Hydrophobic vitamin B12. III. Incorporation of hydrophobic vitamin B12 derivatives into single-compartment vesicles and their alkylation in various molecular aggregates

Y. Murakami, Y. Hisaeda, T. Ohno

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53 Citations (Scopus)

Abstract

The incorporation of hydrophobic vitamin B12 derivatives into the single-compartment vesicles of N'N,-didodecyl-N(α)-[6-(tyimethylammonio)hexanoyl]-L-alaninamide bromide (N+C5Ala2C12) 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 N,N-ditetradecyl-N(α)-[6-(trimethylammonio)hexanoyl]-L-histidinamide bromide (N+C5His2C14) 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+C5Ala2C12, the alkylation rates of a hydrophobic vitamin B12 with 1-bromo-2-methylpropane and methyl 2-methyl-3-bromopropanoate were much enhanced relative to those in methanol. In the N+C5Ala2C12 vesicle, a two-step mechanism was observed for the alkylation with the latter reagent. The possible origin of such rate enhancement was discussed.

Original languageEnglish
Pages (from-to)2091-2097
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume57
Issue number8
DOIs
Publication statusPublished - 1984

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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