Glycopeptide-bound glycans observed by IsoTaG were found to be comparable to released N-glycans identified by permethylation analysis. Harland, C. W., Botyanszki, Z., Rabuka, D., Bertozzi, C. R., Parthasarathy, R. Crosslinking Studies of Protein-Protein Interactions in Nonribosomal Peptide Biosynthesis. 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. Here we report two engineered aminoacyl-tRNA synthetases for mammalian bioorthogonal labeling: a tyrosyl ( ScTyrY43G) and a phenylalanyl ( MmPheT413G) tRNA synthetase that incorporate azide-bearing noncanonical amino acids specifically into the nascent proteomes of host cells. A chemical approach to unraveling the biological function of the glycosylphosphatidylinositol anchor. The cysH mutant was also susceptible to peroxynitrite and hydrogen peroxide in vitro. Here we explored their effect on corneal surface glycosylation using a metabolic label, tetra-acetylated N-azidoacetylgalactosamine (Ac4GalNAz). In some cases, the functional significance of disease-associated changes in glycosylation has been revealed. 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 DOI 10.1073/pnas.1201504109, View details for Web of Science ID 000307551700033, View details for PubMedCentralID PMC3420203. A computational model predicted that these glycoproteins would influence transmembrane receptor spatial organization and function. A., Sun, J., Iram, T., Bonanno, L., Li, L., Lee, D. P., Morgens, D. W., Yang, A. C., Shuken, S. R., Gate, D., Scott, M., Khatri, P., Luo, J., Bertozzi, C. R., Bassik, M. C., Wyss-Coray, T. Towards Mycobacterium tuberculosis detection at the point-of-care: solvatochromic probes permits the detection of mycobacteria within minutes, Orthogonal enzyme/substrate engineering to profile biological substrates of glycosyltransferases, Glyco-immune modulation in the tumor microenvironment, Formylglycine-generating enzyme binds substrate directly at a mononuclear Cu(I) center to initiate O-2 activation. a nanoscience research center at Lawrence Berkeley National Laboratory. Protein modification by O-linked -N-acetylglucosamine (O-GlcNAc) is a critical cell signaling modality, but identifying signal-specific O-GlcNAcylation events remains a significant experimental challenge. View details for DOI 10.1038/NCHEMBIO.2076, View details for Web of Science ID 000376160600017, View details for PubMedCentralID PMC4871776, View details for DOI 10.1021/acscentsci.6b00102, View details for PubMedCentralID PMC4850509. Although their biochemical properties are similar in vitro, the enzymes have distinct glycoprotein substrate preferences in vivo. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed for direct covalent modification of biomolecules with probes in the mouse, an important model organism for studies of human disease. The cyclooctynes tested displayed various labeling efficiencies that likely reflect the combined influence of intrinsic reactivity and bioavailability. Metabolically labeled glycoproteins are then tagged using Click chemistry and enriched with an isotopic recoding biotin probe. Thus, choice of enrichment strategy has profoundimplications on experimental outcomes. 1-68A and a 2-dehydroxy analogue, 1-68Aa, inhibit several purified LpxC orthologues. 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. The optimal configuration of sulfate esters on the N-acetyllactosamine (Galbeta1-->4GlcNAc) core of sulfosialyl-Le(X), however, remains unsettled. Sequential assembly of the septal cell envelope prior to V snapping in Corynebacterium glutamicum. We introduced an exogenous GlcNAc salvage pathway into yeast, allowing cells to metabolize GlcNAc provided as a supplement to the culture medium. [40] It focuses on biotechnologies for at-home diagnoses for type 1 diabetes, HIV, and other diseases. The Nobel Prize in Chemistry 2022. Here, we sought to define if uncharacterized sialidases would provide distinct paradigms in sialic acid biochemistry. Bioinformatic analysis of the Mtb genome suggests the presence of a CysQ homologue encoded by the gene Rv2131c. To elucidate the important sites of sulfation on Le(x) with respect to L-selectin recognition, we have synthesized six sulfated Le(x) analogs and determined their abilities to block binding of a recombinant L-selectin-Ig chimera to immobilized GlyCAM-1. Both normal and cancerous prostate tissues were sliced and cultured in the presence of the azide-functionalized sialic acid biosynthetic precursor Ac4 ManNAz. The technique of metabolic oligosaccharide engineering has been used to disrupt glycan biosynthesis, chemically modify cell surfaces, probe metabolic flux inside cells, and to identify specific glycoprotein subtypes from the proteome. View details for DOI 10.1073/pnas.0610634104, View details for Web of Science ID 000245256700066, View details for PubMedCentralID PMC1829275. The GPI-protein analogs also diffused freely in cellular membranes. Appel, M. J., Meier, K. K., Lafrance-Vanasse, J., Lim, H., Tsai, C., Hedman, B., Hodgson, K. O., Tainer, J. Although hundreds of proteins are known to be modified by O-GlcNAc, a strict amino acid consensus sequence for OGT has not been identified. Using an Orbitrap Fusion Tribrid mass spectrometer, we identified 699 intact glycopeptides from 192 glycoproteins. 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. However, the resulting C=N linkages are susceptible to hydrolysis under physiologically relevant conditions, which limits the utility of such conjugates in biological systems. A functional domain of the M. tuberculosis CysC protein was cloned and expressed in E. coli, confirming the ability of this organism to make PAPS. A., Gray, M. A., Bertozzi, C. R., Rabuka, D., Bassik, M. C. Quantitative super-resolution microscopy of the mammalian glycocalyx. Here we present the design, preparation, and characterization of self-assembling functional bolaamphiphilic polydiacetylenes (BPDAs) inspired by nature's strategy for membrane stabilization. [86] Her maternal grandparents were from Nova Scotia, Canada. 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. Exact mass measurements showed that S881 is highly unsaturated, tandem mass spectrometry indicated a polyisoprene-derived structure, and characterization of synthetic structural analogs confirmed that S881 is a previously undescribed sulfated derivative of dihydromenaquinone-9, the primary quinol electron carrier in M. tuberculosis. In this work, we undertook a mechanistic study of the Staudinger ligation with a focus on factors that affect reaction kinetics and on the identification of intermediates. Mucin biopolymers and long-chain polysaccharides within the glycocalyx can generate entropic forces that favor or disfavor the projection of spherical and finger-like extensions from the cell surface. Formylglycine generating enzyme (FGE) recognizes a pentapeptide consensus sequence, CxPxR, and it specifically oxidizes the cysteine in this sequence to an unusual aldehyde-bearing formylglyine. Czlapinski, J. L., Schelle, M. W., Miller, L. W., Laughlin, S. T., Kohler, J. J., Cornish, V. W., Bertozzi, C. R. Structural Characterization of a Novel Sulfated Menaquinone produced by stf3 from Mycobacterium tuberculosis. Fluorescent probes designed for activation by bioorthogonal chemistry have enabled the visualization of biomolecules in living systems. Her recent efforts include synthesis of chemical tools to study cell surface sugars called glycans and how Acute Modulation of Mycobacterial Cell Envelope Biogenesis by Front-Line Tuberculosis Drugs. View details for DOI 10.1073/pnas.0700567104, View details for Web of Science ID 000246599900007, View details for PubMedCentralID PMC1895932. Sialic acid is a major determinant of carbohydrate-receptor interactions in many systems pertinent to human health and disease. Ligation of synthetic lipids with designed anchor structures to proteins was performed using native chemical ligation (NCL) of a C-terminal peptide thioester and an N-terminal cysteine lipid. There is urgent need for new therapeutic targets and a better understanding of EOC initiation and progression. View details for DOI 10.1021/jacs.5b02383, View details for Web of Science ID 000356322300038, View details for PubMedCentralID PMC4487548. By mutating catalytic residues of two such enzymes, we engineered mucin-selective binding agents with retained glycoform preferences. 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. Atoms out of Blobs: CryoEM Takes the Nobel Prize in Chemistry. 2016 by John Wiley & Sons, Inc. View details for DOI 10.1002/9780470559277.ch150185, View details for PubMedCentralID PMC4809415. WebBertozzi is a professor of Humanities and Sciences, and of Chemical and Systems Biology and of Radiology. 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. These studies yield insight into the biosynthesis and dynamics of glycans in the enveloping layer during embryogenesis and provide a platform for imaging other biomolecular targets by microinjection of appropriately functionalized biosynthetic precursors. We conclude that Rv3406 is an iron and -ketoglutarate-dependent sulfate ester dioxygenase that has unique substrate specificity that is likely distinct from other Mtb sulfatases. Deletion of CysH from M. smegmatis afforded a cysteine and methionine auxotroph consistent with a metabolic branch point centered on APS. Oligosaccharides on proteins and lipids play central roles in human health and disease. Yet, a mechanistic understanding of how O-GlcNAc functions in T cell activation remains elusive, partly because of the difficulties in mapping and quantifying O-GlcNAc sites. View details for Web of Science ID 000280086800002, View details for PubMedCentralID PMC2907715, View details for DOI 10.1016/j.cplett.2010.04.067, View details for Web of Science ID 000279368000001. ( Bertozzi Aldehyde- and ketone-functionalized proteins are appealing substrates for the development of chemically modified biotherapeutics and protein-based materials. Kiick, K. L., Saxon, E., Tirrell, D. A., Bertozzi, C. R. An inhibitor of the human UDP-GlcNAc 4-epimerase identified from a uridine-based library: A strategy to inhibit O-linked glycosylation, Homogeneous glycopeptides and glycoproteins for biological investigation. [85] Her father was of Italian descent. View details for DOI 10.1073/pnas.0911247107, View details for Web of Science ID 000275131100011, View details for PubMedCentralID PMC2840165. After subsequent injection with cyclooctyne reagents, glycoconjugate labeling was observed on isolated splenocytes and in a variety of tissues including the intestines, heart, and liver, with no apparent toxicity. The artificial receptor enhanced adenoviral vector binding and gene transfer to cells that are relatively resistant to adenovirus infection. Finally, we showed that BNNTs can deliver DNA oligomers to the interior of cells with no apparent toxicity. This concise motif can be installed within heterologous proteins as a genetically encoded "aldehyde tag" for site-specific labeling with aminooxy- or hydrazide-functionalized probes. View details for DOI 10.1073/pnas.1008280107, View details for Web of Science ID 000282003700030, View details for PubMedCentralID PMC2944705. Directed proteomics applies mass spectrometry analysis to a subset of information-rich proteins. This suggests that post-translational myristoylation of caspase-cleaved proteins represents a novel mechanism widely used to regulate cell death. Baskin, J. M., Dehnert, K. W., Laughlin, S. T., Amacher, S. L., Bertozzi, C. R. Rapid and selective detection of fatty acylated proteins using omega-alkynyl-fatty acids and click chemistry. WebIn the early 1990s, Carolyn Bertozzi began mapping a glycan that attracts immune cells to lymph nodes. We report the synthesis of an alpha-formylglycine building block suitable for Fmoc-based solid-phase peptide synthesis. Hang, H. C., Yu, C., Pratt, M. R., Bertozzi, C. R. Detection of bacteria in suspension by using a superconducting quantum interference device. View details for DOI 10.1038/NCHEMBIO.1388, View details for Web of Science ID 000328854900013. Lastly, DMN-Tre labeled Mtb in TB-positive human sputum samples comparably to auramine staining, suggesting that this operationally simple method may be deployable for TB diagnosis. 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 View details for Web of Science ID 000430563200441. These results show that CysH is important for Mtb protection during the chronic infection phase, and that resistance to nitrosative and oxidative stress may be the mechanism of this protection. Taken together these results suggest that: (a) the relative content of O-glycans and intragranular anionic groups is crucial for protein diffusion through the intragranular meshwork; (b) protein-protein, rather than carbohydrate-mediated, interactions are responsible for binding of SHGFP-MUC5AC/CK to the immobile fraction, although the degree of matrix O-glycosylation and sialylation affects such interactions; (c) intragranular organization does not depend on covalent multimerization of mucins or the presence of native disulfide bonds in the intragranular mucin/proteins, but rather on specific protein-mediated interactions that are important during the early stages of mucin matrix condensation; (d) alterations of the intragranular matrix precede granule discharge, which can be partial and, accordingly, does not necessarily involve the disappearance of the granule. Using this procedure, we found that the rate constant for the cycloaddition reaction of DIFBO with an azide exceeds those for difluorinated cyclooctyne (DIFO) and dibenzocyclooctyne (DIBO). Applications to the visualization of cellular glycans and enrichment of glycoproteins for proteomic analysis are described. Stanford University biochemist Carolyn Bertozzi is a highly admired scientist, entrepreneur, and advocate for diversity, particularly for LGBTQ+ people. 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. Islet autoantibodies are predominantly measured by radioassay to facilitate risk assessment and diagnosis of type 1 diabetes. Here we demonstrate that a methionine surrogate, azidohomoalanine, is activated by the methionyl-tRNA synthetase of Escherichia coli and replaces methionine in proteins expressed in methionine-depleted bacterial cultures. Z., Uttamapinant, C., Poloukhtine, A., Baskin, J. M., Codelli, J. 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. Bioorthogonal tools enable cell-type-specific proteomics, a prerequisite to understanding biological processes in multicellular organisms. Here, we report a system for conditional activation of Golgi-resident sulfotransferases using a chemical inducer of dimerization. Though not directly subject to mutation, we can determine glycan structure-function relationships by synthesizing defined glycoconjugates or by altering natural glycosylation pathways. Four derivatives were experimentally verified in model reactions, and one, a 4-azidonaphthylfluorescein analogue, was further shown to label alkyne-functionalized proteins in vitro and glycoproteins on cells with excellent selectivity. Here, we systematically explore the advantages and disadvantages of conventional HCD, sceHCD, ETD, and EThcD for intact glycopeptide analysis and determine their suitability for both N- and O-glycoproteomic applications. The Gal/GalNAc/GlcNAc-6-O-sulfotransferases (GSTs) are a recently discovered family of carbohydrate sulfotransferases that share significant sequence homology at the amino acid level and mediate a number of different biological processes such as leukocyte adhesion at sites of chronic inflammation. 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