Synthesis of New Spherical Polylysine Oligosaccharide Dendrimers with C6 Methylene Spacer

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  • Ying Li
    Department of Bio and Environmental Chemistry, Kitami Institute of Technology
  • Shuqin Han
    Department of Bio and Environmental Chemistry, Kitami Institute of Technology
  • Uryu Toshiyuki
    Department of Bio and Environmental Chemistry, Kitami Institute of Technology
  • Yoshida Takashi
    Department of Bio and Environmental Chemistry, Kitami Institute of Technology Research Center for Environmentally Friendly Materials Engineering, Muroran Institute of Technology

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New first, second, and third generation sphere-type polylysine glycodendrimers with cellobiose units at the terminal (first, second, and third generation cellobiose-C6 spacer-polylysine dendrimers) were synthesized from 1, 4-diaminobutane as a starting compound. Repeated condensations by N, N- bis(tert-butoxycarbonyl)-L-lysine (di-boc-lysine) and deprotections of the boc groups gave the first, second, and third generation sphere-type polylysine dendrimers with 4, 8, and 16 amino groups at the terminal in 75%, 82%, and 83% yields, respectively. To increase the flexibility of attached oligosaccharides at the terminal, a methylene spacer with six methylene carbons (C6 methylene spacer) was introduced between the polylysine dendrimers and cellobiose; that is, ethyl 1-hydroxylhexanoate was reacted with peracetylated α-D-cellobiosyl bromide to afford 2, 2', 3, 3', 4', 6, 6'-hepta-O-acetyl-1-O-(6- ethoxycarbonylpentoxy)-β-D-cellobioside. After hydrolysis of the acetyl and ethyl ester groups to recover hydroxyl groups and carboxylic acid, the obtained cellobiose unit with a carboxylic acid at the end of the C6 methylene spacer was condensed with the terminal amino groups of the polylysine dendrimers to give first, second, and third generation sphere-type cellobiose-C6 spacer-polylysine dendrimers in 48%, 53%, and 55% yields, respectively. The cellobiose unit was connected by the peptide bond to the polylysine dendrimers through the C6 methylene spacer without decomposition of the cellulobiose structure. MALDI TOF MS measurements gave signals that decreased at regular intervals because the molecular weight of the cellobiose unit was around 444 Da and it was found that the average substitution of the cellobiose unit gave nearly 4 among 4, 6.8 among 8, and 11 units among 16 terminal amino groups in the first, second, and third generation polylysine dendrimers, respectively, on high resolution 1H NMR and MALDI TOF MS spectra.

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  • 繊維学会誌

    繊維学会誌 71 (1), 10-17, 2015

    社団法人 繊維学会

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