Context and complexity: The next big thing in synthetic glycobiology

Current Opinion in Chemical Biology

Volumn 17, Issue 6, 2013, Pages 990-996

  Lowary, Todd L ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARABINOGALACTAN; FUCOSYLTRANSFERASE; GALACTOSYLTRANSFERASE; GLYCAN DERIVATIVE; GLYCOLIPID; GLYCOPROTEIN; GUANOSINE DIPHOSPHATE; N ACETYLGLUCOSAMINYLTRANSFERASE; OLIGOSACCHARIDE; PHENOLIC GLYCOLIPID; POLYSACCHARIDE; SIALYLTRANSFERASE; URIDINE DIPHOSPHATE;

CARBOHYDRATE SYNTHESIS; ENZYME SYNTHESIS; GLYCOBIOLOGY; GLYCOPROTEIN SYNTHESIS; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPOGENESIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PEPTIDE SYNTHESIS; PROTEIN SECONDARY STRUCTURE; REVIEW; SOLID PHASE SYNTHESIS;

AMINO ACID SEQUENCE; ANIMALS; CARBOHYDRATE SEQUENCE; GLYCOMICS; GLYCOPROTEINS; HUMANS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; POLYSACCHARIDES; SYNTHETIC BIOLOGY;

EID: 84890248142     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2013.10.009     Document Type: Review

References (45)

1. Kiessling L.L., Splain R.A. Chemical approaches to glycobiology. Annu Rev Biochem 2010, 79:619-653.
2. Avci F.Y., Li X., Tsuji M., Kasper D.L. A mechanism for glycoconjugate vaccine activation of the adaptive immune system and its implications for vaccine design. Nat Med 2011, 17:1602-1609.
3. Berti F., Adamo R. Recent mechanistic insights on glycoconjugate vaccines and future perspectives. ACS Chem Biol 2013, 8:1653-1663.
4. Tanaka H., Kawai T., Adachi Y., Hanashima S., Yamaguchi Y., Ohno N., Takahashi T: Synthesis of β-(1→3) oligoglucans exhibiting a dectin-1 binding affinity and their biological evaluation. Bioorg Med Chem 2012, 20:3898-3914.
5. Greenfield L.K., Whitfield C: Synthesis of lipopolysaccharide O-antigens by ABC transporter-dependent pathways. Carbohydr Res 2012, 356:12-24.
6. Muthana S., Cao H., Chen X: Recent progress in chemical and chemoenzymatic synthesis of carbohydrates. Curr Opin Chem Biol 2009, 13:573-581.
7. Palcic MM: Glycosyltransferases as biocatalysts. Curr Opin Chem Biol 2011, 15:226-233.
8. Cobucci-Ponzano B., Strazzulli A., Rossi M., Moracci M: Glycosynthases in biocatalysis. Adv Synth Catal 2011, 353:2284-2290.
9. Schmaltz R.M., Hanson S.R., Wong CH: Enzymes in the synthesis of glycoconjugates. Chem Rev 2011, 111:4259-4260.
10. Tefsen B., Van Die I: Glycosyltransferases in chemo-enzymatic synthesis of oligosaccharides. Methods Mol Biol 2013, 1022:357-367.
11. Blixt O., Head S., Mondala T., Scanlan C., Huflejt M.E., Alvarez R., Bryan M.C., Fazio F., Calarese D., Stevens J., et al. Printed covalent glycan array for ligand profiling of diverse glycan binding proteins. Proc Natl Acad Sci U S A 2004, 101:17033-17040.
12. Koizumi A., Matsuo I., Takatani M., Seko A., Hachisu M., Takeda Y., Ito Y: Top-down chemoenzymatic approach to a high-mannose-type glycan library: synthesis of a common precursor and its enzymatic trimming. Angew Chem Int Ed 2013, 52:7426-7431.
13. Amin M.N., McLellan J.S., Huang W., Orwenyo J., Burton D.R., Koff W.C., Kwong P.D., Wang L-X: Synthetic glycopeptides reveal the glycan specificity of HIV-neutralizing antibodies. Nat Chem Biol 2013, 9:521-526.
14. Wang LX: The amazing transglycosylation activity of endo-β-N-acetylglucosaminidases. Trends Glycosci Glycotechnol 2011, 23:33-52.
15. Wang L.X., Huang W: Enzymatic transglycosylation for glycoconjugate synthesis. Curr Opin Chem Biol 2009, 13:592-600.
16. Wang Z., Chinoy Z.S., Ambre S.G., Peng W., McBride R., de Vries R.P., Glushka J., Paulson J.C., Boons G.J. A general strategy for the chemoenzymatic synthesis of asymmetrically branched N-glycans. Science 2013, 341:379-383.
17. Unverzagt C., Kajihara Y. Chemical assembly of N-glycoproteins: a refined toolbox to address a ubiquitous posttranslational modification. Chem Soc Rev 2013, 42:4408-4410.
18. Szenajch J., Wcislo G., Jeong J.Y., Szczylik C., Feldman L. The role of erythropoietin and its receptor in growth, survival and therapeutic response of human tumor cells From clinic to bench - a critical review. Biochim Biophys Acta Rev Cancer 2010, 1806:82-95.
19. Wan Q., Danishefsky S.J. Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides. Angew Chem Intl Ed 2007, 46:9248-9250.
20. Hackenberger C.P.R., Schwarzer D. Chemoselective ligation and modification strategies for peptides and proteins. Angew Chem Int Ed 2008, 47:10030-10074.
21. Wilson R.M., Dong S., Wang P., Danishefsky S.J. The winding pathway to erythropoietin along the chemistry-biology frontier: a success at last. Angew Chem Int Ed 2013, 52:7646-7650.
22. Murakami M., Okamoto R., Izumi M., Kajihara Y. Chemical synthesis of an erythropoietin glycoform containing a complex-type disialyloligosaccharide. Angew Chem Int Ed 2012, 51:3567-3571.
23. Kajihara Y., Suzuki Y., Yamamoto N., Sasaki K., Sakakibara T., Juneja L.R. Prompt chemoenzymatic synthesis of diverse complext-type oligosaccharides and its application to the solid-phase synthesis of a glycopeptide with Asn-linked sialyl-undeca- and asialo-nonasaccharides. Chem Eur J 2004, 10:971-985.
24. Sakamoto I., Tezuka K., Fukae K., Ishii K., Taduru K., Maeda M., Ouchi M., Yoshida K., Nambu Y., Igarashi J., et al. Chemical synthesis of homogeneous human glycosyl-interferon-β that exhibits potent antitumor activity in vivo. J Am Chem Soc 2012, 134:5428-5430.
25. Wang P., Dong S., Brailsford J.A., Iyer K., Townsend S.D., Zhang Q., Hendrickson R.C., Shieh J., Moore M.A.S., Danishefsky S.J. At last: erythropoietin as a single glycoform. Angew Chem Int Ed 2012, 51:11576-11584.
26. Wang P., Aussedat B., Vohra Y., Danishefsky S.J. An advance in the chemical synthesis of homogeneous N-linked glycopolypeptides by convergent aspartylation. Angew Chem Intl Ed 2012, 51:11571-11575.
27. Matsuzaki Y., Ito Y., Nakahara Y., Ogawa T. Synthesis of branched poly-N-acetyl-lactosamine type pentaantennary pentacosasaccharide: glycan part of a glycosyl ceramide from rabbit erythrocyte membrane. Tetrahedron Lett 1993, 34:1061-1070.
28. Pozsgay V. Synthetic Shigella vaccines: a carbohydrate-protein conjugate with totally synthetic hexadecasaccharide haptens. Angew Chem Int Ed 1998, 37:138-142.
29. Petitou M., Duchaussoy P., Driguez P.A., Hérault J.P., Lormeau J.C., Herbert J.M. New synthetic heparin mimetics able to inhibit thrombin and factor Xa. Bioorg Med Chem Lett 1999, 9:1155-1160.
30. Pozsgay V. A new strategy in oligosaccharide synthesis using lipophilic protecting groups: synthesis of a tetracosasaccharide. Tetrahedron Asymm 2000, 11:151-172.
31. Holemann A., Stocker B.L., Seeberger P.H. Synthesis of a core arabinomannan oligosaccharide of Mycobacterium tuberculosis. J Org Chem 2006, 71:8071-8080.
32. Fraser-Reid B., Lu J., Jayaprakash K.N., Lopez J.C. Synthesis of a 28-mer oligosaccharide core of mycobacterial lipoarabinomannan (LAM) requires only two n-pentenyl orthoester progenitors. Tetrahedron Asymm 2006, 17:2449-2450.
33. Joe M., Bai Y., Nacario R.C., Lowary T.L. Synthesis of the docosanasaccharide arabinan domain of mycobacterial arabinogalactan and a proposed octadecasaccharide biosynthetic precursor. J Am Chem Soc 2007, 129:9885-9890.
34. Pozsgay V. Recent developments in synthetic oligosaccharide-based bacterial vaccines. Curr Top Med Chem 2008, 8:126-140.
35. Ishiwata A., Ito Y: Synthesis of docosasaccharide arabinan motif of mycobacterial cell wall. J Am Chem Soc 2011, 133:2275-2291.
36. Pozsgay V., Kubler-Kielb J., Coxon B., Santacroce P., Robbins J.B., Schneerson R: Synthetic oligosaccharides as tools to demonstrate cross-reactivity between polysaccharide antigens. J Org Chem 2012, 77:5922-5930.
37. Liu L., Bai Y., Sun N., Xia L., Lowary T.L., Klassen JS: Carbohydrate-lipid interactions: affinities of methylmannose polysaccharides for lipids in aqueous solution. Chem Eur J 2012, 18:12059-12067.
38. Cheon H.S., Lian Y., Kishi Y. Highly stereoselective and iterative synthesis of α-(1→4)-linked polysaccharides composed of 3-O-methyl-d-mannose. Org Lett 2007, 9:3323-3330.
39. Hsu M.C., Lee J., Kishi Y: Synthetic 3-O-methylmannose-containing polysaccharides (sMMPs): design and synthesis. J Org Chem 2007, 72:1931-1940.
40. Meppen M., Wang Y., Cheon H.S., Kishi Y: Synthetic 6-O-methylglucose-containing polysaccharides (sMGPs): design and synthesis. J Org Chem 2007, 72:1941-1950.
41. Calin O., Eller S., Seeberger PH: Automated polysaccharide synthesis: assembly of a 30 mer mannoside. Angew Chem Int Ed 2013, 52:5862-5865.
42. Kent S., Sohma Y., Liu S., Bang D., Pentelute B., Mandal K: Through the looking glass - a new world of proteins enabled by chemical synthesis. J Pept Sci 2012, 18:428-436.
43. DeMarco M.L., Woods RJ: Structural glycobiology: a game of snakes and ladders. Glycobiology 2008, 18:426-440.
44. Barroso S., Castelli R., Baggelaar M.P., Geerdink D., Ter Horst B., Casas-Arce E., Overkleeft H.S., van der Marel G.A., Codee J.D.C., Minnaard AJ: Total synthesis of the triglycosyl phenolic glycolipid PGL-tb1 from Mycobacterium tuberculosis. Angew Chem Int Ed 2012, 51:11774-11777.
45. Varki A., Cummings R.D., Esko J.D., Freeze H.H., Stanley P., Marth J.D., Bertozzi C.R., Hart G.W., Etzler ME: Symbol nomenclature for glycan representation. Proteomics 2009, 9:5398-5400.