Enzymatic Polymerization of Activated Glycosyl Monomers for Highly Selective Polysaccharide Synthesis

Shoda SI; Okamoto E; Fujita M; Osada S; Ito K; Abidin ZZ; Kobayashi S

Korea Polymer Journal, Vol.4, No.2, 112-116, October, 1996

Shoda SI, Okamoto E, Fujita M, Osada S, Ito K, Abidin ZZ, Kobayashi S

Highly regio-and strereoselective enzymatic polymerizations for the synthesis of oligo-and polysaccharides have been developed by using various glycosyl fluorides and a glycosyl phosphate as activated glycosyl monomers for enzymatic polymerization. The resulting polymers are nonnatural oligo-and polysaccharides which are difficult to prepare by the conventional chemical methods with use of protecting groups.

[References]

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Kobayashi S, Kashiwa K, Kawasaki T, Shoda S, J. Am. Chem. Soc., 113, 3079 (1991)
Osada S, Okamoto E, Ito K, Shoda S, Kobayashi S, 69th Annu. Meet. Chem. Soc., Jpn. Prepr., II, 682 (1995)
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Shoda S, Okamoto E, Kiyusada T, Kobayashi S, Macromol. Rapid Commun., 15, 751 (1994)
Shoda S, Okamoto E, Kiyosada T, Kobayashi S, Proc. 1st Annu. Meet. Cellulose Soc. Jpn., 77 (1994)
Kiyosada T, Shoda S, Kobayashi S, Polym. Prepr., 42, 2166 (1993)
Okamoto E, Shoda S, Kobayashi S, Polym. Prepr., 42, 2169 (1993)
Fujita M, Shoda S, Kobayashi S, Polym. Prepr., 45, 589 (1996)
Ziegast G, Pfannemuller G, Carbohydr. Res., 18, 160 (1987)

[1] Preston RD, The Physical Biology of Plant Cell Walls, Chapman and Hall, London (1974)

[2] Wilkie KCB, Adv. Carbohydr. Chem. Biochem., 36, 215 (1979)

[3] French D, Biochemistry of Carbohydrates, MTP Intern. Rev. Sci., Biochem. Ser. 1, W.J. Whelan, Ed., Butterworths, University Park Press, London and Baltimore, Vol. 5, pp. 267 (1975)

[4] Banks W, Muri DD, Biochemistry of Plants, Carbohydrates: Structure and Function, J. Preiss, Ed., Academic Press, New York, Vol. 3 (1980)

[5] Lasky LA, Science, 258, 964 (1992)

[6] Varki A, Glycobiology, 3, 97 (1993)

[7] Kannagi R, Hakomori S, Handbook of Experimental Immunology, Applications of immunological Methods in Biomecial Science, Weir and Herzenberg Eds., Blackwell Scientific Pub. Inc., Boston, U.S.A., Vol. 4, pp. 117.1-117.20 (1986)

[8] Shoda S, Kobayashi S, Trends Polym. Sci., submitted

[9] Khan SH, O'Neill RA, Modern Methods in Carbohydrate Synthesis, Harwood Academic Pub., Amsterdam (1996)

[10] Nilsson KGI, Trends Biotechnol., 6, 256 (1988)

[11] Wong CH, Halcomb RL, Ichikawa Y, Kajimoto T, Angew. Chem.-Int. Edit., 34, 521 (1995)

[12] Barnett JEG, Jarvis WTS, Munday KA, Biochem. J., 105, 669 (1967)

[13] Kobayashi S, Kashiwa K, Kawasaki T, Shoda S, J. Am. Chem. Soc., 113, 3079 (1991)

[14] Osada S, Okamoto E, Ito K, Shoda S, Kobayashi S, 69th Annu. Meet. Chem. Soc., Jpn. Prepr., II, 682 (1995)

[15] Methods in Carbohydrate Chemistry, R.L. Whistler, Ed., Academic Press, New York, Vol. III (1963)

[16] Shoda S, Okamoto E, Kiyusada T, Kobayashi S, Macromol. Rapid Commun., 15, 751 (1994)

[17] Shoda S, Okamoto E, Kiyosada T, Kobayashi S, Proc. 1st Annu. Meet. Cellulose Soc. Jpn., 77 (1994)

[18] Kiyosada T, Shoda S, Kobayashi S, Polym. Prepr., 42, 2166 (1993)

[19] Okamoto E, Shoda S, Kobayashi S, Polym. Prepr., 42, 2169 (1993)

[20] Fujita M, Shoda S, Kobayashi S, Polym. Prepr., 45, 589 (1996)

[21] Ziegast G, Pfannemuller G, Carbohydr. Res., 18, 160 (1987)