메뉴 건너뛰기




Volumn 32, Issue 4, 2013, Pages 240-248

Synthesis of 5-Thio-D-galactopyranose

Author keywords

5 Thio D galactopyranose; Galactofuranose; Glycosidase inhibitors; Thiirane; Thiosugars

Indexed keywords


EID: 84880202712     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328303.2013.800086     Document Type: Article
Times cited : (5)

References (22)
  • 1
    • 79952438320 scopus 로고    scopus 로고
    • Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent-glucosidase inhibitors
    • Xie, W.; Tanabe, G.; Akaki, J.; Morikawa, T.; Ninomiya, K.; Minematsu, T.; Yoshikawa, M.; Wu, X.; Muraoka, O. Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent-glucosidase inhibitors. Bioorg. Med. Chem. 2011, 19, 2015-2022.
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 2015-2022
    • Xie, W.1    Tanabe, G.2    Akaki, J.3    Morikawa, T.4    Ninomiya, K.5    Minematsu, T.6    Yoshikawa, M.7    Wu, X.8    Muraoka, O.9
  • 2
    • 0036185571 scopus 로고    scopus 로고
    • Absolute stereostructure of potent α-glucosidase inhibitor, salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata
    • DOI 10.1016/S0968-0896(01)00422-9, PII S0968089601004229
    • Yoshikawa, M.; Morikawa, T.; Matsuda, H.; Tanabe, G.; Muraoka, O. Absolute stereostructure of potent-glucosidase inhibitor, salacinol, with unique thiosugar sulfonium sulfate inner salt structure from salacia reticulate. Bioorg. Med. Chem. 2002, 10, 1547-1554. (Pubitemid 34214717)
    • (2002) Bioorganic and Medicinal Chemistry , vol.10 , Issue.5 , pp. 1547-1554
    • Yoshikawa, M.1    Morikawa, T.2    Matsuda, H.3    Tanabe, G.4    Muraoka, O.5
  • 4
    • 29544447220 scopus 로고    scopus 로고
    • Thiosugars: New perspectives regarding availability and potential biochemical and medicinal applications
    • DOI 10.1007/s00253-005-0156-x
    • Witczak, Z.J.; Culhane, J.M. Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications. Appl. Microbiol. Biotechnol. 2005, 69, 237-244. (Pubitemid 43014440)
    • (2005) Applied Microbiology and Biotechnology , vol.69 , Issue.3 , pp. 237-244
    • Witczak, Z.J.1    Culhane, J.M.2
  • 5
    • 0036664538 scopus 로고    scopus 로고
    • Antidiabetogenic constituents from several natural medicines
    • Matsuda, H.; Morikawa, T.; Yoshikawa, M. Antidiabetogenic constituents from several natural medicines. Pure Appl. Chem. 2002, 74, 1301-1308.
    • (2002) Pure Appl. Chem , vol.74 , pp. 1301-1308
    • Matsuda, H.1    Morikawa, T.2    Yoshikawa, M.3
  • 6
    • 0032546507 scopus 로고    scopus 로고
    • Syntheses of 1-deoxy-3-S-(1-thio-α-D-glucopyranosyl)-mannojirimycin and 1-deoxy-3-O-(5-thio-α-D-glucopyranosyl)-mannojirimycin as potential inhibitors of endo-α-D-mannosidase
    • DOI 10.1016/S0960-894X(98)00198-X, PII S0960894X9800198X
    • Ding, Y.; Hindsgaul, O. Syntheses of 1-deoxy-3-S-(1-thio-?-D-gluco- pyranosyl)-mannojirimycin and 1-deoxy-3-O-(5-thio-?-D-glucopyranosyl)-manno jirimycin as potential inhibitors of endo-?-D-mannosidase. Bioorg. Med. Chem. Lett. 1998, 8, 1215-1220. (Pubitemid 28231401)
    • (1998) Bioorganic and Medicinal Chemistry Letters , vol.8 , Issue.10 , pp. 1215-1220
    • Ding, Y.1    Hindsgaul, O.2
  • 7
    • 0025167326 scopus 로고
    • Synthesis of 5-thio-L-fucose and its inhibitory effect on fucosidase
    • Hashimoto, H.; Fujimori, T.; Yuasa, H. Synthesis of 5-thio-L-fucose and its inhibitory effect on fucosidase. J. Carbohydr. Chem. 1990, 280, 683-694. (Pubitemid 20334302)
    • (1990) Journal of Carbohydrate Chemistry , vol.9 , Issue.5 , pp. 683-694
    • Hashimoto, H.1    Fujimori, T.2    Yuasa, H.3
  • 8
    • 37049044350 scopus 로고
    • D-Xylothiapyranose a sugar with sulphur in the ring
    • Schwarz, J.C.P.; Yule, K.C. D-Xylothiapyranose: a sugar with sulphur in the ring. Proc. Chem. Soc. 1961, 417-417.
    • (1961) Proc. Chem. Soc , pp. 417-417
    • Schwarz, J.C.P.1    Yule, K.C.2
  • 9
    • 0001273098 scopus 로고
    • Introduction of a new hetero atom into a sugar ring
    • Whistler, R.L.; Feather, M.S.; Ingles, D.L. Introduction of a new hetero atom into a sugar ring. J. Am. Chem. Soc. 1962, 84, 122-122.
    • (1962) J. Am. Chem. Soc , vol.84 , pp. 122-122
    • Whistler, R.L.1    Feather, M.S.2    Ingles, D.L.3
  • 10
    • 0015560085 scopus 로고
    • The pancreatic-cell recognition of insulin secretagogues III: Effects of substituting sulphur for oxygen in the D-glucose molecule
    • Hellman, B.; Lernmark, A.; Sehlin, J.; Taljedal, J.B.; Whistler, R.L. The pancreatic ?-cell recognition of insulin secretagogues III: effects of substituting sulphur for oxygen in the D-glucose molecule. Biochem. Pharmacol. 1973, 22, 29-35.
    • (1973) Biochem. Pharmacol , vol.22 , pp. 29-35
    • Hellman, B.1    Lernmark, A.2    Sehlin, J.3    Taljedal, J.B.4    Whistler, R.L.5
  • 11
    • 0015446464 scopus 로고
    • Inhibition of cellular transport processes by 5-thio-Dglucopyranose
    • Whistler, R.L.; Lake, W.C. Inhibition of cellular transport processes by 5-thio-Dglucopyranose. Biochem. J. 1972, 130, 919-925.
    • (1972) Biochem. J , vol.130 , pp. 919-925
    • Whistler, R.L.1    Lake, W.C.2
  • 13
    • 2042546805 scopus 로고
    • 5-Thio-D-mannose from marine sponge Clathria pyramida (Lendenfeld). The first example of a naturally occurring 5-thiosugar
    • Capon, R.J.; MacLeod, J.K. 5-Thio-D-mannose from marine sponge Clathria pyramida (Lendenfeld). The first example of a naturally occurring 5-thiosugar. J. Chem. Soc. Chem. Commun. 1987, 15, 1200-1201.
    • (1987) J. Chem. Soc. Chem. Commun , vol.15 , pp. 1200-1201
    • Capon, R.J.1    MacLeod, J.K.2
  • 14
    • 0035712771 scopus 로고    scopus 로고
    • Synthesis and biological properties of monothiosaccharides
    • DOI 10.2174/1385272013374743
    • Robina, I.; Vogel, P.; Witczak, Z.J. Synthesis and biological properties of monothiosaccharides. Curr. Org. Chem. 2001, 5, 1177-1214. (Pubitemid 34149837)
    • (2001) Current Organic Chemistry , vol.5 , Issue.12 , pp. 1177-1214
    • Robina, I.1    Vogel, P.2    Witczak, Z.J.3
  • 15
    • 0034733902 scopus 로고    scopus 로고
    • Synthesis of 5-thio-L-altrose
    • DOI 10.1016/S0008-6215(00)00052-5, PII S0008621500000525
    • Hughes, N.A. Synthesis of 5-thio-L-altrose. Carbohydr. Res. 2000, 326, 323-325. (Pubitemid 30386919)
    • (2000) Carbohydrate Research , vol.326 , Issue.4 , pp. 323-325
    • Hughes, N.A.1
  • 17
    • 0029866313 scopus 로고    scopus 로고
    • Novel conversion of aldopyranosides into 5-thioaldopyranosides via acyclic monothioacetals with inversion and retention of configuration at C-5
    • DOI 10.1016/0008-6215(95)00386-X
    • Hashimoto, H.; Kawanishi, M.; Yuasa, H. Novel conversion of aldopyranosides into 5-thioaldopyranosides via acyclic monothioacetals with inversion and retention of configuration at C-5. Carbohydr. Res. 1996, 282, 207-221. (Pubitemid 26086319)
    • (1996) Carbohydrate Research , vol.282 , Issue.2 , pp. 207-221
    • Hashimoto, H.1    Kawanishi, M.2    Yuasa, H.3
  • 18
    • 0002463469 scopus 로고
    • Synthesis of 5-thio-D-glucose
    • Nayak, U.G.; Whistler, R.L. Synthesis of 5-thio-D-glucose. J. Org. Chem. 1969, 34, 97-100.
    • (1969) J. Org. Chem , vol.34 , pp. 97-100
    • Nayak, U.G.1    Whistler, R.L.2
  • 19
    • 0000933381 scopus 로고
    • Synthesis of 5-thio-D-galactose
    • Shin, J.E.N.; Perlin, A.S. Synthesis of 5-thio-D-galactose. Carbohydr. Res. 1979, 76, 165-176.
    • (1979) Carbohydr. Res , vol.76 , pp. 165-176
    • Shin, J.E.N.1    Perlin, A.S.2
  • 20
    • 0030847463 scopus 로고    scopus 로고
    • UDP-N-acetyl-5-thiogalactosamine is a substrate of lactose synthase
    • Tsuruta, O.; Shinohara, G.; Yuasa, H.; Hashimoto, H. UDP-N-acetyl-5- thiogalactosamine is a substrate of lactose synthase. Bioorg. Med. Chem. Lett. 1997, 7, 2523-2526.
    • (1997) Bioorg. Med. Chem. Lett , vol.7 , pp. 2523-2526
    • Tsuruta, O.1    Shinohara, G.2    Yuasa, H.3    Hashimoto, H.4
  • 21
    • 84855556135 scopus 로고    scopus 로고
    • Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes
    • Repetto, E.; Manzano, V.E.; Uhrig, M.L.; Varela, O. Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes. J. Org. Chem. 2012, 77, 253-265.
    • (2012) J. Org. Chem , vol.77 , pp. 253-265
    • Repetto, E.1    Manzano, V.E.2    Uhrig, M.L.3    Varela, O.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.