Factors including glycan heterogeneity, low abundance, and low occupancy can complicate site mapping. The conjugation proceeds under mild conditions with excellent ligation efficiencies and in a stereoselective manner, providing glycopolymers with pendant glycans accommodated mostly in their cyclic beta-glycosidic form. Their involvement in inflammatory disease makes the selectins attractive targets for anti-inflammatory therapy. Armstrong, J. I., Verdugo, D. E., Bertozzi, C. R. Hydrogel polymers from alkylthio acrylates for biomedical applications. Enlightened by our proteomic data, we performed further experiments to show that only the LAM from M. tuberculosis inhibits accumulation of autophagic vacuoles in the macrophage, suggesting a new function for this virulence-associated lipid. We found that the fucose salvage pathway enzymes are expressed during zebrafish embryogenesis but that they process the azide-modified substrates inefficiently. Surprisingly, for three of the enzymes, significant activity was observed with sialylated LacNAc, and two of the enzymes were capable of detectable sulfation of GlcNAc in the context of sialyl Lewis x. Synthetically lipidated recombinant green fluorescent protein (GFP) was shown to be stably anchored to the membrane, and its lateral fluidity was quantitatively characterized by direct fluorescence imaging in supported membranes. This imaging approach should further our understanding of basic metabolic processes and pathological alterations in multiple disease models. Here we show that the cytosolic enzyme N-glycanase 1 (NGLY1, the human PNGase) is essential for Nrf1 activation in response to proteasome inhibition. However, only some of these mutants were able to generate protection equivalent to that of BCG in mice. Studies showed that a bulky glycocalyx potentiates integrin mechanosignalling and tissue tension and promotes a mesenchymal, stem-like phenotype in GBMs. Using rational prediction analysis to recognize putative internal myristoylation sites in caspase-cleaved proteins combined with our nonradioactive chemical detection method, we identify 5 new post-translationally myristoylatable proteins (PKC epsilon, CD-IC2, Bap31, MST3, and the catalytic subunit of glutamate cysteine ligase). Progeny thereof may be powerful tools for controlling O-linked glycosylation in cells. Secretory products can both diffuse, although very slowly, through the meshwork pores and interact noncovalently with the matrix. The most potent examined, 1-68A, is a pH-dependent, two-step, covalent inhibitor of Escherichia coli LpxC that competes with UDP to bind the enzyme in the first step of inhibition. [89][90][91], Bertozzi is a lesbian and has been out since the late 1980s. We observed crosslinking between FG-repeat nucleoporins and nuclear transport factors, suggesting that O-GlcNAc residues are intimately associated with essential recognition events in nuclear transport. We disabled key enzymes required for each of the three pathways in M. smegmatis by allelic replacement. CD22 mediates the anti-phagocytic effect of alpha2,6-linked sialic acid, and inhibition of CD22 promotes the clearance of myelin debris, amyloid-beta oligomers and alpha-synuclein fibrils in vivo. Carolyn Bertozzi, PhD, was one of three scientists to be awarded the 2022 Nobel Prize in Chemistry earlier today for the development of click chemistry and bio-orthogonal chemistry. Van de Bittner, G. C., Bertozzi, C. R., Chang, C. J. To obtain structural information about these biomolecules, and the modifications they may undergo during different stages of cell growth and development, a mass spectrometry-based method was developed and used to obtain unambiguous structural information on the glycosaminoglycans (GAGs) that comprise heparin/HS. 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. We used this strategy to construct a paracrine signaling network in isolated 3-dimensional microtissues. In vivo, BPA appears to have greater activity than is suggested by its estrogen receptor (ER) binding affinity. However, N-butanoylmannosamine and N-pentanoylmannosamine are effective inhibitors of polysialic acid (PSA) synthesis in stably transfected HeLa cells expressing NCAM and the polysialyltransferase STX. This enzyme is also the first characterized ppGalNAc-T of protozoan origin. The versatility of this technology was demonstrated by an example of selective drug delivery. Cells were decorated with biotin through selective conjugation to ketone groups, and selectively killed in the presence of a ricin A chain-avidin conjugate. Mycobacterial infection leads to the formation of characteristic immune aggregates called granulomas, a process accompanied by dramatic remodeling of the host vasculature. We identified and characterized a conserved mycobacterial sulfotransferase, Stf0, which generates the T2S moiety of SL-1. She grew up in Lexington, Massachusetts with two sisters, one of which is on the mathematics faculty at the University of California, Los Angeles (UCLA). bertozzi@stanford.edu. The data suggest that the ppGalNAcTs can be classified into at least four types, which working together, are able to produce densely glycosylated mucin glycoproteins. There is growing interest in extending this progress to O-glycoproteomics, which necessitates comparisons of method performance for the two classes of glycopeptides. This template-driven mineralization technique provides an efficient approach toward bonelike composites with high mineral-hydrogel interfacial adhesion strength. Diptericin increased the permeability of the outer and inner membranes of Escherichia coli D22 cells, suggesting possible mechanisms of action. It deftly subverts the bactericidal mechanisms of alveolar macrophages, ultimately inducing granuloma formation and establishing long-term residence in the host. Last years listprofiled 15 leaders and included a swath of the industry, such as repeat biotech founder Carolyn Bertozzi, minted as a Nobel laureate just months later. 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). However, the diversity found in glycoproteins has undermined efforts to describe the intact glycoproteome via mass spectrometry (MS). In conjunction with techniques for site-specific introduction of aldehydes into proteins, the Pictet-Spengler ligation offers a means to generate stable bioconjugates for medical and materials applications. View details for DOI 10.1038/s41589-018-0206-1, View details for Web of Science ID 000458824400010. Detection of metabolites and post-translational modifications can be achieved using the azide as a bioorthogonal chemical reporter. Still, glycoconjugate synthesis requires the manipulation of multiple stereocenters and protecting groups and remains the domain of a few expert laboratories around the world. Hsiao, S. C., Crow, A. K., Lam, W. A., Bertozzi, C. R., Fletcher, D. A., Francis, M. B. Rabuka, D., Forstner, M. B., Groves, J. T., Bertozzi, C. R. In vivo imaging of membrane-associated glycans in developing zebrafish. Molecular imaging with chemical reporters offers a new avenue for probing changes in the glycome that accompany development and disease. However, a detailed structural analysis of S881 has remained elusive. Collectively, these results indicate that the distortion/interaction model combined with bond angle analysis will enable predictions of cyclooctyne reactivity and the rational design of new reagents for copper-free click chemistry. In doing so, we examine prevailing notions about the number of modifications displayed on human proteins and how they combine to generate the protein diversity underlying health and disease. This function deteriorates during ageing and neurodegenerative disease, concomitant with cognitive decline. 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. Proteobacterial ATPS overcomes this energetically unfavorable reaction by associating with a regulatory G protein, coupling the energy of GTP hydrolysis to APS formation. 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. The rapid assembly of "core 1"and "core 3" O-linked glycopeptide mimetics was accomplished in this fashion. View details for DOI 10.1016/j.bmcl.2011.05.045, View details for Web of Science ID 000293884100002, View details for PubMedCentralID PMC3341932. Regrettably, conventional biochemical and genetic methods often fall short for the study of glycans, because their structures are often not precisely defined at the genetic level. 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. [4] Bertozzi is also an Investigator at the Howard Hughes Medical Institute (HHMI)[5] and is the former Director of the Molecular Foundry, a nanoscience research center at Lawrence Berkeley National Laboratory. In contrast, exogenous (13)C-labeled N-acetylneuraminic acid ([(13)C]NeuAc) and N-glycolylneuraminic acid (NeuGc) were efficiently incorporated into LOS in a dose-dependent fashion. Mockl, L., Pedram, K., Roy, A., Krishnan, V., Gustavsson, A., Dorigo, O., Bertozzi, C., Moerner, W. Enzyme toolkit for selective enrichment and analysis of mucin-domain glycoproteins. [16], Bertozzi completed her Ph.D. in chemistry at University of California, Berkeley in 1993 with Mark Bednarski, working on the chemical synthesis of oligosaccharide analogs. Cell surface glycosylation is thought to be involved in barrier function against microbes at mucosal surfaces. Glioblastoma multiforme (GBMs) are recurrent lethal brain tumours. View details for Web of Science ID 000304492700020. Several changes have been made to the SNFG page in the past year to update the rules for depicting glycans using the SNFG, to include more examples of use, particularly for non-mammalian organisms, and to provide guidelines for the depiction of ambiguous glycan structures. A fluorogenic screening platform enables directed evolution of an alkyne biosynthetic tool. Fluorogenic probes activated by bioorthogonal chemical reactions can enable biomolecule imaging in situations where it is not possible to wash away unbound probe. Phosphorylation of Rv0516c regulated the abundance of EspA, a virulence-associated substrate of the type VII ESX-1 secretion system. The apparent rate constants for the hydrolysis and disappearance of the cell surface conjugates were determined, as well as the apparent rate constant for the formation of covalent bonds with cell surface ketones. The approach was validated by labeling a recombinant glycoprotein that is known to possess O-linked glycans with GalNAz. Here, we engineer living cells to tag glycans with editable chemical functionalities while providing information on biosynthesis, physiological context, and glycan fine structure. 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. Comparison of these data to images of wild-type SbpA layers on intact cells gave insight into the interactions responsible for bilayer formation. Bertozzi, C. R., Fukuda, S., ROSEN, S. D. CRACKING THE CARBOHYDRATE CODE FOR SELECTIN RECOGNITION, IDENTIFICATION OF THE SULFATED MONOSACCHARIDES OF GLYCAM-1, AN ENDOTHELIAL-DERIVED LIGAND FOR L-SELECTIN. Our work provides a blueprint for a wide variety of future chemical approaches to identify, visualize, and characterize dynamic O-GlcNAc signaling. Treatment of MCF-7 cells with BPAS leads to desulfation and uptake of BPA. 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. These modified GFPs were incorporated in supported lipid bilayers, and their mobilities were analyzed using fluorescence correlation spectroscopy. Carolyn Bertozzi is a chemist who has made important contributions to understanding how cells interact. We propose a model in which Golgi enzyme localization and competition orchestrate the biosynthesis of L-selectin ligands. Kumar, P., Schelle, M. W., Jain, M., Lin, F. L., Petzold, C. J., Leavell, M. D., Leary, J. Proof of principle was performed by using various heparin/HS samples isolated from bovine and porcine tissues. View details for DOI 10.1021/acsinfecdis.6b00106, View details for Web of Science ID 000388161300007. Such labeled proteins can then be treated with azide-functionalized probes to ligate affinity handles or fluorophores to the PKMT substrates. Lin, F. L., Hoyt, H. M., van Halbeek, H., Bergman, R. G., Bertozzi, C. R. Synthetic glycopeptides and glycoproteins as tools for biology, Functional hydrogel-biomineral composites inspired by natural bone, Azido sialic acids can modulate cell-surface interactions, A small-molecule switch for Golgi sulfotransferases. View details for DOI 10.1038/s41467-019-12684-7. These results should facilitate mechanistic studies and the development of small molecule inhibitors of this enzyme family to ameliorate chronic inflammatory diseases. She has been awarded the Lemelson-MIT Prize, the Heinrich Wieland Prize, and a MacArthur Foundation Fellowship, among many others. O-Glycosylation affects relatively minor components of cell surfaces. We observed dramatic nanoscopic morphological transformations accompanying charge-induced chromatic transitions, suggesting that both side-chain disordering and main-chain rearrangement play important roles in altering the effective conjugation lengths of the poly(ene-yne). Tomlin, F. M., Gordon, C. G., Han, Y., Wu, T. S., Sletten, E. M., Bertozzi, C. R. Targeting glyco-immune checkpoints for cancer immune therapy, F Rapid detection of Mycobacterium tuberculosis in sputum with a solvatochromic trehalose probe. Sulfite is then released in a thioredoxin-dependent manner. Carroll, K. S., Gao, H., Chen, H. Y., Leary, J. Here we report the facile synthesis of a difluorobenzocyclooctyne (DIFBO) that combines these modifications. Noncovalent complexes of the holoprotein with several ligands, including APS, thioredoxin, and AMP, were also investigated. Finally, the structure of an intermediate that accumulates under anhydrous conditions was identified. Each enzyme preferred a terminal GlcNAc residue, and was impeded by the addition of a beta1,4-linked Gal residue (i.e., terminal LacNAc). On this Wikipedia the language links are at the top of the page across from the article title. View details for Web of Science ID 000355248100027, View details for DOI 10.1021/acscentsci.5b00185, View details for PubMedCentralID PMC4827500. Driessen, M. D., Going, C. C., Woo, C. M., Pitteri, S. J., Bertozzi, C. R. New therapeutic avenues for NGLY1 deficiency, A TENSION-MEDIATED GLYCOCALYX FEEDBACK LOOP PROMOTES A MESENCHYMAL, STEM-LIKE PHENOTYPE IN GLIOBLASTOMA. WebProfessor 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. We have coexpressed a human GST-5 cDNA with a GlyCAM-1/IgG fusion protein in COS-7 cells and observed four-fold enhanced [(35)S]sulfate incorporation into this mucin acceptor. 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 Cu(I)-catalyzed reaction was found to be most efficient for detecting azides in protein samples but was not compatible with live cells due to the toxicity of the reagents. Genes involved in cell signaling, extracellular matrix remodeling, inflammation, angiogenesis and hypoxia were all activated in cells on the collagen-GAG mesh. Laughlin, S. T., Baskin, J. M., Amacher, S. L., Bertozzi, C. R. Rapid detection, discovery, and identification of post-translationally myristoylated proteins during apoptosis using a bio-orthogonal azidomyristate analog. View details for DOI 10.1021/acscentsci.6b00070, View details for PubMedCentralID PMC4827488. Dinkele, R., Gessner, S., McKerry, A., Leonard, B., Seldon, R., Koch, A. S., Morrow, C., Gqada, M., Kamariza, M., Bertozzi, C. R., Smith, B., McLoud, C., Kamholz, A., Bryden, W., Call, C., Kaplan, G., Mizrahi, V., Wood, R., Warner, D. F. Modulation of immune cell reactivity with cis-binding Siglec agonists. We describe a metabolism-based approach to the selection of mutants in glycoconjugate biosynthesis that provides insight into regulatory mechanisms for oligosaccharide expression and metabolic flux. This assay is 1,000-10,000 times more analytically sensitive than clinical enzyme-linked immunoassays (EIAs), displaying both 100% clinical sensitivity and 100% specificity for detecting HIV antibodies within OF samples. Some of these techniques remove obstacles to glycoprotein synthesis by installing nonnative linkages and other modifications for facilitated assembly. Woo, C. M., Felix, A., Byrd, W. E., Zuegel, D. K., Ishihara, M., Azadi, P., Iavarone, A. T., Pitteri, S. J., Bertozzi, C. R. Click-Chemistry Based High Throughput Screening Platform for Modulators of Ras Palmitoylation. An N-azidoacetylmannosamine derivative caged with a peptide substrate for the prostate-specific antigen (PSA) protease was converted to cell-surface azido sialic acids in a PSA-dependent manner. Comparison of the cDNA and genomic DNA sequences reveals that this transferase is encoded by 10 exons in a 10 kb region. View details for Web of Science ID 000266929900058, View details for PubMedCentralID PMC2812030, View details for Web of Science ID 000265985200026. Subsequently, the worms were reacted via copper-free click reaction with fluorophore-conjugated difluorinated cyclooctyne (DIFO) reagents. Dibenzoselenacycloheptynes were prepared in three steps from commercially available reagents and trapped in situ with benzyl azide to form the corresponding triazoles. NodST catalyzes the sulfuryl group transfer from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to chitobiose, generating 3'-phosphoadenosine 5'-phosphate (PAP) and chitobiose-6-OSO(3)(-) as products. 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. In IsoTaG, metabolic labeling of the glycoproteome is combined with (i) chemical enrichment and isotopic recoding of glycopeptides to select peptides for targeted glycoproteomics using directed MS and (ii) mass-independent assignment of intact glycopeptides. Consequently, the sulfate assimilation pathway of M. tuberculosis proceeds from sulfate through APS, which is acted on by APS reductase in the first committed step toward cysteine and methionine. Monomeric sialyl Lewis(X) (sLe(x)) and sLe(x)-like oligosaccharides are minimal structures capable of supporting selectin binding in vitro. The reaction features a large dynamic range of reactivity, showcasing second-order rate constants as high as 2.310(3) M(-1) s(-1) using diboron reaction partners. Wan, S. J., Sullivan, A. Research into protein glycosylation, therefore, has benefited from homogeneous, structurally-defined glycoproteins obtained by chemical synthesis. Baker Family Director, Sarafan ChEM-H. Anne T. and Robert M. Bass Professor of Chemistry. Azides installed within cell surface glycoconjugates by metabolism of a synthetic azidosugar were reacted with a biotinylated triarylphosphine to produce stable cell-surface adducts. A., Ge, Y. n., Gunawardena, J. n., Hendrickson, R. C., Hergenrother, P. J., Huber, C. G., Ivanov, A. R., Jensen, O. N., Jewett, M. C., Kelleher, N. L., Kiessling, L. L., Krogan, N. J., Larsen, M. R., Loo, J. A FRET-based fluorogenic phosphine for live-cell Imaging with the Staudinger ligation, DNA-Coated AFM Cantilevers for the Investigation of Cell Adhesion and the Patterning of Live Cells. No BPAS is found inside the cells. The reaction provided a means to label the glycoconjugate-bound azidosugars with biochemical probes. Further, we propose that the method reported here could find widespread use in investigating the functional consequences of O-GlcNAcylation. A., Johnson, A. G., George, B. M., Majzoub, K., Villalta, P. W., Carette, J. E., Bertozzi, C. R. Synthetic Siglec-9 Agonists Inhibit Neutrophil Activation Associated with COVID-19, Delaveris, C. S., Wilk, A. J., Riley, N. M., Stark, J. C., Yang, S. S., Rogers, A. J., Ranganath, T., Nadeau, K. C., Blish, C. A., Bertozzi, C. R., Stanford COVID-19 Biobank. They originate from biosynthetic pathways comprising an assembly line of glycosyltransferases within the Golgi compartment. In this paper, we describe the design, synthesis, and biological application of a new phosphine probe for real-time imaging of cell-surface glycans using bioluminescence. Mycobacterium tuberculosis possesses an unusual cell wall that is replete with virulence-enhancing lipids. 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. [9] View details for DOI 10.1073/pnas.0601167103, View details for Web of Science ID 000239069400007, View details for PubMedCentralID PMC1502431. Thus, cell surface ketones are a potential vehicle for a metabolically controlled small-molecule drug delivery system. The electronic and steric properties of the ester had no significant impact on the overall rate but did affect product ratios. 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. Finally, we engineered the Golgi-resident glycosyltransferase FucT7 for tunable control by Tmp-SLF in mammalian cells. The building block was incorporated into a synthetic peptide derived from the active site of a Mycobacterium tuberculosis sulfatase. Our data show that over 50% of O-glycopeptides in our sample generated from combined digestion using OpeRATOR and trypsin contain multiple O-glycosites, indicating that collision-based fragmentation alone is not sufficient. IsoTaG is therefore an effective platform for identification of intact glycopeptides labeled by alkynyl or azido sugars and will facilitate further studies of the glycoproteome. A., Bertozzi, C. R., Stout, C. D. A chemical reporter strategy to probe glycoprotein fucosylation. A., Quang, C. N., Bertozzi, C. R. A sulfated metabolite produced by stf3 negatively regulates the virulence of Mycobacterium tuberculosis. The sulfation of trehalose is required for the biosynthesis of sulfolipid-1, the most abundant sulfated metabolite found in Mycobacterium tuberculosis. A., Sletten, E. M., Bertozzi, C. R., Popik, V. V., Ting, A. Y. Low molecular weight and singly charged fragments, obtained by a combination of gel filtration and anion-exchange chromatography, were analyzed. View details for PubMedCentralID PMC5924460. Studies of 4Fe-4S cluster stability and cysteine reactivity in the presence and absence of substrates, and in the free enzyme versus the covalent enzyme-intermediate (E-Cys-S-SO(3)(-)), suggest a structural rearrangement that occurs during the catalytic cycle. Here we use combinatorial target-guided ligand assembly to discover the first known inhibitors of human TPST-2. Advances in cellular imaging and in small molecule-controlled gene expression, signal transduction and cell surface modification are discussed in this review. Mougous, J. D., Senaratne, R. H., Petzold, C. J., Jain, M., Lee, D. H., Schelle, M. W., Leavell, M. D., Cox, J. S., Leary, J. Here we use high-resolution, high-mass-accuracy, and tandem mass spectrometry to characterize the structure of S881. Proteomics analyses were also performed and confirmed enrichment of plasma membrane proteins with some contamination from endoplasmic reticulum and other membranes. To understand the adaptation of Mycobacterium tuberculosis to the intracellular environment, we used comprehensive metabolite profiling to identify the biochemical pathways utilized during growth on cholesterol, a critical carbon source during chronic infection. Kinetic analysis of the mutants identified residues that are essential for catalytic activity. As sulfated molecules are common mediators of cell-cell interactions, the sulfotransferases and sulfatases may be involved in regulating host-pathogen interactions. These collective results provide a detailed mechanistic framework for understanding why nature chose this structurally unique monocopper active site to catalyze oxidase chemistry for sulfatase activation. Vertebrate glycans constitute a large, important, and dynamic set of post-translational modifications that are notoriously difficult to manipulate and image. View details for Web of Science ID 000169081700029. Here we describe the characterization and application of a synthetic riboswitch-based system, which comprises a mycobacterial promoter for transcriptional control and a riboswitch for translational control. The assay is suitable for high-throughout screening of compounds and may find use in the identification of selectin antagonists with anti-inflammatory potential. 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. Bifunctional, fluorinated cyclooctynes were used for the in situ "click" crosslinking of azide-terminated photodegradable star polymers, yielding photodegradable polymeric model networks with well-defined structures and tunable gelation times. View details for DOI 10.1128/AAC.01639-16, View details for PubMedCentralID PMC5328571. Interactions of mucin glycoproteins with cognate receptors are dictated by the structures and spatial organization of glycans that decorate the mucin polypeptide backbone. In 1961, Wittig and Krebs noted that the strained, cyclic alkyne cyclooctyne reacts violently when combined neat with phenyl azide, forming a triazole product by 1,3-dipolar cycloaddition.
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