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Volumn 62, Issue 9, 1997, Pages 2832-2846

Synthesis of kojidextrins and their protein conjugates. Incidence of steric mismatch in oligosaccharide synthesis

Author keywords

[No Author keywords available]

Indexed keywords

DEXTRIN; OLIGOSACCHARIDE;

EID: 0030996192     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962300y     Document Type: Article
Times cited : (48)

References (65)
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    • Kojibiose: (a) Matsuda, K. Nature 1957, 985. (b) Helferich, B.; Zirner, J. Chem. Ber. 1962, 95, 2604-2611. (c) Wolfrom, M. L.; Thompson, A.; Lineback, D. R. J. Org. Chem. 1963, 28, 860-861. (d) Igarashi, K.; Irisawa, J.; Honma, T. Carbohydr. Res. 1975, 39, 341-343. (e) Aspinall, G. O.; Gurjar, M. K. Carbohydr. Res. 1985, 143, 266-270. (f) Nepogodev, S. A.; Backinowsky, L. V.; Grzeszczyk, B.; Zamojski, A. Carbohydr. Res. 1994, 254, 43-60. (g) Pozsgay, V.; Robbins, J. B. Carbohydr. Res. 1995, 277, 51-66. (h) Dubois, E. P.; Robbins, J. B.; Pozsgay, V. Bioorg. Med. Chem. Lett. 1996, 6, 1387-1392.
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    • Pozsgay, V.1    Robbins, J.B.2
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    • Kojibiose: (a) Matsuda, K. Nature 1957, 985. (b) Helferich, B.; Zirner, J. Chem. Ber. 1962, 95, 2604-2611. (c) Wolfrom, M. L.; Thompson, A.; Lineback, D. R. J. Org. Chem. 1963, 28, 860-861. (d) Igarashi, K.; Irisawa, J.; Honma, T. Carbohydr. Res. 1975, 39, 341-343. (e) Aspinall, G. O.; Gurjar, M. K. Carbohydr. Res. 1985, 143, 266-270. (f) Nepogodev, S. A.; Backinowsky, L. V.; Grzeszczyk, B.; Zamojski, A. Carbohydr. Res. 1994, 254, 43-60. (g) Pozsgay, V.; Robbins, J. B. Carbohydr. Res. 1995, 277, 51-66. (h) Dubois, E. P.; Robbins, J. B.; Pozsgay, V. Bioorg. Med. Chem. Lett. 1996, 6, 1387-1392.
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    • Kojitriose: (a) Takeo, K. Carbohydr. Res. 1981, 88, 158-161. (b) Takeo, K.; Suzuki, Y. Carbohydr. Res. 1987, 162, 95-109. (c) Ref. 10g. (d) Reference 10h.
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    • Kojitriose: (a) Takeo, K. Carbohydr. Res. 1981, 88, 158-161. (b) Takeo, K.; Suzuki, Y. Carbohydr. Res. 1987, 162, 95-109. (c) Ref. 10g. (d) Reference 10h.
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    • Kojitriose: (a) Takeo, K. Carbohydr. Res. 1981, 88, 158-161. (b) Takeo, K.; Suzuki, Y. Carbohydr. Res. 1987, 162, 95-109. (c) Ref. 10g. (d) Reference 10h.
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    • Kojitetraose and kojipentaose: (a) Reference 10g. (b) Reference 10h. (c) Reference 12b
    • Kojitetraose and kojipentaose: (a) Reference 10g. (b) Reference 10h. (c) Reference 12b.
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    • Ref 10e
    • (c) Ref 10e.
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    • 12b used methyl 2-O-allyl-4,6-O- benzylidene-α-D-glucopyranoside as the precursor, which was prepared by several groups [(a) Küster, J. M.; Dyong, I. Liebigs Ann. Chem. 1975, 2179-2189. (b) Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1994, 265, 145-149. (c) Dasgupta, F.; Garegg, P. J. Synthesis 1994, 1121- 1123] by regioselective monoallylation of methyl 4,6-O-benzylidene- α-D-glucopyranoside. Careful reproduction of these protocols gave mixtures of the 2-O- and 3-O-allyl derivatives from which the isolation of the 2-O-allyl derivative proved to be impractical.
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    • 12b used methyl 2-O-allyl-4,6-O- benzylidene-α-D-glucopyranoside as the precursor, which was prepared by several groups [(a) Küster, J. M.; Dyong, I. Liebigs Ann. Chem. 1975, 2179-2189. (b) Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1994, 265, 145-149. (c) Dasgupta, F.; Garegg, P. J. Synthesis 1994, 1121- 1123] by regioselective monoallylation of methyl 4,6-O-benzylidene- α-D-glucopyranoside. Careful reproduction of these protocols gave mixtures of the 2-O- and 3-O-allyl derivatives from which the isolation of the 2-O-allyl derivative proved to be impractical.
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    • 12b used methyl 2-O-allyl-4,6-O- benzylidene-α-D-glucopyranoside as the precursor, which was prepared by several groups [(a) Küster, J. M.; Dyong, I. Liebigs Ann. Chem. 1975, 2179-2189. (b) Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1994, 265, 145-149. (c) Dasgupta, F.; Garegg, P. J. Synthesis 1994, 1121- 1123] by regioselective monoallylation of methyl 4,6-O-benzylidene- α-D-glucopyranoside. Careful reproduction of these protocols gave mixtures of the 2-O- and 3-O-allyl derivatives from which the isolation of the 2-O-allyl derivative proved to be impractical.
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    • α,α-Dichloromethyl methyl ether (DCMME) has been used extensively for the introduction of chlorine to the anomeric center in methyl glycosides and glycosyl acetates, see, e.g.: Pozsgay, V.; Coxon, B.; Yeh, H. Bioorg. Med. Chem. 1993, 1, 237-257. For the only reported use of DCMME for the conversion of thioglycosides to glycosyl chlorides, see: Farkas, I.; Bognár, R.; Menyhárt, M. M.; Tarnai, A. K.; Bihari, M.; Tamás, J. Acta Chim. 1975, 84, 325-334.
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    • Pozsgay, V.1    Coxon, B.2    Yeh, H.3
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    • α,α-Dichloromethyl methyl ether (DCMME) has been used extensively for the introduction of chlorine to the anomeric center in methyl glycosides and glycosyl acetates, see, e.g.: Pozsgay, V.; Coxon, B.; Yeh, H. Bioorg. Med. Chem. 1993, 1, 237-257. For the only reported use of DCMME for the conversion of thioglycosides to glycosyl chlorides, see: Farkas, I.; Bognár, R.; Menyhárt, M. M.; Tarnai, A. K.; Bihari, M.; Tamás, J. Acta Chim. 1975, 84, 325-334.
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    • For an excellent review on the use of DCMME for the conversion of glycosyl acetates and O- and S-glycosides into glycosyl chlorides, see: Gross, H. Z. Chem. 1978, 18, 201-210.
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    • For related observations, see: (a) Szurmai, Z.; Lipták, A. Carbohydr. Res. 1982, 107, 33-41. (b) Szurmai, Z.; Lipták, A.; Schnatzke, G. Carbohydr. Res. 1990, 200, 201-208. (c) Borbás, A; Lipták, A. Carbohydr. Res. 1993, 241, 99-116.
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    • For related observations, see: (a) Szurmai, Z.; Lipták, A. Carbohydr. Res. 1982, 107, 33-41. (b) Szurmai, Z.; Lipták, A.; Schnatzke, G. Carbohydr. Res. 1990, 200, 201-208. (c) Borbás, A; Lipták, A. Carbohydr. Res. 1993, 241, 99-116.
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    • For related observations, see: (a) Szurmai, Z.; Lipták, A. Carbohydr. Res. 1982, 107, 33-41. (b) Szurmai, Z.; Lipták, A.; Schnatzke, G. Carbohydr. Res. 1990, 200, 201-208. (c) Borbás, A; Lipták, A. Carbohydr. Res. 1993, 241, 99-116.
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    • Borbás, A.1    Lipták, A.2
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    • For an excellent review on the use of 2-(trimethylsilyl)ethyl glycosides in oligosaccharide synthesis, see: Magnusson, G. Trends Glycosci. Glycotechnol. 1992, 4, 358-367.
    • (1992) Trends Glycosci. Glycotechnol. , vol.4 , pp. 358-367
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