Thio-click approach to the synthesis of stable glycomimetics

References

Acton, E.M., Goerner, R. N., Uh, H. S., Ryan, K. J., Henry, D. W., Cass, C. E., & LePage, G. A. (1979). Improved antitumor effects in 3_-branched homologs of 2_-deoxythioguanine. Synthesis and evaluation of thioguanine nucleosides of 2,3- dideoxy-3-(hydroxymethyl)-D-erythro-pentofuranose. Journal of Medicinal Chemistry, 22, 518-525. DOI: 10.1021/jm0 0191a012.Search in Google Scholar

Chakka, N., Johnston, B. D., & Pinto, B. M. (2005). Synthesis and conformational analysis of disaccharide analogues containing disulfide and selenosulfide functionalities in the interglycosidic linkages. Canadian Journal of Chemistry, 83, 929-936. DOI: 10.1139/v05-107.10.1139/v05-107Search in Google Scholar

Dénès, F., Pichowicz, M., Povie, G., & Renaud, P. (2014). Thiyl radicals in organic synthesis. Chemical Reviews, 114, 2587-2693. DOI: 10.1021/cr400441m.10.1021/cr400441mSearch in Google Scholar PubMed

Dondoni, A., & Marra, A. (2012). Recent applications of thiol- ene coupling as a click process for glycoconjugation. Chemical Society Reviews, 41, 573-586. DOI: 10.1039/c1cs15157f.10.1039/C1CS15157FSearch in Google Scholar PubMed

Ernst, B., & Magnani, J. L. (2009). From carbohydrate leads to glycomimetic drugs. Nature Reviews Drug Discovery, 8, 661-677. DOI: 10.1038/nrd2852.10.1038/nrd2852Search in Google Scholar PubMed PubMed Central

Fiore, M., Marra, A., & Dondoni, A. (2009). Photoinduced thiol-ene coupling as a click ligation tool for thiodisaccharide synthesis. Journal of Organic Chemistry, 74, 4422-4425. DOI: 10.1021/jo900514w.10.1021/jo900514wSearch in Google Scholar PubMed

Illyés, T. Z., Szabó, T., & Szilágyi, L. (2011). Glycosylation via mixed disulfide formation using glycosylthiophthalimides and -succinimides as glycosylsulfenyl-transfer reagents. Carbohydrate Research, 346, 1622-1627. DOI: 10.1016/j.carres.2011.04.020.10.1016/j.carres.2011.04.020Search in Google Scholar PubMed

Lázár, L., Csávás, M., Herczeg, M., Herczegh, P., & Borbás, A. (2012). Synthesis of S-linked glycoconjugates and S-disaccharides by thiol-ene coupling reaction of enoses. Organic Letters, 14, 4650-4653. DOI: 10.1021/ol302098u.10.1021/ol302098uSearch in Google Scholar PubMed

Lázár, L., Csávás,M., Hadházi, Á.,Herczeg,M., Tóth,M., Somsák, L., Barna, T., Herczegh, P., & Borbás, A. (2013). Systematic study on free radical hydrothiolation of unsaturated monosaccharide derivatives with exo- and endocyclic double bonds. Organic & Biomolecular Chemistry, 11, 5339-5350. DOI: 10.1039/c3ob40547h.10.1039/c3ob40547hSearch in Google Scholar PubMed

Liu, L., McKee, M., & Postema, M. H. D. (2001). Synthesis of C-saccharides and higher congeners. Current Organic Chemistry, 5, 1133-1167. DOI: 10.2174/1385272013374699.10.2174/1385272013374699Search in Google Scholar

Lopez, M., Bornaghi, L. F., Driguez, H., & Poulsen, S. A. (2011). Synthesis of sulfonamide-bridged glycomimetics. The Journal of Organic Chemistry, 76, 2965-2975. DOI: 10.1021/jo2001269.10.1021/jo2001269Search in Google Scholar PubMed

Matta, K. L., Girotra, R. N., & Barlow, J. J. (1975). Synthesis of p-nitrobenzyl and p-nitrophenyl 1-thioglycopyranosides. Carbohydrate Research, 43, 101-109. DOI: 10.1016/s0008-6215(00)83976-2.10.1016/S0008-6215(00)83976-2Search in Google Scholar

Mugunthan, G., Sriram, D., Yogeeswari, P., & Kartha, K. P. R. (2011). Synthetic analogues of mycobacterial arabinogalactan linkage-disaccharide part II: Synthesis and preliminary screening of lipophilic O-alkyl glycosides. Carbohydrate Research, 346, 2401-2405. DOI: 10.1016/j.carres.2011.08.027.10.1016/j.carres.2011.08.027Search in Google Scholar

Praly, J. P. (2000). Structure of anomeric glycosyl radicals and their transformations under reductive conditions. Advances in Carbohydrate Chemistry and Biochemistry, 56, 65-151. DOI: 10.1016/s0065-2318(01)56003-5.10.1016/S0065-2318(01)56003-5Search in Google Scholar

Prosperi, D., Ronchi, S., Lay, L., Rencurosi, A., & Russo, G. (2004). Efficient synthesis of unsymmetrical ureidolinked disaccharides. European Journal of Organic Chemistry, 2004, 395-405. DOI: 10.1002/ejoc.200300483.10.1002/ejoc.200300483Search in Google Scholar

Robina, I., Vogel, P., & Witczak, Z. (2001). Synthesis and biological properties of monothiosaccharides. Current Organic Chemistry, 5, 1177-1214. DOI: 10.2174/1385272013374743.10.2174/1385272013374743Search in Google Scholar

Staderini, S., Chambery, A., Marra, A., & Dondoni, A. (2012). Free-radical hydrothiolation of glycals: A thiol-ene-based synthesis of S-disaccharides. Tetrahedron Letters, 53, 702-704. DOI: 10.1016/j.tetlet.2011.11.140.10.1016/j.tetlet.2011.11.140Search in Google Scholar

Stellenboom, N., Hunter, R., & Caira, M. R. (2010). One-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole as oxidant: Interception of the sulfenyl chloride intermediate. Tetrahedron, 66, 3228-3241. DOI: 10.1016/j.tet.2010. 02.077.Search in Google Scholar

Szilágyi, L., Illyés, T. Z., & Herczegh, P. (2001). Elaboration of a novel type of interglycosidic linkage: Syntheses of disulfide disaccharides. Tetrahedron Letters, 42, 3901-3903. DOI: 10.1016/s0040-4039(01)00578-0.10.1016/S0040-4039(01)00578-0Search in Google Scholar

Szilágyi, L., & Varela, O. (2006). Non-conventional glycosidic linkages: Syntheses and structures of thiooligosaccharides and carbohydrates with three-bond glycosidic connections. Current Organic Chemistry, 10, 1745-1770. DOI: 10.2174/138527206778249874.10.2174/138527206778249874Search in Google Scholar

Tóth, M., & Somsák, L. (2001). exo-Glycals from glycosyl cyanides. First generation of C-glycosylmethylene carbenes from 2,5- and 2,6-anhydroaldose tosylhydrazones. Journal of the Chemical Society, Perkin Transactions 1, 942-943. DOI: 10.1039/b102963k.10.1039/b102963kSearch in Google Scholar

Tóth, M., K¨ovér, K. E., Bényei, A., & Somsák, L. (2003). CGlycosylmethylene carbenes: Synthesis of anhydro-aldose tosylhydrazones as precursors; generation and a new synthetic route to exo-glycals. Organic & Biomolecular Chemistry, 1, 4039-4046. DOI: 10.1039/b307378e.10.1039/B307378ESearch in Google Scholar PubMed

Tóth, M., Kun, S., Somsák, L., & Goyard, D 2011) Preparation of exo-glycals from 2,6-anhydro-aldose-tosylhydrazones. In P. Kovac (Ed.) Carbohydrate chemistry: Proven synthetic methods (pp. 365-373). Boca Raton, FL, USA: CRC Press.Search in Google Scholar

Witczak, Z. J., & Culhane, J. M. (2005). Thiosugars: New perspectives regarding availability and potential biochemical and medicinal applications. Applied Microbiology and Biotechnology, 69, 237-244. DOI: 10.1007/s00253-005-0156- x.Search in Google Scholar

Witczak, Z. J., Lorchak, D., & Nguyen, N. (2007). A click chemistry approach to glycomimetics: Michael addition of 2,3,4,6-tetra-O-acetyl-1-thio-β-_-glucopyranose to 4-deoxy-1,2-O-isopropylidene-_-glycero-pent-4-enopyranos-3-ulose - a convenient route to novel 4-deoxy-(1→5)-5-C-thiodisaccharides. Carbohydrate Research, 342, 1929-1931. DOI: 10.1016/j.carres.2007.06.005.10.1016/j.carres.2007.06.005Search in Google Scholar PubMed

Witczak, Z. J., & Bielski, R. (2013). Click chemistry in glycoscience: New developments and strategies. New York, NY, USA: Wiley. 10.1002/9781118526996Search in Google Scholar