Chemical Probing of Glycans in Cells and Organisms

Overview

Journal Chem Soc Rev

Specialty Chemistry

Date 2012 Dec 22

PMID 23257905

Citations 15

Authors

Sara H Rouhanifard

Lars Ulrik Nordstrom

Tianqing Zheng

Peng Wu

Affiliations

Soon will be listed here.

Abstract

Among the four major building blocks of life, glycans play essential roles in numerous physiological and pathological processes. Due to their non-templated biosynthesis, advances towards elucidating the molecular details of glycan functions are relatively slow compared with the pace of protein and nucleic acid research. Over the past 30 years, chemical tools have emerged as powerful allies to genetics and molecular biology in the study of glycans in their native environment. This tutorial review will provide an overview of the recent technological developments in the field, as well as the progress in the application of these techniques to probe glycans in cells and organisms.

Citing Articles

Chemoenzymatic Measurement of LacNAc in Single-Cell Multiomics Reveals It as a Cell-Surface Indicator of Glycolytic Activity of CD8 T Cells.

Yu W, Zhao X, Jalloh A, Li Y, Zhao Y, Dinner B J Am Chem Soc. 2023; 145(23):12701-12716.

PMID: 37276352 PMC: 10733619. DOI: 10.1021/jacs.3c02602.

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate.

Ling T, Boyd L, Rivas F Chem Res Toxicol. 2022; 35(4):569-584.

PMID: 35312315 PMC: 9019815. DOI: 10.1021/acs.chemrestox.1c00428.

SuFExable polymers with helical structures derived from thionyl tetrafluoride.

Li S, Li G, Gao B, Pujari S, Chen X, Kim H Nat Chem. 2021; 13(9):858-867.

PMID: 34400816 PMC: 8713280. DOI: 10.1038/s41557-021-00726-x.

Glycan-protein cross-linking mass spectrometry reveals sialic acid-mediated protein networks on cell surfaces.

Xie Y, Chen S, Li Q, Sheng Y, Alvarez M, Reyes J Chem Sci. 2021; 12(25):8767-8777.

PMID: 34257876 PMC: 8246274. DOI: 10.1039/d1sc00814e.

Decorating bacteria with self-assembled synthetic receptors.

Lahav-Mankovski N, Prasad P, Oppenheimer-Low N, Raviv G, Dadosh T, Unger T Nat Commun. 2020; 11(1):1299.

PMID: 32157077 PMC: 7064574. DOI: 10.1038/s41467-020-14336-7.

References

Tornoe C, Christensen C, Meldal M . Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem. 2002; 67(9):3057-64. DOI: 10.1021/jo011148j. View

Hanson S, Hsu T, Weerapana E, Kishikawa K, Simon G, Cravatt B . Tailored glycoproteomics and glycan site mapping using saccharide-selective bioorthogonal probes. J Am Chem Soc. 2007; 129(23):7266-7. PMC: 2552998. DOI: 10.1021/ja0724083. View

Sampathkumar S, Li A, Jones M, Sun Z, Yarema K . Metabolic installation of thiols into sialic acid modulates adhesion and stem cell biology. Nat Chem Biol. 2006; 2(3):149-52. DOI: 10.1038/nchembio770. View

Boyce M, Carrico I, Ganguli A, Yu S, Hangauer M, Hubbard S . Metabolic cross-talk allows labeling of O-linked beta-N-acetylglucosamine-modified proteins via the N-acetylgalactosamine salvage pathway. Proc Natl Acad Sci U S A. 2011; 108(8):3141-6. PMC: 3044403. DOI: 10.1073/pnas.1010045108. View

Laughlin S, Baskin J, Amacher S, Bertozzi C . In vivo imaging of membrane-associated glycans in developing zebrafish. Science. 2008; 320(5876):664-7. PMC: 2701225. DOI: 10.1126/science.1155106. View

Backus K, Boshoff H, Barry C, Boutureira O, Patel M, DHooge F . Uptake of unnatural trehalose analogs as a reporter for Mycobacterium tuberculosis. Nat Chem Biol. 2011; 7(4):228-35. PMC: 3157484. DOI: 10.1038/nchembio.539. View

Baskin J, Prescher J, Laughlin S, Agard N, Chang P, Miller I . Copper-free click chemistry for dynamic in vivo imaging. Proc Natl Acad Sci U S A. 2007; 104(43):16793-7. PMC: 2040404. DOI: 10.1073/pnas.0707090104. View

Gordon C, Mackey J, Jewett J, Sletten E, Houk K, Bertozzi C . Reactivity of biarylazacyclooctynones in copper-free click chemistry. J Am Chem Soc. 2012; 134(22):9199-208. PMC: 3368396. DOI: 10.1021/ja3000936. View

Zheng T, Jiang H, Gros M, Del Amo D, Sundaram S, Lauvau G . Tracking N-acetyllactosamine on cell-surface glycans in vivo. Angew Chem Int Ed Engl. 2011; 50(18):4113-8. PMC: 3136350. DOI: 10.1002/anie.201100265. View

10.

Breidenbach M, Palaniappan K, Pitcher A, Bertozzi C . Mapping yeast N-glycosites with isotopically recoded glycans. Mol Cell Proteomics. 2012; 11(6):M111.015339. PMC: 3433913. DOI: 10.1074/mcp.M111.015339. View

11.

Apweiler R, Hermjakob H, Sharon N . On the frequency of protein glycosylation, as deduced from analysis of the SWISS-PROT database. Biochim Biophys Acta. 1999; 1473(1):4-8. DOI: 10.1016/s0304-4165(99)00165-8. View

12.

Keppler O, Stehling P, Herrmann M, Kayser H, Grunow D, REUTTER W . Biosynthetic modulation of sialic acid-dependent virus-receptor interactions of two primate polyoma viruses. J Biol Chem. 1995; 270(3):1308-14. DOI: 10.1074/jbc.270.3.1308. View

13.

Dehnert K, Beahm B, Huynh T, Baskin J, Laughlin S, Wang W . Metabolic labeling of fucosylated glycans in developing zebrafish. ACS Chem Biol. 2011; 6(6):547-52. PMC: 3117394. DOI: 10.1021/cb100284d. View

14.

Takano R, Muchmore E, Dennis J . Sialylation and malignant potential in tumour cell glycosylation mutants. Glycobiology. 1994; 4(5):665-74. DOI: 10.1093/glycob/4.5.665. View

15.

Wang W, Hong S, Tran A, Jiang H, Triano R, Liu Y . Sulfated ligands for the copper(I)-catalyzed azide-alkyne cycloaddition. Chem Asian J. 2011; 6(10):2796-802. PMC: 3568503. DOI: 10.1002/asia.201100385. View

16.

Besanceney-Webler C, Jiang H, Zheng T, Feng L, Del Amo D, Wang W . Increasing the efficacy of bioorthogonal click reactions for bioconjugation: a comparative study. Angew Chem Int Ed Engl. 2011; 50(35):8051-6. PMC: 3465470. DOI: 10.1002/anie.201101817. View

17.

Sawa M, Hsu T, Itoh T, Sugiyama M, Hanson S, Vogt P . Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo. Proc Natl Acad Sci U S A. 2006; 103(33):12371-6. PMC: 1567886. DOI: 10.1073/pnas.0605418103. View

18.

Coyne M, Reinap B, Lee M, Comstock L . Human symbionts use a host-like pathway for surface fucosylation. Science. 2005; 307(5716):1778-81. DOI: 10.1126/science.1106469. View

19.

Gahmberg C, Andersson L . Selective radioactive labeling of cell surface sialoglycoproteins by periodate-tritiated borohydride. J Biol Chem. 1977; 252(16):5888-94. View

20.

Xie R, Hong S, Feng L, Rong J, Chen X . Cell-selective metabolic glycan labeling based on ligand-targeted liposomes. J Am Chem Soc. 2012; 134(24):9914-7. DOI: 10.1021/ja303853y. View