimulation, and can therefore be used to indirectly determine the amount of energy released via luminescent pathways. B., Stein, G. S., Ayers, D. C., Bertozzi, C. R. Chemical Approaches To Perturb, Profile, and Perceive Glycans, PapA3 Is an Acyltransferase Required for Polyacyltrehalose Biosynthesis in Mycobacterium tuberculosis. The availability of this new protocol greatly expands the applicability of the DNA-based attachment strategy for the generation of artificial tissues and the incorporation of living cells into device settings. Bhat, R., Belardi, B., Mori, H., Kuo, P., Tam, A., Hines, W. C., Le, Q., Bertozzi, C. R., Bissell, M. J. N-Acetylmannosamine (ManNAc) is the first committed intermediate in the sialic acid biosynthetic pathway; thus, the mechanisms that control intracellular ManNAc levels are important regulators of sialic acid production. Cells were decorated with biotin through selective conjugation to ketone groups, and selectively killed in the presence of a ricin A chain-avidin conjugate. This imaging approach should further our understanding of basic metabolic processes and pathological alterations in multiple disease models. View details for Web of Science ID 000089664300011, View details for Web of Science ID 000089432300004. O-Linked -N-acetylgalactosamine (O-GalNAc) glycans constitute a major part of the human glycome. In eukaryotic sulfatases, an active site cysteine residue is oxidized to the aldehyde-containing C(alpha)-formylglycine residue by the formylglycine-generating enzyme (FGE). [reaction: see text] Here we report a novel modification of our previously reported "Staudinger ligation" that generates an amide bond from an azide and a specifically functionalized phosphine. [86] Her maternal grandparents were from Nova Scotia, Canada. The 35S-labeled products are then captured on an appropriate membrane, taking advantage of their polymeric architecture. These compounds may provide new scaffolds for extension of existing LpxC-inhibiting antibiotics to target the UDP binding pocket. View details for DOI 10.1073/pnas.0700567104, View details for Web of Science ID 000246599900007, View details for PubMedCentralID PMC1895932. View details for DOI 10.1073/pnas.0601167103, View details for Web of Science ID 000239069400007, View details for PubMedCentralID PMC1502431. Two notable examples are the Staudinger ligation of azides and phosphines and the Cu(I)-catalyzed [3 + 2] cycloaddition of azides and alkynes ("click chemistry"). View details for DOI 10.1016/S0076-6879(06)15015-6, View details for Web of Science ID 000242168500015. Collectively, these chemical approaches are contributing great insight into the myriad biological functions of oligosaccharides. View details for Web of Science ID 000180258800025, View details for Web of Science ID 000181755600011, View details for Web of Science ID 000185102400018. Bertozzis graduate research focused on carbohydrate analog synthesis, intended for biological applications. These enzymes often comprise large families. Imaging analysis of glycan trafficking revealed dramatic reorganization of glycans on the second time scale, including rapid migration to the cleavage furrow of mitotic cells. We first report that a synthetic omega-alkynyl-palmitate analog can be readily and specifically incorporated into GAPDH or mitochondrial 3-hydroxyl-3-methylglutaryl-CoA synthase in vitro and reacted with an azido-biotin probe or the fluorogenic probe 3-azido-7-hydroxycoumarin using click chemistry for rapid detection by Western blotting or flat bed fluorescence scanning. These discoveries at the forefront of biological research have motivated the design of synthetic glycoconjugates as tools for the fundamental study of glycobiology and as candidates for future generations of therapeutic and pharmaceutical reagents. Studies showed that a bulky glycocalyx potentiates integrin mechanosignalling and tissue tension and promotes a mesenchymal, stem-like phenotype in GBMs. Third, omega-alkynyl-myristate is specifically incorporated into endogenous co- and posttranslationally myristoylated proteins. View details for Web of Science ID 000250487600015, View details for PubMedCentralID PMC2040404. We developed a novel universal MHC class II presentation assay based on a bio-orthogonal "clickable" antigen and showed that MHC class II presentation was disrupted by the inhibition of PIKfyve, which in turn resulted in reduced activation of CD4+ Tcells. Pathogenic bacteria have developed numerous mechanisms to survive inside a hostile host environment. Here, we discovered that osmotic stress stimulates a signaling network in Mycobacterium tuberculosis regulated by the eukaryotic-like receptor Ser/Thr protein kinase PknD. Leiden (2005); Iota Sigma Pi Agnes Fay Morgan Research Award (2004); Elected member of the American Academy of Arts and Sciences (2003); Irving Sigal Young Investigator Award of the Protein Society (2002); Fellow of the American Association for the Advancement of Science (2002); Donald Sterling Noyce Prize for Excellence in Undergraduate Teaching (2001); UC Berkeley Distinguished Teaching Award (2001); ACS Award in Pure Chemistry (2001); Merck Academic Development Program Award (2000); UC Berkeley Department of Chemistry Teaching Award (2000); Presidential Early Career Award in Science and Engineering (PECASE) (2000); MacArthur Foundation Award (1999); Camille Dreyfus Teacher-Scholar Award (1999); Arthur C. Cope Scholar Award (ACS) (1999); Joel H. Hildebrand Chair in Chemistry (1998-2000); Beckman Young Investigator Award (1998); Prytanean Faculty Award (1998); Glaxo Wellcome Scholar (1998); Research Corporation Research Innovation Award (1998); Office of Naval Research Young Investigator Award (1998); Horace S. Isbell Award in Carbohydrate Chemistry (ACS) (1997); Alfred P. Sloan Research Fellow (1997); Burroughs Wellcome New Investigator Award in Pharmacology (1997); Pew Scholars Award in the Biomedical Sciences (1996); Exxon Education Fund Young Investigator Award (1996); Camille and Henry Dreyfus New Faculty Award (1995); Bruce Mahan Teaching Award (1992); Outstanding Graduate Student Instructor Awards (1989, 1990); Thomas T. Hoopes Undergraduate Thesis Prize (1988); New England American Institute of Chemists Award (1988); Danforth Teaching Award (1987); Phi Beta Kappa (1987), Address:ChEM-H Building290 Jane Stanford Way, Room 235AStanford, CA 94305. The sulfotransferase incorporated greater than tenfold more sulfate into the disaccharide than the trisaccharide, indicating a requirement for a terminal GlcNAc. This enhancement occurs upon metabolic conversion of DMN-Tre to trehalose monomycolate and incorporation into the mycomembrane of Actinobacteria. We report a chemical approach for probing PG in vivo via metabolic labeling and bioorthogonal chemistry. Chang, P. V., Dube, D. H., Sletten, E. M., Bertozzi, C. R. Progress and challenges for the bottom-up synthesis of carbon nanotubes with discrete chirality, Identification of glycoproteins targeted by Trypanosoma cruzi trans-sialidase, a virulence factor that disturbs lymphocyte glycosylation. This system provides a unique framework with which to study the behavior of mucin-like macromolecules in a controlled, cell surface-mimetic environment. Here we studied the function of novel germline variants in CSF3R at amino acid N610. Mycobacterium tuberculosis synthesizes specific polyketide lipids that interact with the host and are required for virulence. A., Bertozzi, C. R. Biomimetic bonelike composites and novel bioactive glass coatings. This assay allows for direct product detection on the membrane, obviating excessive washing and elution steps endemic to other assays. Corrections? 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. 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. Front-line tuberculosis (TB) drugs have been characterized extensively invitro and invivo with respect to gene expression and cell viability. 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. Finally, the lipase inhibitor tetrahydrolipstatin disrupts Chp1 activity in M. tuberculosis, suggesting an avenue for perturbing SL-1 biosynthesis in vivo. The glycosylated polymers were end-functionalized with lipid groups and embedded into supported lipid bilayers where they interact with protein receptors in a structure-dependent manner. We used mass spectrometry to identify over 70 cell surface glycoproteins and biochemically validated CD146 and integrin beta-4, both of which are known to promote metastatic behavior. Here, we report a method that combines the metabolic incorporation of a cyclooctyne-functionalized sialic acid derivative with a ligation reaction of a fluorogenic tetrazine, allowing for the imaging of sialylated glycoconjugates within live zebrafish embryos. 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). Here we use combinatorial target-guided ligand assembly to discover the first known inhibitors of human TPST-2. Chen, X., Kis, A., Zettl, A., Bertozzi, C. R. Hierarchical assembly of model cell surfaces: Synthesis of mucin mimetic polymers and their display on supported bilayers. She is an elected member of the Institute of Medicine, National Academy of Sciences, and American Academy of Arts and Sciences. In this study, we developed a crosslinking assay, utilizing bioorthogonal probes compatible with carrier protein modification, for probing the protein interactions between COM domains of NRPS enzymes. Once released, HCBT and D-cysteine form firefly luciferin in situ, giving rise to a bioluminescent signal if and only if both chemical triggers proceed. View details for DOI 10.1074/jbc.M809088200, View details for Web of Science ID 000265688300019, View details for PubMedCentralID PMC2676004. Rabuka, D., Rush, J. S., dehart, G. W., Wu, P., Bertozzi, C. R. Cellular Microfabrication: Observing Intercellular Interactions Using Lithographically-Defined DNA Capture Sequences. Robinson, P. V., de Almeida-Escobedo, G., de Groot, A. E., McKechnie, J. L., Bertozzi, C. R. Chemical Lectinology: Tools for Probing the Ligands and Dynamics of Mammalian Lectins InVivo. Glycans are attractive targets for molecular imaging but have been inaccessible because of their incompatibility with genetically encoded reporters. After screening almost 8000 selected clones, we were able to isolate a single specific single chain Fv using two different selection strategies, one of which included elution with tyrosine sulfate. View details for DOI 10.1073/pnas.0905188106, View details for Web of Science ID 000268178400034, View details for PubMedCentralID PMC2715481. View details for DOI 10.1021/jacs.8b03074, View details for Web of Science ID 000435525500001, View details for DOI 10.3389/fmicb.2018.01117, View details for Web of Science ID 000433326300001. However, the lack of chemical tools to study mucin-type O-linked glycosylation has hindered our molecular understanding of O-linked glycans in many biological contexts. Dr. Carolyn R. Bertozzi Ph.D. serves as Independent Director of the Company. To overcome this barrier, we developed an artificial receptor based on expression of a novel sugar. Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. Woodruff, P. J., Carlson, B. L., Siridechadilok, B., Pratt, M. R., Senaratne, R. H., Mougous, J. D., Riley, L. W., Williams, S. J., Bertozzi, C. R. Syntheses of 6-sulfo sialyl Lewis X glycans corresponding to the L-selectin ligand "Sulfoadhesin", Deconvoluting the functions of polypeptide N-alpha-acetylgalactosaminyltransferase family members by glycopeptide substrate profiling. Within mammary epithelia, Gal-1 localized within nuclear Gemini bodies and drove epithelial invasiveness. The QC ligation thus brings novel chemical manipulations to the realm of bioorthogonal chemistry. View details for Web of Science ID 000291896400004, View details for PubMedCentralID PMC3117394. Overall, our findings provide a quantitative characterization of O-GlcNAc glycoproteins and their corresponding modification sites in primary human T cells, which will facilitate mechanistic studies into the function of O-GlcNAc in T cell activation. The unnatural sialic acid analog, N-levulinoyl sialic acid (SiaLev), was incorporated into cell surface glycoconjugates including PSA by the incubation of cultured neurons with the metabolic precursor N-levulinoylmannosamine (ManLev). This unique technique is currently being used to investigate the enzymatic mechanism of NodST and to identify sulfotransferase inhibitors. Carolyn R. Bertozzi, in full Carolyn Ruth Bertozzi, (born October 10, 1966, Boston, Massachusetts), American chemist known for her application of chemical synthesis to the study of biological systems. She coined the term bioorthogonal chemistry to describe the use of click reactionsquick, simple chemical reactions to study living cells. The caveat is that modified peptides would need to reliably contain only a single O-glycosite. View details for Web of Science ID A1997XK27100002. These results establish the foundation for further development of BPDA-based colorimetric sensors. The cyclooctynes tested displayed various labeling efficiencies that likely reflect the combined influence of intrinsic reactivity and bioavailability. [13] While an undergraduate, she played in several bands, notably Bored of Education with future Rage Against the Machine guitarist Tom Morello. Thus, cell assembly can be highly controlled, enabling the design of microtissues with defined cell composition and stoichiometry. These data complete the SL-1 biosynthetic pathway and corroborate a model in which lipid biosynthesis and transmembrane transport are coupled at the membrane-cytosol interface through the activity of multiple proteins, possibly as a macromolecular complex. [2] As of 2022, 12 awardees have subsequently become Nobel laureates; the most recent of those is Carolyn Bertozzi, who received the Nobel Prize the same year. Here we report that 5'-adenosinephosphosulphate reductase (CysH), an enzyme essential for the production of reduced-sulphur-containing metabolites, is critical for Mycobacterium tuberculosis (Mtb) survival in chronic infection phase in mice. She also later developed a click reaction called the strain-promoted alkyne-azide cycloaddition, which, unlike other click reactions involving azides and alkynes, did not require toxic copper ions for the azide to snap together with the alkyne and was highly effective for tracking glycans in live cells. In this work we used oligonucleotide microarrays to interrogate gene expression profiles associated with cell-biomaterial interactions. View details for DOI 10.1073/pnas.1114356109, View details for Web of Science ID 000302164200031, View details for PubMedCentralID PMC3323966. Here, we describe the computation-guided rational design of a cysteine- and lysine-containing 11-residue peptide sequence that reacts with 2-cyanobenzothiazole (CBT) derivatives. View details for DOI 10.1073/pnas.2012196117. Using azide-modified molecular precursors of sialic acids and copper-free click chemistry, we visualized the spatiotemporal dynamics of the sialome in live zebrafish embryos. By controlling the pools of 3'-phosphoadenosine 5'-phosphate (PAP) and 3'-phosphoadenosine 5'-phosphosulfate (PAPS), CysQ has the potential to modulate flux in the biosynthesis of essential sulfur-containing metabolites. 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. Concomitantly, a subpopulation of neural progenitor cells (NPCs) acquired an immature neuronal morphology and expressed early neuronal markers such as -III tubulin (TUJ1) and microtubule associated protein 2 (MAP2), phenotypes that took longer to manifest in the absence of OGT inhibition. Yarema, K. J., Mahal, L. K., Bruehl, R. E., Rodriguez, E. C., Bertozzi, C. R. Synthesis of an oxime-linked neoglycopeptide with glycosylation-dependent activity similar to its native counterpart. Identification of new components of the RipC-FtsEX cell separation pathway of Corynebacterineae. N-butanoylmannosamine blocked polysialylation of NCAM and significantly reduced neurite outgrowth comparable with enzymatic removal of PSA by endoneuraminidases. (1994) Biochemistry 33, 4830-4835] evidence is presented that (SO4-6)Gal beta 1-->4GlcNAc forms the core of a sulfated sialyl Lewis x structure that may comprise a recognition determinant on GlyCAM-1. Z. Multi-omics analysis of spatially distinct stromal cells reveals tumor-induced O-glycosylation of the CDK4-pRB axis in fibroblasts at the invasive tumor edge. In 2015 she became a professor of chemistry at Stanford University. Our results suggest that both Gal-6-SO(4) and GlcNAc-6-SO(4) may contribute to L-selectin recognition, either as components of sulfosialyl-Le(X) capping groups or in internal structures. Specific glycocalyx compositions can also induce plasma membrane instabilities to generate more exotic undulating and pearled membrane structures and drive secretion of extracellular vesicles. We provide evidence that conserved switch motifs in the G domain of CysN allosterically mediate interactions between the nucleotide binding sites. The cells' spatial arrangements and interconnectivities, both critical elements of higher-order function, derive from complex developmental programs in vivo and are often difficult or impossible to emulate in vitro. The kinetics of this reaction are of paramount importance for studies of dynamic processes, particularly in living subjects. In the latter case, we trace increased height to an effector gene, GALNT7. Using a high-throughput enzyme-linked lectin assay (ELLA), two inhibitors of murine ppGalNAcT-1 (K(I) approximately 8 microM) were identified that also inhibit several other members of the family. Luchansky, S. J., Goon, S., Bertozzi, C. R. Small molecule inhibitors of mucin-type O-linked glycosylation from a uridine-based library. O-glycopeptides with a modified N-terminal residue, such as those generated by OpeRATOR, present several potential benefits, perhaps the most notable being de facto O-glycosite localization without the need of glycan-retaining fragments in MS/MS spectra. By micropatterning IgG, the ligand of Fc receptors, we found that the barrier extended well beyond the perimeter of the receptor-ligand engagement zone. View details for DOI 10.1021/acscentsci.6b00070, View details for PubMedCentralID PMC4827488. Mckl, L. n., Pedram, K. n., Roy, A. R., Krishnan, V. n., Gustavsson, A. K., Dorigo, O. n., Bertozzi, C. R., Moerner, W. E. The Phosphoinositide Kinase PIKfyve Promotes Cathepsin-S-Mediated Major Histocompatibility Complex Class II Antigen Presentation. Bertozzi has over 600 publications on Web of Science; the most cited are: Bertozzi grew up in Lexington, Massachusetts, the daughter of the late Norma Gloria (Berringer) and William Bertozzi. Of novel germline variants in CSF3R at amino acid N610 11-residue peptide sequence that reacts with 2-cyanobenzothiazole ( ). On the membrane, obviating excessive washing and elution steps endemic to other assays assay for! 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