Abstract
Seven analogues of p-nitrophenyl T-antigen [Galβ(1→3)GalNAcα(1→O)PNP] have been synthesized as potential substrates for elucidation of the substrate specificity of endo-α-N-acetylgalactosaminidase. These compounds, which are commercially unavailable, include: GlcNAcβ(1→3){GlcNAcβ(1→6)}GalNAcα(1→O)PNP [core 4 type], GalNAcα(1→3)GalNAcα(1→O)PNP [core 5 type], GlcNAcβ(1→6)GalNAcα(1→O)PNP [core 6 type], GalNAcα(1→6)GalNAcα(1→O)PNP [core 7 type], Galα(1→3)GalNAcα(1→O)PNP [core 8 type], Glcβ(1→3)GalNAcα(1→O)PNP and GalNAcβ(1→3)GalNAcα(1→O)PNP. The assembly of these synthetic probes was accomplished efficiently, based on di-tert-butylsilylene(DTBS)-directed α-galactosylation as a key reaction.
Similar content being viewed by others
References
Tanaka, Y., Takahashi, Y., Shinose, M., Omura, S., Karakasa, I., Iwase, H., Hotta, K.: Screening and fermentation of endo-α-N-acetylgalactosaminidase S, a mucin-hydrolyzing enzyme from Streptomyces acting on the GalNAc-O-Ser (Thr) linkage. J. Ferment. Bioeng. 85, 381–387 (1998) doi:10.1016/S0922-338X(98)80081-0
Ashida, H., Yamamoto, K., Murata, T., Usui, T., Kumagai, H.: Characterization of endo-α-N-acetylgalactosaminidase from Bacillus sp. and syntheses of neo-oligosaccharides using its transglycosylation activity. Arch. Biochem. Biophys. 373, 394–400 (2000) doi:10.1006/abbi.1999.1565
Fujita, K., Oura, F., Nagamine, N., Katayama, T., Hiratake, J., Sakata, K., et al.: Identification and molecular cloning of a novel glycoside hydrolase family of core 1 type O-glycan-specific endo-α-N-acetylgalactosaminidase from Bifidobacterium longum. J. Biol. Chem. 280, 37415–37422 (2005) doi:10.1074/jbc.M506874200
Benno, Y., Mitsuoka, T.: Impact of Bifidobacterium longum on human fecal microflora. Microbiol. Immunol. 36, 683–694 (1992)
Beutler, E., Kuhl, W.: Purification and properties of human α-galactosidases. J. Biol. Chem. 247, 7195–7200 (1972)
Casciola-Rosen, L.A.F., Hubbard, A.L.: Hydrolases in intracellular compartments of rat liver cells. J. Biol. Chem. 266, 4341–4347 (1991)
Imamura, A., Ando, H., Korogi, S., Tanabe, G., Muraoka, O., Ishida, H., et al.: Di-tert-butylsilylene (DTBS) group-directed α-selective galactosylation unaffected by C-2 participating functionalities. Tetrahedron Lett. 44, 6725–6728 (2003) doi:10.1016/S0040-4039(03)01647-2
Imamura, A., Kimura, A., Ando, H., Ishida, H., Kiso, M.: Extended applications of di-tert-butylsilylene-directed α-predominant galactosylation compatible with C2-participating groups toward the assembly of various glycosides. Chem. Eur. J. 12, 8862–8870 (2006) doi:10.1002/chem.200600832
Imamura, A., Ando, H., Ishida, H., Kiso, M.: DTBS(di-tert-butylsilylene)-directed α-galactosylation for the synthesis of biologically relevant glycans. Curr. Org. Chem. 12, 675–689 (2008) doi:10.2174/138527208784577358
Kunz, H., Birnbach, S., Wernig, P.: Synthesis of glycopeptides with the Tn and T antigen structures, and their coupling to bovine serum albumin. Carbohydr. Res. 202, 207–223 (1990) doi:10.1016/0008-6215(90)84081-5
Geiger, J., Reddy, B.G., Winterfeld, G.A., Weber, R., Przybylski, M., Schmidt, R.R.: Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis. J. Org. Chem. 72, 4367–4377 (2007) doi:10.1021/jo061670b
Gambert, U., Thiem, J.: Chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant. Carbohydr. Res. 299, 85–89 (1997) doi:10.1016/S0008-6215(96)00324-2
Bongat, A.F.G., Demchenko, A.V.: Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars. Carbohydr. Res. 342, 374–406 (2007) doi:10.1016/j.carres.2006.10.021
Greene, T.W., Wuts, P.G.M. (eds.): Protective Groups in Organic Chemistry 4th ed., Wiley, New York (2007)
Matsumoto, T., Katsuki, M., Suzuki, K.: Rapid O-glycosylation of phenols with glycosyl fluoride by using the combinational activator, Cp2HfCl2–AgClO4. Chem. Lett. 437–440 (1989) doi:10.1246/cl.1989.437
Yamaguchi, M., Horiguchi, A., Fukuda, A., Minami, T.: Novel synthesis of aryl 2,3,4,6-tetra-O-acetyl-d-glucopyranodides. J. Chem. Soc., Perkin Trans. 1, 1079–1082 (1990) doi:10.1039/p19900001079
Lee, Y.-S., Rho, E.-S., Min, Y.-K., Kim, B.-T., Kim, K.-H.: Practical β-stereoselective O-glycosylation of phenols with penta-O-acetyl-β-d-glucopyranose. J. Carbohydr. Chem. 20, 503–506 (2001) doi:10.1081/CAR-100106933
Furusawa, K.: Removal of cyclic di-t-butylsilanediyl protecting groups using tributylamine hydrofluoride (TBAHF) reagent. Chem. Lett. 509–510 (1989) doi:10.1246/cl.1989.509
Veeneman, G.H., van Leeuwen, S.H., van Boom, J.H.: Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters. Tetrahedron Lett. 31, 1331–1334 (1990) doi:10.1016/S0040-4039(00)88799-7
Schmidt, R.R.: New methods for the synthesis of glycosides and oligosaccharides—Are there alternatives to the Koenigs–Knorr method? Angew. Chem. Int. Ed. Engl. 25, 212–235 (1986) doi:10.1002/anie.198602121
Ogawa, T., Nakabayashi, S., Sasajima, K.: Synthesis of phenyl 6-O-acyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-d-glucopyranoside. Carbohydr. Res. 95, 308–312 (1981) doi:10.1016/S0008-6215(00)85587-1
Kanie, O., Ito, Y., Ogawa, T.: Orthogonal glycosylation strategy in synthesis of extended blood group B determinant. Tetrahedron Lett. 37, 4551–4554 (1996) doi:10.1016/0040-4039(96)00901-X
Verduyn, R., Douwes, M., van der Klein, P.A.M., Mösinger, E.M., van der Marel, G.A., van Boom, J.H.: Synthesis of a methyl heptaglucoside: Analogue of the phytoalexin elicitor from phytophtora megasperma. Tetrahedron 49, 7301–7316 (1993) doi:10.1016/S0040-4020(01)87208-2
Acknowledgements
This work was financially supported by the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan (Grant-in-Aid for Scientific Research to M. K., No. 17101007), and CREST of JST (Japan Science and Technology Agency). We thank Drs. K. Yamamoto and H. Ashida of Kyoto University, Kyoto, Japan, for meaningful discussion.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Sato, T., Imamura, A., Ando, H. et al. Di-tert-butylsilylene-directed α-selective synthesis of p-nitrophenyl T-antigen analogues. Glycoconj J 26, 83–98 (2009). https://doi.org/10.1007/s10719-008-9168-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10719-008-9168-y