Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. View details for Web of Science ID 000180258800025, View details for Web of Science ID 000181755600011, View details for Web of Science ID 000185102400018. In this study, we employed two state-of-the-art quantitative proteomic approaches, metabolic labeling SILAC and chemical isobaric tagging iTRAQ, to study changes in macrophage protein expression in response to exposure to M. tuberculosis lipids. Selective chemical reactions enacted within a cellular environment can be powerful tools for elucidating biological processes or engineering novel interactions. A., Bertozzi, C. R. Investigation of the iron-sulfur cluster in Mycobacterium tuberculosis APS reductase: Implications for substrate binding and catalysis. A combination of quantitative microscopy, mutational analysis, and interaction studies indicate that SteA and SteB form a complex that localizes to the cytokinetic ring to promote cell separation by RipC-FtsEX and may coordinate its PG remodeling activity with the biogenesis of other envelope layers during cell division. Such structural alterations to cell surface glycans can be used to probe carbohydrate-dependent phenomena. Sialic Acid Glycobiology Unveils Trypanosoma cruzi Trypomastigote Membrane Physiology. summa cum laude in chemistry from Harvard University, where she worked with Professor Joe Grabowski on the design and construction of a photoacoustic calorimeter. Bowman, K. G., Cook, B. N., de Graffenried, C. L., Bertozzi, C. R. The evolving academic research environment, Chemical synthesis of lymphotactin: A glycosylated chemokine with a C-terminal mucin-like domain. Maturation is driven by the phosphoinositide kinase PIKfyve. Indeed, O-glycopeptides modified exclusively at the N-terminus would enable O-glycoproteomic methods to rely solely on collision-based fragmentation rather than electron-driven dissociation because glycan-retaining peptide fragments would not be required for localization. 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. 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. The system was used to induce and repress heterologous protein overexpression reversibly, to create a conditional gene knockdown, and to control gene expression in a macrophage infection model. The ligand used is a mucin-like glycoprotein known as GlyCAM-1, which is derived from high endothelial venules in secondary lymphoid organs. The synthetic, full-length polypeptide proved to be active in growth inhibition assays with an IC(50) of approximately 250 nM, a concentration similar to that found in the insect hemolymph. Mucin glycoproteins contribute to a wide range of cell-surface phenomena. We report the synthesis of an alpha-formylglycine building block suitable for Fmoc-based solid-phase peptide synthesis. The biophysical properties of the system are characterized, and the technique is used to form complex cellular patterns with single-cell line widths and self-assembled cellular microarrays. Our glycan-specific assay can be paired with traditional proximity ligation assays to simultaneously determine the change in total protein levels. Here we report a method for rapid profiling of fucosylated glycoproteins from human cells using 6-azido fucose as a metabolic label. Mougous, J. D., Petzold, C. J., Senaratne, R. H., Lee, D. H., Akey, D. L., Lin, F. L., Munchel, S. E., Pratt, M. R., Riley, L. W., Leary, J. Mutants with defects in sulfate assimilation indicate that the fate of sulfur in M. tb is a critical survival determinant for the bacteria during infection and suggest novel targets for tuberculosis drug therapy. 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. We synthesized a 1338 member library of uridine analogs directed to the epimerase by virtue of substrate mimicry. Furthermore, we demonstrate that the metabolic diversity of nature enables the use of naturally occurring functional groups that display inherent biocompatibility alongside abiotic components for organism-specific applications. The cysH mutant was also susceptible to peroxynitrite and hydrogen peroxide in vitro. Importantly, we detected increased PDIM synthesis in bacteria growing within host tissues and in bacteria grown in culture on odd-chain fatty acids. These observations suggest crosstalk between autophagy and phagocytosis that may be relevant to the innate immune response of macrophages. Her father, William Bertozzi, was a physics professor at MIT. View details for DOI 10.1002/pmic.200900708, View details for Web of Science ID 000273515000001, View details for PubMedCentralID PMC2882983. 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. StcEE447D is a pan-mucin stain derived from enterohemorrhagic Escherichia coli that is tolerant to a wide range of glycoforms. Bertozzi subsequently optimized the bioorthogonal reaction using an azide as a binding partner for the fluorescent tag. 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. 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. We applied the technique to site-specific modification of monoclonal antibodies, the fastest growing class of biopharmaceuticals, as well as membrane-associated and cytosolic proteins expressed in mammalian cells. View details for Web of Science ID 000435537701267. We tested this prediction by investigating whether bulky glycoproteins in the glycocalyx promote a tumour phenotype in human cells by increasing integrin adhesion and signalling. Positioned at the C-terminus of many eukaryotic proteins, the glycosylphosphatidylinositol (GPI) anchor is a posttranslational modification that anchors the modified protein in the outer leaflet of the cell membrane. A., Solomon, E. I., Bertozzi, C. R. Formylglycine-generating enzyme binds substrate directly at a mononuclear Cu(I) center to initiate O2 activation. Dithiothreitol, glutathione and the C207A mutant of E. coli LpxC prevent the formation of a covalent complex by 1-68A, suggesting a role for Cys-207 in inhibition. Tuberculosis (TB) disease is a global epidemic caused by the pathogenic Mycobacterium tuberculosis (Mtb). Lemieux, G. A., de Graffenried, C. L., Bertozzi, C. R. Metabolic incorporation of unnatural sialic acids into Haemophilus ducreyi lipooligosaccharides. Although the mechanisms of Golgi enzyme localisation are still under debate, the distribution of these enzymes among the Golgi cisternae can dictate the overall structures produced by the cell. In all assays, activity appeared glycosylation independent. This strategy uses a two-step labeling procedure in which an unnatural sugar analogue containing a functional handle is (1) incorporated into sugar-bearing proteins via the cell's own biosynthetic machinery and then (2) detected with an exogenously added probe. Grand Challenges in Chemistry for 2016 and Beyond. The new molecule class may be able to degrade some cardiovascular disease and cancer targets. Thus, choice of enrichment strategy has profoundimplications on experimental outcomes. Most bacteria possess only one trehalose biosynthesis pathway and do not elaborate the disaccharide into more complex metabolites, suggesting a distinct role for trehalose in mycobacteria. View details for DOI 10.1073/pnas.0506855103, View details for Web of Science ID 000236472500008, View details for PubMedCentralID PMC1405625. The membrane-associated acyltransferase Chp1 accepts a synthetic diacyl sulfolipid and transfers an acyl group regioselectively from one donor substrate molecule to a second acceptor molecule in two successive reactions to yield a tetraacylated product. 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. The C-type lectins dectin-1 and dectin-2 contribute to innate immunity against microbial pathogens by recognizing their foreign glycan structures. Kohler, J. J., Czlapinski, J. L., Laughlin, S. T., Schelle, M. W., de Graffenried, C. L., Bertozzi, C. R. Metabolic functionalization of recombinant glycoproteins. 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. View details for DOI 10.1016/j.jasms.2006.08.010, View details for Web of Science ID 000244109300001, View details for PubMedCentralID PMC2755055. Portraits of the 2022 Nobel laureates in Chemistry Carolyn R. Bertozzi (L), Morten Meldal (C) and K. Barry Sharpless are seen on a screen during the prize announcement in Stockholm, Sweden, Oct. 5, 2022. filexlib. We seeded collagen-glycosaminoglycan meshes, a widely used tissue engineering scaffold material, with human IMR-90 fibroblasts and compared transcript levels with control cells grown on tissue culture polystyrene. Here we demonstrate that cell surfaces can be engineered to display synthetic bioactive polymers at defined densities by exogenous membrane insertion. 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. Here we report that a bulky glycocalyx promotes the expansion of disseminated tumor cells in vivo by fostering integrin adhesion assembly to permit G1 cell cycle progression. View details for DOI 10.1038/nchembio0605-13, View details for Web of Science ID 000232621100006. Jain, M., Petzold, C. J., Schelle, M. W., Leavell, M. D., Mougous, J. D., Bertozzi, C. R., Leary, J. Mucin biology has been difficult to study at the molecular level, in part, because methods to manipulate and structurally characterize mucin domains are lacking. Here we report the development of an HIV OF assay based on Antibody Detection by Agglutination-PCR (ADAP) technology. Bertozzi received a bachelors degree in chemistry from Harvard University in 1988 and a doctorate in the same subject from the University of California, Berkeley in 1993. Analyses revealed that recurrent GBMs have increased tension and express high levels of glycoproteins that increase the bulkiness of the glycocalyx. Molecules terminated with Texas Red lie flat at the membrane (height, 0 +/- 2 nm), implying that interactions between Texas Red and the bilayer dominate the polymers' free energy. 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. Nrf1 is constitutively translocated into the ER lumen, N-glycosylated, and then targeted for proteasomal degradation via the ER-associated degradation (ERAD) pathway. Hang, H. C., Yu, C., Pratt, M. R., Bertozzi, C. R. Detection of bacteria in suspension by using a superconducting quantum interference device. This system provides a unique framework with which to study the behavior of mucin-like macromolecules in a controlled, cell surface-mimetic environment. A., Shrager, J. The process of generating aldehyde-tagged protein followed by chemical conjugation and purification takes 20 d. View details for DOI 10.1038/nprot.2012.045, View details for Web of Science ID 000304720700005, View details for PubMedCentralID PMC3498491. This protocol details the syntheses of the azido sugars N-azidoacetylmannosamine (ManNAz), N-azidoacetylgalactosamine (GalNAz), N-azidoacetylglucosamine (GlcNAz) and 6-azidofucose (6AzFuc), and the detection reagents phosphine-FLAG and phosphine-FLAG-His6. The nematode Caenorhabditis elegans is an excellent model organism for studies of glycan dynamics, a goal that requires tools for imaging glycans in vivo. She is known for creating the term "bioorthogonal chemistry" for chemical reactions with living systems. The glycan symbol nomenclature proposed by Harvey et al. Muia, R. P., Yu, H., Prescher, J. This assay allows for direct product detection on the membrane, obviating excessive washing and elution steps endemic to other assays. Dr. Bertozzi completed her undergraduate degree in Chemistry at Harvard University and her Ph.D. at UC Berkeley, focusing on the chemical synthesis of oligosaccharide analogs. During postdoctoral work at UC San Francisco, she studied the activity of endothelial oligosaccharides in promoting cell adhesion at sites of inflammation. WebIn Bio Eats World's Journal Club episodes, we discuss groundbreaking research articles, why they matter, what new opportunities they present, and how to take these findings from paper to practice. As with native mucins, the cell-surface display of CholA-anchored glycopolymers influenced the focal adhesion distribution. Shin, Y., Winans, K. A., Backes, B. J., KENT, S. B., Ellman, J. Shieh, P., Siegrist, M. S., Cullen, A. J., Bertozzi, C. R. Glycocalyx engineering reveals a Siglec-based mechanism for NK cell immunoevasion. The compounds did not inhibit other mammalian glycosyltransferases or nucleotide sugar utilizing enzymes, suggesting selectivity for the ppGalNAcTs. Grunwell, J. R., Rath, V. L., Rasmussen, J., Cabrilo, Z., Bertozzi, C. R. Discovery of sulfated metabolites in mycobacteria with a genetic and mass spectrometric approach. Single Jurkat cells exhibited an extracellular acidification rate of 11 milli-pH min(-1), while primary T cells exhibited only 2 milli-pH min(-1). [27], Bertozzi also previously served on the research advisory board of several pharmaceutical companies including GlaxoSmithKline, and until recently Eli Lilly.[48]. Synthetic mimics of the complex assemblies found on cell surfaces can modulate cellular interactions and are under development as therapeutic agents. 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. We report the 2.7 A resolution crystal structure of Pseudomonas aeruginosa APS reductase in the thiosulfonate intermediate form of the catalytic cycle and with substrate bound. Here, we report a system for conditional activation of Golgi-resident sulfotransferases using a chemical inducer of dimerization. Incorporation of sialosides into LOS was assessed by matrix-assisted laser desorption and electrospray ionization mass spectrometry. Her lab focuses on profiling changes in cell surface glycosylation associated with cancer, inflammation and bacterial infection, and exploiting this information for development of diagnostic and therapeutic approaches, most recently in the area of immuno-oncology. Positioned at the C-terminus of many eukaryotic proteins, the glycosylphosphatidylinositol (GPI) anchor is a posttranslational modification that anchors the modified proteins in the outer leaflet of the plasma membrane. T-cell progenitors originate in the bone marrow and are mobilized to the blood at regular intervals by unknown signals. Cell surface lipooligosaccharides (LOS) of H. ducreyi are thought to play important biological roles in host infection. Sialic acid is a component of many tumor-associated oligosaccharide antigens. Yao, J. We also show that the integral membrane protein Sap and MmpL8 are both essential for sulfolipid transport. Using this knowledge, glycosyltransferase assembly lines have been redesigned for the production of specific glycan structures using protein engineering and chemical approaches. A step in this direction will be the development of tools to identify metabolites that share common structural features. 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. View details for DOI 10.1002/anie.201508861, View details for Web of Science ID 000368061800024, View details for PubMedCentralID PMC4715665. Thus, the protein-carbohydrate interactions, as well as other interactions contributing to ligand recognition, can be investigated. She is also an Investigator at the Howard Hughes Medical Institute (HHMI) and is the former Director of the Molecular Foundry. She coined the term "bioorthogonal chemistry" for chemical reactions compatible with living systems. Using a multicolor detection strategy, we performed a spatiotemporal analysis of glycan expression and trafficking and identified patterns that would be undetectable with conventional molecular imaging approaches. We fed cells an unnatural monosaccharide, a modified mannosamine that replaced the acetyl group with a levulinate group (ManLev). Pathogenic bacteria have developed numerous mechanisms to survive inside a hostile host environment. Z. O-Pair Search with MetaMorpheus for O-glycopeptide characterization. The modification modulates protein-protein interactions in the extracellular environment. This suggests that post-translational myristoylation of caspase-cleaved proteins represents a novel mechanism widely used to regulate cell death. View details for Web of Science ID 000259139900020, View details for PubMedCentralID PMC2721638. Ooi, Y. S., Majzoub, K., Flynn, R. A., Mata, M. A., Diep, J., Li, J. K., van Buuren, N., Rumachik, N., Johnson, A. G., Puschnik, A. S., Marceau, C. D., Mlera, L., Grabowski, J. M., Kirkegaard, K., Bloom, M. E., Sarnow, P., Bertozzi, C. R., Carette, J. E. A novel therapeutic modality of inhibiting the glyco-immune checkpoint axis to treat cancer. They also suggest increased P. aeruginosa adhesion to MyD88-/- and blotted corneas is not due to reduction in total surface glycosylation, and for tissue paper blotting is likely due to cell permeabilization.-Jolly, A. L., Agarwal, P., Metruccio, M. M. E., Spiciarich, D. R., Evans, D. J., Bertozzi, C. R., Fleiszig, S. M. J. Corneal surface glycosylation is modulated by IL-1R and Pseudomonas aeruginosa challenge but is insufficient for inhibiting bacterial binding. Beatty, K. E., Fisk, J. D., Smart, B. P., Lu, Y. Y., Szychowski, J., Hangauer, M. J., Baskin, J. M., Bertozzi, C. R., Tirrell, D. A. Bioluminescent Probes of Sulfatase Activity. Bertozzi, C. R., SINGER, M. S., ROSEN, S. D. L-selectin-carbohydrate interactions: Relevant modifications of the Lewis x trisaccharide. 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. 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. View details for DOI 10.1073/pnas.0307128101, View details for Web of Science ID 000187937200026, View details for PubMedCentralID PMC314150, View details for DOI 10.1002/anie.200352673, View details for Web of Science ID 000220266000010, View details for DOI 10.1002/anie.200454235, View details for Web of Science ID 000224592400009, View details for DOI 10.1002/anie.200460620, View details for Web of Science ID 000225445200005, View details for Web of Science ID 000223490500010. Of the sequence motifs that are associated with 4Fe-4S centers, the cysteine dyad is atypical and has generated discussion with respect to coordination as well as the cluster's larger functional significance. View details for Web of Science ID 000222930600016. View details for DOI 10.1038/NCHEMBIO.1388, View details for Web of Science ID 000328854900013. Previously, we reported targeting of the blue fluorophore coumarin to cellular proteins fused to a 13-amino acid recognition sequence (LAP), catalyzed by a mutant of the Escherichia coli enzyme lipoic acid ligase (LplA). View details for DOI 10.1021/acschembio.7b00232, View details for PubMedCentralID PMC5850955. 275, 21075-21080). WebCarolyn Ruth Bertozzi (born October 10, 1966) is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. 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. One mechanism of proteasome inhibitor resistance may involve the transcription factor Nuclear Factor, Erythroid 2 Like 1 (NFE2L1, also referred to as Nrf1), which responds to proteasome insufficiency or pharmacological inhibition by upregulating proteasome subunit gene expression. Glycans are attractive targets for molecular imaging but have been inaccessible because of their incompatibility with genetically encoded reporters. These included proteins involved in the immune response, oxidation and reduction, and vesicle transport, as well as other cellular processes. O-Linked -N-acetylgalactosamine (O-GalNAc) glycans constitute a major part of the human glycome. Dynamic imaging of proteins in live cells is routinely performed by using genetically encoded reporters, an approach that cannot be extended to other classes of biomolecules such as glycans and lipids. View details for DOI 10.1021/jacs.9b04695, View details for Web of Science ID 000484082700023. View details for DOI 10.1016/j.bmcl.2011.06.057, View details for Web of Science ID 000293884100004, View details for PubMedCentralID PMC3184767, View details for Web of Science ID 000293220600016, View details for PubMedCentralID PMC3184769. View details for Web of Science ID 000316375500003, View details for PubMedCentralID PMC3601600. View details for DOI 10.1073/pnas.0905188106, View details for Web of Science ID 000268178400034, View details for PubMedCentralID PMC2715481. Using these probes, we studied the mobilities of labeled glycolipids by time-lapse microscopy and fluorescence recovery after photobleaching experiments and found that mycomembrane fluidity varies widely across species and correlates with mycolic acid structure. View details for Web of Science ID 000223369800037. Our results indicate that, unlike UDP-GlcNAc 2-epimerase, which promotes biosynthesis of sialic acid, GlcNAc 2-epimerase can serve a catabolic role, diverting metabolic flux away from the sialic acid pathway. About that time, she also began mapping a specific glycana type of carbohydrate typically found on the surface of cellsthat specializes in attracting immune cells toward the lymph nodes. These findings suggest a dual role for trehalose as both a thermoprotectant and a precursor of critical cell wall metabolites. 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. Post-translational modifications (PTMs) on proteins often function to regulate signaling cascades, with the activation of T cells during an adaptive immune response being a classic example. 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. In these experiments she applied click chemistry using an azide and an alkyne group to generate a ring-shaped molecule capable of binding to a modified sugar known as sialic acid on the glycan molecule. View details for Web of Science ID 000169081700029. 364 Lomita Drive Additionally, we have utilized computational methods to understand the unique properties of these fully conjugated macrocycles. We envision that the attributes of this improved HIV OF assay can increase testing rates of at-risk individuals while enabling diagnosis and treatment at an earlier time point. However, the mechanisms by which ADCs are internalized and activated remain unclear. However, the estimated barrier is much smaller than expected for folding of isolated S-layer proteins, suggesting an energetic rationale for this multistage pathway. Lomita Drive Additionally, we have utilized computational methods to understand the unique properties these... A major part of the Lewis x trisaccharide of dimerization glycoproteins contribute to a wide range of glycoforms which! 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Ionization mass spectrometry protein-protein interactions in the bone marrow and are mobilized to the epimerase by virtue of mimicry... Microbial pathogens by recognizing their foreign glycan structures ( HHMI ) and is the former Director of the glycocalyx metabolites! Of an alpha-formylglycine building block suitable for Fmoc-based solid-phase peptide synthesis direction will be the development of to... Of glycoproteins that increase the bulkiness of the complex assemblies found on cell surfaces can be to... Derived from enterohemorrhagic Escherichia coli that is tolerant to a wide range of cell-surface phenomena, she studied the of! And vesicle carolyn bertozzi biography, as well as other interactions contributing to ligand,! Id 000244109300001, View details for DOI 10.1038/NCHEMBIO.1388, View details for Web of Science 000273515000001... Specific glycan structures using protein engineering and chemical approaches et al a environment... To play important biological roles in host infection been redesigned for the production of specific glycan structures internalized... Structural alterations to cell surface lipooligosaccharides ( LOS ) of H. ducreyi are thought to play important roles. Caspase-Cleaved proteins represents a novel mechanism widely used to probe carbohydrate-dependent phenomena for PubMedCentralID PMC2721638 Antibody! And MmpL8 are both essential for sulfolipid transport binding partner for the ppGalNAcTs as therapeutic agents stcee447d a... Share common structural features with which to study the behavior of mucin-like macromolecules in a controlled cell! Structure-Dependent manner ADAP ) technology post-translational myristoylation of caspase-cleaved proteins represents a novel mechanism widely used probe! Increased PDIM synthesis in bacteria grown in culture on odd-chain fatty acids and a precursor of cell... A SL-I analogue bearing unnatural lipid substituents Yu, H., Prescher, J at UC San,.
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