Synthesis of the Non Reducing End Oligosaccharides of Glycosphingolipids from Ascaris suum
Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1...
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| Published in | Chemical & pharmaceutical bulletin Vol. 67; no. 2; pp. 143 - 154 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
TOKYO
The Pharmaceutical Society of Japan
01.02.2019
Pharmaceutical Society of Japan Pharmaceutical Soc Japan Japan Science and Technology Agency |
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| Abstract | Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (4) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (5) (R = biotinylated probe) were synthesized by stepwise condensation (1–4) and block synthesis (5) using 5-(methoxycarbonylpentyl) 2-O-benzoyl-3-O-2-napthylmethyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside (12) as a common precursor. Compound 12 was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively. |
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| AbstractList | Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3) Galα1→3GalNAcβ1→OR (4) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (5) (R = biotinylated probe) were synthesized by stepwise condensation (1-4) and block synthesis (5) using 5-(methoxycarbonylpentyl) 2-O-benzoyl-3-O-2-napthylmethyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside (12) as a common precursor. Compound 12 was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively. Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (4) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (5) (R = biotinylated probe) were synthesized by stepwise condensation (1-4) and block synthesis (5) using 5-(methoxycarbonylpentyl) 2-O-benzoyl-3-O-2-napthylmethyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside (12) as a common precursor. Compound 12 was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively.Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (4) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (5) (R = biotinylated probe) were synthesized by stepwise condensation (1-4) and block synthesis (5) using 5-(methoxycarbonylpentyl) 2-O-benzoyl-3-O-2-napthylmethyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside (12) as a common precursor. Compound 12 was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively. Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Gal alpha 1 -> 3GalNAc beta 1 -> OR (1), Gal beta 1 -> 3Gal alpha 1 -> 3GalNAc beta 1 -> OR (2), Gal beta 1 -> 6Gal alpha 1 -> 3GalNAc beta 1 -> OR (3), Gal beta 1 -> 6(Gal beta 1 -> 3) Gal alpha 1 -> 3GalNAc beta 1 -> OR (4) and GlcNAc beta 1 -> 6Gal beta 1 -> 6(Gal beta 1 -> 3)Gal alpha 1 -> 3GalNAc beta 1 -> OR (5) (R = biotinylated probe) were synthesized by stepwise condensation (1-4) and block synthesis (5) using 5-(methoxycarbonylpentyl) 2-O-benzoyl-3-O-2-napthylmethyl-4,6-O-di-tert-butylsilylene-alpha-D-galactopyranosyl-(1 -> 3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-galactopyranoside (12) as a common precursor. Compound 12 was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively. Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (4) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (5) (R = biotinylated probe) were synthesized by stepwise condensation (1–4) and block synthesis (5) using 5-(methoxycarbonylpentyl) 2-O-benzoyl-3-O-2-napthylmethyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside (12) as a common precursor. Compound 12 was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively. Graphical Abstract |
| Author | Kumada, Hiromi Kiuchi, Fumiyuki Umeda, Yuna Yamano, Kimiaki Shimazaki, Yoshinori Schweizer, Frank Oshima, Naohiro Takeda, Tadahiro Hada, Noriyasu |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30713275$$D View this record in MEDLINE/PubMed |
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| Copyright | 2019 The Pharmaceutical Society of Japan Copyright Japan Science and Technology Agency 2019 |
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| Keywords | GLYCOSIDES ANTIGENICITY ASSAY STRUCTURAL ELUCIDATION HUMAN SERA host-parasite interaction glycosphingolipid biotin probe NEMATODE PROTOSTOMIA PHYLA SYNTHESIS stereocontrolled synthesis Ascaris suum CARBOHYDRATE MOIETIES host–parasite interaction |
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| References | 13) Ohtsuka I., Hada N., Ohtaka H., Sugita M., Takeda T., Chem. Pharm. Bull., 50, 600–604 (2002). 22) Hada N., Oka J., Nishiyama A., Takeda T., Tetrahedron Lett., 47, 6647–6650 (2006). 9) Koizumi A., Yamano K., Schweizer F., Takeda T., Kiuchi F., Hada N., Eur. J. Med. Chem., 46, 1768–1778 (2011). 24) Scaman C. H., Hindsgaul O., Palcic M. M., Srivastava O. P., Carbohydr. Res., 296, 203–213 (1996). 4) Hada N., Miyamura A., Ohtsuka I., Kiuchi F., Heterocycles, 88, 689–704 (2014). 14) Yamano K., Koizumi A., Takeda T., Kiuchi F., Hada N., Parasitol. Res., 111, 795–805 (2012). 8) Koizumi A., Yamano K., Tsuchiya T., Schweizer F., Kiuchi F., Hada N., Molecules, 17, 9023–9042 (2012). 2) Hada N., Kitamura A., Yamano K., Schweizer F., Kiuchi F., Chem. Pharm. Bull., 64, 865–873 (2016). 26) Grundler G., Schmidt R. R., Carbohydr. Res., 135, 203–218 (1985). 3) Ohtsuka I., Hada N., Kanemaru M., Fujii T., Atsumi T., Kakiuchi N., Carbohydr. Res., 404, 9–16 (2015). 23) Veeneman G. H., van Leeuwen S. H., van Boom J. H., Tetrahedron Lett., 31, 1331–1334 (1990). 5) Ohtsuka I., Hada N., Atsumi T., Kakiuchi N., Tetrahedron, 69, 1470–1475 (2013). 17) Friedl C. H., Lochnit G., Zahringer U., Bahr U., Geyer R., Biochem. J., 369, 89–102 (2003). 10) Koizumi A., Hada N., Kaburaki A., Yamano K., Schweizer F., Takeda T., Carbohydr. Res., 344, 856–868 (2009). 20) Schmidt R. R., Angew. Chem. Int. Ed. Engl., 25, 212–235 (1986). 15) Yamano K., Hada N., Yamamura T., Takeda T., Honma H., Sawada Y., J. Helminthol., 80, 387–391 (2006). 21) Xia J., Alderfer J. L., Locke R. D., Piskorz C. F., Matta K. L., J. Org. Chem., 68, 2752–2759 (2003). 6) Ozawa H., Sonoda Y., Kato S., Suzuki E., Matsuoka R., Kanaya T., Kiuchi F., Hada N., Kasahara T., Biol. Pharm. Bull., 35, 2054–2058 (2012). 16) Nakamura-Uchiyama F., Tokunaga Y., Suzuki A., Akao N., Hiromatsu K., Hitomi S., Nawa Y., Scand. J. Infect. Dis., 38, 221–224 (2006). 12) Ohtsuka I., Hada N., Sugita M., Takeda T., Carbohydr. Res., 337, 2037–2047 (2002). 19) Sabesan S., Paulson J. C., J. Am. Chem. Soc., 108, 2068–2080 (1986). 1) Kanaya T., Mashio R., Watanabe T., Schweizer F., Hada N., Tetrahedron, 73, 6847–6855 (2017). 11) Lochnit G., Dennis R. D., Ulmer A. J., Geyer R., J. Biol. Chem., 273, 466–474 (1998). 27) Marra A., Esnault J., Veyrieres A., Sinay P., J. Am. Chem. Soc., 114, 6354–6360 (1992). 25) Dasgupta F., Garegg P. J., Carbohydr. Res., 177, c13–c17 (1988). 7) Kanaya T., Schweizer F., Takeda T., Kiuchi F., Hada N., Carbohydr. Res., 361, 55–72 (2012). 18) Sarkar S. K., Roy N., J. Carbohydr. Chem., 22, 285–296 (2003). 22 23 24 25 26 27 10 11 12 13 14 15 16 17 18 19 1 2 3 4 5 6 7 8 9 20 21 Xia, J (WOS:000181953700028) 2003; 68 Ohtsuka, I (WOS:000315064600006) 2013; 69 Ozawa, H (WOS:000310662700031) 2012; 35 Ohtsuka, I (WOS:000179425500014) 2002; 337 Lochnit, G (WOS:000071295600071) 1998; 273 Hada, N (WOS:000240182400036) 2006; 47 Scaman, CH (WOS:A1996WC08700012) 1996; 296 SCHMIDT, RR (WOS:A1986C084200002) 1986; 25 Sarkar, SK (WOS:000184517500004) 2003; 22 Yamano, K (WOS:000242218000009) 2006; 80 Ohtsuka, I (WOS:000175370700007) 2002; 50 Koizumi, A (WOS:000266192500003) 2009; 344 Hada, N (WOS:000329883900049) 2014; 88 Kanaya, T (WOS:000416396000004) 2017; 73 Ohtsuka, I (WOS:000349912000002) 2015; 404 Nakamura-Uchiyama, F (WOS:000235553800015) 2006; 38 VEENEMAN, GH (WOS:A1990CT53700031) 1990; 31 MARRA, A (WOS:A1992JF87100010) 1992; 114 Kanaya, T (WOS:000310843700009) 2012; 361 GRUNDLER, G (WOS:A1985ADQ6200004) 1985; 135 Yamano, K (WOS:000306694400035) 2012; 111 DASGUPTA, F (WOS:A1988P289300036) 1988; 177 SABESAN, S (WOS:A1986A932500056) 1986; 108 Hada, N (WOS:000378974500028) 2016; 64 Friedl, CH (WOS:000180871000011) 2003; 369 Koizumi, A (WOS:000289655100035) 2011; 46 Koizumi, A (WOS:000308211100026) 2012; 17 |
| References_xml | – reference: 10) Koizumi A., Hada N., Kaburaki A., Yamano K., Schweizer F., Takeda T., Carbohydr. Res., 344, 856–868 (2009). – reference: 16) Nakamura-Uchiyama F., Tokunaga Y., Suzuki A., Akao N., Hiromatsu K., Hitomi S., Nawa Y., Scand. J. Infect. Dis., 38, 221–224 (2006). – reference: 23) Veeneman G. H., van Leeuwen S. H., van Boom J. H., Tetrahedron Lett., 31, 1331–1334 (1990). – reference: 21) Xia J., Alderfer J. L., Locke R. D., Piskorz C. F., Matta K. L., J. Org. Chem., 68, 2752–2759 (2003). – reference: 24) Scaman C. H., Hindsgaul O., Palcic M. M., Srivastava O. P., Carbohydr. Res., 296, 203–213 (1996). – reference: 17) Friedl C. H., Lochnit G., Zahringer U., Bahr U., Geyer R., Biochem. J., 369, 89–102 (2003). – reference: 6) Ozawa H., Sonoda Y., Kato S., Suzuki E., Matsuoka R., Kanaya T., Kiuchi F., Hada N., Kasahara T., Biol. Pharm. Bull., 35, 2054–2058 (2012). – reference: 8) Koizumi A., Yamano K., Tsuchiya T., Schweizer F., Kiuchi F., Hada N., Molecules, 17, 9023–9042 (2012). – reference: 20) Schmidt R. R., Angew. Chem. Int. Ed. Engl., 25, 212–235 (1986). – reference: 13) Ohtsuka I., Hada N., Ohtaka H., Sugita M., Takeda T., Chem. Pharm. Bull., 50, 600–604 (2002). – reference: 25) Dasgupta F., Garegg P. J., Carbohydr. Res., 177, c13–c17 (1988). – reference: 18) Sarkar S. K., Roy N., J. Carbohydr. Chem., 22, 285–296 (2003). – reference: 22) Hada N., Oka J., Nishiyama A., Takeda T., Tetrahedron Lett., 47, 6647–6650 (2006). – reference: 5) Ohtsuka I., Hada N., Atsumi T., Kakiuchi N., Tetrahedron, 69, 1470–1475 (2013). – reference: 26) Grundler G., Schmidt R. R., Carbohydr. Res., 135, 203–218 (1985). – reference: 11) Lochnit G., Dennis R. D., Ulmer A. J., Geyer R., J. Biol. Chem., 273, 466–474 (1998). – reference: 14) Yamano K., Koizumi A., Takeda T., Kiuchi F., Hada N., Parasitol. 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| SubjectTerms | Ascaris suum Biotin biotin probe Chemistry Chemistry, Medicinal Chemistry, Multidisciplinary glycosphingolipid Glycosphingolipids host–parasite interaction Life Sciences & Biomedicine Oligosaccharides Pharmacology & Pharmacy Physical Sciences Science & Technology stereocontrolled synthesis Synthesis |
| Title | Synthesis of the Non Reducing End Oligosaccharides of Glycosphingolipids from Ascaris suum |
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