Hydrophobic vitamin B12. III. Incorporation of hydrophobic vitamin B12 derivatives into single-compartment vesicles and their alkylation in various molecular aggregates.
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概要
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The incorporation of hydrophobic vitamin B<SUB>12</SUB> derivatives into the single-compartment vesicles of <I>N</I>,<I>N</I>-didodecyl-<I>N</I><SUP>α</SUP>-[6-(tyimethylammonio)hexanoyl]-L-alaninamide bromide (N<SUP>+</SUP>C<SUB>5</SUB>Ala2C<SUB>12</SUB>) was found to be primarily concerned with the extent of insolubility of the cobalt complexes in the aqueous bulk phase, while such incorporation into the single-walled vesicles of <I>N</I>,<I>N</I>-ditetradecyl-<I>N</I><SUP>α</SUP>-[6-(trimethylammonio)hexanoyl]-L-histidinamide bromide (N<SUP>+</SUP>C<SUB>5</SUB>His2C<SUB>14</SUB>) was enhanced by the coordination interaction between the cobalt complex and the imidazolyl group of the lipid. In molecular aggregates formed with hexadecyltrimethylammonium bromide, α-[4-(1,1,3,3-tetramethylbutyl)phenyl]-ω-hydroxypoly(oxyethylene), or N<SUP>+</SUP>C<SUB>5</SUB>Ala2C<SUB>12</SUB>, the alkylation rates of a hydrophobic vitamin B<SUB>12</SUB> with 1-bromo-2-methylpropane and methyl 2-methyl-3-bromopropanoate were much enhanced relative to those in methanol. In the N<SUP>+</SUP>C<SUB>5</SUB>Ala2C<SUB>12</SUB> vesicle, a two-step mechanism was observed for the alkylation with the latter reagent. The possible origin of such rate enhancement was discussed.
- 公益社団法人 日本化学会の論文
著者
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Hisaeda Yoshio
Department Of Applied Chemistry Graduate School Of Engineering Kyushu University
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Murakami Yukito
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
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Ohno Teruhisa
Department Of Applied Chemistry Faculty Of Engineering Kyushu Institute Of Technology
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