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

Y. Murakami, Yoshio Hisaeda, T. Ohno

Research output: Contribution to journalArticle

54 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

Fingerprint

Alkylation
Vitamin B 12
Cobalt
Bromides
Derivatives
Methanol
Solubility
Lipids
cetrimonium

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{17dd1de53d194a5b80d6df5f3e7422a9,
title = "Hydrophobic vitamin B12. III. Incorporation of hydrophobic vitamin B12 derivatives into single-compartment vesicles and their alkylation in various molecular aggregates",
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.",
author = "Y. Murakami and Yoshio Hisaeda and T. Ohno",
year = "1984",
doi = "10.1246/bcsj.57.2091",
language = "English",
volume = "57",
pages = "2091--2097",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "The Chemical Society of Japan",
number = "8",

}

TY - JOUR

T1 - Hydrophobic vitamin B12. III. Incorporation of hydrophobic vitamin B12 derivatives into single-compartment vesicles and their alkylation in various molecular aggregates

AU - Murakami, Y.

AU - Hisaeda, Yoshio

AU - Ohno, T.

PY - 1984

Y1 - 1984

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0021232003&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0021232003&partnerID=8YFLogxK

U2 - 10.1246/bcsj.57.2091

DO - 10.1246/bcsj.57.2091

M3 - Article

VL - 57

SP - 2091

EP - 2097

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 8

ER -