The cell-surface repertoire can be expanded to include abiotic functionality through the biosynthetic introduction of unnatural sugars into cellular glycans, a process termed metabolic oligosaccharide engineering. Traditional spectrophotometric assays are not applicable to the NodST system since no shift in absorption accompanies sulfuryl group transfer. [22][23] While working with Rosen at UCSF, Bertozzi was able to modify the protein and sugar molecules in the walls of living cells so that the cells accept foreign materials such as implants. Hsiao, S. C., Crow, A. K., Lam, W. A., Bertozzi, C. R., Fletcher, D. A., Francis, M. B. The implications of the binary and ternary complexes observed by gas-phase noncovalent interactions in the mechanism of APS reduction are discussed. Harland, C. W., Botyanszki, Z., Rabuka, D., Bertozzi, C. R., Parthasarathy, R. Crosslinking Studies of Protein-Protein Interactions in Nonribosomal Peptide Biosynthesis. Immunization of mice with either BCG or DeltacysH followed by infection with the virulent M. tuberculosis Erdman strain demonstrated that DeltacysH can generate protection equivalent to that of the BCG vaccine. However, currently available agonists are heterogeneous glycoconjugates and polysaccharides from natural sources. The sulfur assimilation pathway is a key metabolic system in prokaryotes that is required for production of cysteine and cofactors such as coenzyme A. 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. In this paper, an efficient enzyme kinetics assay for Stf0 using electrospray ionization (ESI) mass spectrometry is presented. Applying IsoStamp, we were able to detect femtomole quantities of a single tagged protein from total mammalian cell lysates at signal-to-noise ratios as low as 2.5:1. Here we describe a strategy for exploiting trehalose metabolic pathways to label glycolipids in mycobacteria with azide-modified trehalose (TreAz) analogues. We use this framework to assess existing data and to ask the question, "How many distinct primary structures of proteins (proteoforms) are created from the 20,300 human genes?" During the past two years, significant progress has been made in the design and synthesis of carbohydrate-based inhibitors of selectins, receptors involved in the attachment of leukocytes to endothelial cells at sites of inflammation. A comparative study of bioorthogonal reactions with azides. Although global sulfatase activity was reduced in the mutant, a significant amount of residual sulfatase activity suggests the presence of FGE-independent sulfatases in this organism. View details for Web of Science ID A1994NH63300010. 135 amino acids) stem region and the presence of several important sequence motifs. Here, we demonstrate that recombinant proteins expressed in mammalian cells can be site-specifically modified by using a genetically encoded aldehyde tag. Omissions? View details for DOI 10.1128/AEM.01537-10, View details for Web of Science ID 000284310500026, View details for PubMedCentralID PMC2988590, View details for DOI 10.1002/cbic.201000419, View details for Web of Science ID 000284050000005, View details for PubMedCentralID PMC3069858, View details for DOI 10.1002/cbic.201000115, View details for Web of Science ID 000284050000006, View details for PubMedCentralID PMC3069857. Upon exposure to mycobacterial cell wall lipids, 166 macrophage proteins showed differential expression. A., Bertozzi, C. R. Synthesis of mono- and dideoxygenated alpha,alpha-trehalose analogs. Grabenstein, S., Barnard, K. N., Anim, M., Armoo, A., Weichert, W. S., Bertozzi, C. R., Parrish, C. R., Willand-Charnley, R. Systemic delivery of a targeted synthetic immunostimulant transforms the immune landscape for effective tumor regression. Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. Shes been out since the late 1980s, when being a lesbian could have jeopardized her career. Recently it was shown that the mucin GlyCAM-1, a secreted physiological ligand for L-selectin, is capped with sulfated derivatives of sialyl Lewis x [sLe(x): Sia alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc] and that sulfation is required for the high-affinity interaction between GlyCAM-1 and L-selectin. Enrichment of peptides derived from cytochrome c treated with the azide-containing cross-linker bis(succinimidyl)-3-azidomethyl glutarate (BAMG) shows several cross-link containing peptides. We used the CalFluor probes to image various alkyne-labeled biomolecules (glycans, DNA, RNA, and proteins) in cells, developing zebrafish, and mouse brain tissue slices. Here the identification of a series of uridine-based LpxC inhibitors is presented. summa cum laude in chemistry from Harvard University, where she worked with Professor Joe Grabowski on the design and construction of a photoacoustic calorimeter. View details for DOI 10.1073/pnas.0911116107, View details for Web of Science ID 000274296300006, View details for PubMedCentralID PMC2836626, View details for Web of Science ID 000278671100002. Mucin-type O-linked glycoproteins are involved in a variety of biological interactions in higher eukaryotes. Polysialyltransferases catalyze the glycosylation of the neural cell adhesion molecule (NCAM) with polysialic acid (PSA). A single multiwalled carbon nanotube attached to an atomic force microscope (AFM) tip was functionalized with cargo via a disulfide-based linker. Chemically tunable mucin chimeras assembled on living cells. In the first step of the pathway, APS reductase catalyzes the reduction of adenosine 5'-phosphosulfate (APS) to adenosine 5'-phosphate (AMP) and sulfite with reducing equivalents from the protein cofactor, thioredoxin. ADAP detects zepto- to attomoles of antibodies in 2 L of sample with a dynamic range spanning 5-6 orders of magnitude. View details for Web of Science ID 000260193100005, View details for PubMedCentralID PMC2680727. Although hundreds of proteins are known to be modified by O-GlcNAc, a strict amino acid consensus sequence for OGT has not been identified. In the mouse genome we have found a homologous ORF that predicts a novel murine GlcNAc 6-O-sulfotransferase with 88% identity to the human enzyme. The critical reagent, a substituted cyclooctyne, possesses ring strain and electron-withdrawing fluorine substituents that together promote the [3 + 2] dipolar cycloaddition with azides installed metabolically into biomolecules. Using a mass spectrometric approach to simultaneously monitor hundreds of lipids, we discovered that the size and abundance of two lipid virulence factors, phthiocerol dimycocerosate (PDIM) and sulfolipid-1 (SL-1), are controlled by the availability of a common precursor, methyl malonyl CoA (MMCoA). The Staudinger ligation is highly selective and reliably forms its product in environs as demanding as live mice. View details for Web of Science ID 000281066400069, View details for PubMedCentralID PMC2923465. Bone biogenesis is thought to occur by templated mineralization of hard apatite crystals by an elastic protein scaffold, a process we sought to emulate with synthetic biomimetic hydrogel polymers. Indeed, we showed previously that the acylation of two mitochondrial proteins at their active site cysteine residues result in their inhibition. We identify and characterize C18ORF8/RMC1 as a regulator of ADC toxicity through its role in endosomal maturation. View details for DOI 10.1016/j.ceb.2004.06.007, View details for Web of Science ID 000223130800003. The recently described O-glycoprotease OpeRATOR presents exciting opportunities for O-glycoproteomics. View details for Web of Science ID 000296312200014. 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. Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. Herein, we sought to identify other palmitoylated proteins in mitochondria using a nonradioactive bio-orthogonal azido-palmitate analog that can be selectively derivatized with various tagged triarylphosphines. Finally the lack of an endogenous human orthologue of cysH and its possible role in defence against adaptive immunity renders CysH an attractive enzyme for further studies as a target for therapeutics active against CTBI. Cyclodextrin complexation is therefore a promising approach for stabilizing compounds that possess the high intrinsic reactivities desired for Cu-free click chemistry. Complete assignment of all (1)H and (13)C resonances in the spectra of these deoxytrehaloses was achieved through the extensive use of 2D [(1)H,(1)H] and [(1)H,(13)C] correlation NMR experiments. Secretory products can both diffuse, although very slowly, through the meshwork pores and interact noncovalently with the matrix. Swarts, B. M., Holsclaw, C. M., Jewett, J. C., Alber, M., Fox, D. M., Siegrist, M. S., Leary, J. In this work, we tested a panel of glycopolymers bearing a variety of lipids to identify those that persist on cell membranes. Hsiao, S. C., Shum, B. J., Onoe, H., Douglas, E. S., Gartner, Z. J., Mathies, R. A., Bertozzi, C. R., Francis, M. B. Elastomeric high-mineral content hydrogel-hydroxyapatite composites for orthopedic applications. We demonstrate, in vitro, that each enzyme in the hexosamine salvage pathway, and the enzymes that affect this dynamic modification (UDP-GlcNAc:polypeptidtyltransferase and O-GlcNAcase), tolerate analogues of their natural substrates in which the N-acyl side chain has been modified to bear a bio-orthogonal azide moiety. Conversely, ETD-based methods, especially EThcD, are indispensable for site-specific analyses of O-glycopeptides. This heterogeneity precludes enrichment strategies that can be universally beneficial for all glycan classes. Dai, T. n., Xie, J. n., Zhu, Q. n., Kamariza, M. n., Jiang, K. n., Bertozzi, C. R., Rao, J. n. Optimal Dissociation Methods Differ for N- and O-glycopeptides. Key advantages of DNA-directed cell binding include the ability to immobilize both adherent and non-adherent cells, to capture cells selectively from a mixed population, to tune the binding properties of the cells, and to reuse substrates prepared with widely available DNA printing technologies. [35], In 2001, Bertozzi and Steve Rosen co-founded Thios Pharmaceuticals in Emeryville, California, the first company to target sulfation pathways. In the present study, we expressed Rv2131c heterologously and found that the protein dephosphorylates PAP in a magnesium-dependent manner, with optimal activity observed between pH 8.5 and pH 9.5 using 0.5 mM MgCl 2. Kaushik, S., Barnes, J., Bainer, R. O., Sa, J. K., Woods, E. C., Kai, F., Przybyla, L., Lakins, J. N., Phillips, J. J., Nam, D., Bertozzi, C. R., Weaver, V. M. Is the Nobel Prize in Chemistry Having a Boston Red Sox Moment? A. Inverting family GH156 sialidases define an unusual catalytic motif for glycosidase action. Pluvinage, J. V., Haney, M. S., Smith, B. H., 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. The mucin-selective protease StcE enables molecular and functional analysis of human cancer-associated mucins. Fernandez-Suarez, M., Baruah, H., Martinez-Hernandez, L., Xie, K. T., Baskin, J. M., Bertozzi, C. R., Ting, A. Y. Molecular orientation of membrane-anchored mucin glycoprotein mimics. A., Bertozzi, C. R. Piperidine-based glycodendrons as protein N-glycan prosthetics. Agarwal, P., van der Weijden, J., Sletten, E. M., Rabuka, D., Bertozzi, C. R. Real-Time Noninvasive Imaging of Fatty Acid Uptake in Vivo. The ketone group on the cell surface can then be covalently ligated under physiological conditions with molecules carrying a complementary reactive functional group such as the hydrazide. Asparagine-linked glycosylation is a common post-translational modification of proteins; in addition to participating in key macromolecular interactions, N-glycans contribute to protein folding, trafficking, and stability. Through this approach, we achieved glycopolypeptides with high molecular weights and low dispersities. 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 10.1021/acschembio.7b00232, View details for PubMedCentralID PMC5850955. Using a green fluorescent protein-mucin fusion protein (SHGFP-MUC5AC/CK) as a FRAP (fluorescence recovery after photobleaching) probe, we have assessed in living mucous cells the relative importance of different protein post-translational modifications on the intragranular organization. View details for Web of Science ID 000177054900001, View details for Web of Science ID 000175790100030, Here we report a concise stereoselective synthesis of myo-inositol via ring-closing metathesis. A convergent synthesis of trehalose. Within this bilayered structure, registry between lattices in two layers was disclosed, whereas the intrinsic symmetry in each layer was altered. 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). Our approach capitalizes on two features shared by these enzymes: their requirement of Golgi localization for activity on cellular substrates and the modularity of their catalytic and localization domains. While this method is highly effective for cultured mammalian cells, we report here a significant improvement of this technique that allows the direct modification of cell surfaces with NHS-DNA conjugates. Preliminary screening has identified compounds that inhibit estrogen sulfotransferase (EST), an enzyme relevant to breast cancer. Bioaerosol volume collection was estimated at 2.3nL (IQR: 1.1-3.6) for RASC-2 compared with 0.08nL (IQR: 0.05-0.10) for RASC-1 (p<0.0001). Carrico, I. S., Carlson, B. L., Bertozzi, C. R. A cell nanoinjector based on carbon nanotubes. Mycobacterium tuberculosis produces numerous exotic lipids that have been implicated as virulence determinants. After completing postdoctoral work at UCSF in the field of cellular immunology, she joined the UC Berkeley faculty in 1996. Thus, despite its inherent advantages in sample collection, OF is not widely used for population screening. WebBio BIO Professor Carolyn Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface sugars important to human health and disease. Mass spectrometry revealed that the N610 residue is part of a consensus N-linked glycosylation motif in the receptor, usually linked to complex glycans. Highlights of recent progress include an extension of the list of instances of selectin participation in inflammatory diseases, further definition of selectin carbohydrate specificities, and identification of their carbohydrate-based ligands. The biosynthesis of these glycoproteins is initiated by a family of polypeptide N-acetyl-alpha-galactosaminyltransferases (ppGalNAcTs) that modify proteins in the secretory pathway. Professor Carolyn Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface sugars important to human health and disease. Phagocytosis is initiated by lateral clustering of receptors, which in turn activates Src-family kinases (SFKs). Individual GalNAc-Ts were rationally engineered to contain an enlarged active site (hole) and probed with a newly synthesized collection of 20 (bumped) uridine diphosphate N-acetylgalactosamine (UDP-GalNAc) analogs to identify enzyme-substrate pairs that retain peptide specificities but are otherwise completely orthogonal to native enzyme-substrate pairs. Methods for the controlled derivatization of glycoproteins are presently limited by the repertoire of natural amino acid side chain and carbohydrate functionalities. Furthermore, we determined that the PAT biosynthetic machinery has no cross-talk with that for sulfolipid-1 despite their related structures. WebBertozzi is trying to drag sugars into the light. Kramer, J., Zhou, M., Delaveris, C., Bertozzi, C. Antibody-enzyme conjugates for targeted glycocalyx editing, Synthesis of solvatochromic probes to label the mycobacterial cell wall and their use in studies of host-pathogen interactions. The glycan symbol nomenclature proposed by Harvey et al. 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. The response of the macrophage proteome to M. tuberculosis lipids reflects the cell's innate defense mechanisms as well as lipid-induced processes that may benefit the pathogen. Bertozzi holds the Anne T. and Robert M. Bass Professorship in the School of Humanities and Sciences at Stanford University. Here, we report that metabolic cross-talk between the N-acetylgalactosamine salvage and O-GlcNAcylation pathways can be exploited for the tagging and identification of O-GlcNAcylated proteins. However, we were able to trap DIFBO by forming a stable inclusion complex with beta-cyclodextrin in aqueous media. 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). Previously, we described the biochemical activity of the sulfotransferase Stf0 that initiates SL-1 biosynthesis. Wang, S., Gray, M. A., Xuan, S., Lin, Y., Byrnes, J., Nguyen, A. I., Todorova, N., Stevens, M. M., Bertozzi, C. R., Zuckermann, R. N., Gang, O. DNA-PKcs has KU-dependent function in rRNA processing and haematopoiesis. Mucin-type O-linked glycosylation is a fundamental post-translational modification that is involved in a variety of important biological processes. Using high-performance liquid chromatography, we quantified the degree of accumulation and reversibility upon acidic compartment neutralization in macrophages and observed that accumulation was greater in infected than in uninfected macrophages. Bertozzi shared the 2022 Nobel Prize in Chemistry with two other scientists: Professor Morten Meldal and Professor K Barry Sharpless. Taken together, this method offers a potentially powerful new chemical tool for studying simultaneous oxidative stress and inflammation processes in living animals during injury, aging, and disease, as well as a versatile approach for concurrent monitoring of multiple analytes using luciferin-based bioluminescence imaging technologies. 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