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ID 16056
Eprint ID
16056
FullText URL
99_1529.pdf 684 KB
Title Alternative
Synthesis and incorporation into the brain of di-4-amino-3(RS)-hydroxybutanoic acid maleate
Author
Miyamoto, Shigetoshi
Abstract
Resolution of 4-amino-3-hydroxybutanamide and 4-amino-3-hydroxybutananilide was carried out with optically active camphor-l0-sulfonic acid and tartaric acid, respectively. Hydrolysis of optically active 4-amino-3-hydroxybutanamide and 4-amino-3-hydroxybutananilide on a strongly acidic resin yielded 4-amino-3(R)-hydroxybutanoic acid (R-GABOB) and 4-amino-3(S)-hydroxybutanoic acid (S-GABOB). As Infrared absorption spectrums of R-GABOB and 4-amino-3(RS)-hydroxybutanoic acid (RS-GABOB) were different, RS-GABOB was shown to be a racemic compound. Although direct resolution of a racemic compound is impossible, RS-GABOB was converted into a racemic mixture as the corresponding salt of mxylenesulfonic acid, and resolution was accomplished by selective crystallization. RS-GABOB is a racemic compound, its incorporation into the brain is a little. It is known that incorpration into the brain of optically active R-GABOB is greater than that of RS-GABOB or optically active S-GABOB. We discovered that the incorporation into the brain of di-RS-GABOB-maleate-1-(14)C, upon i.p. injection was greater than that of RS-GABOB-1-(14)C. As di-RS-GABOB-maleate has the monomolecular action of RS-GABOB in circulative blood, it passes easily through the blood brain barrier.
Keywords
RS-GABOB
di-RS-GABOB-maleate
血液脳関門
Published Date
1987-12-30
Publication Title
岡山医学会雑誌
Publication Title Alternative
Journal of Okayama Medical Association
Volume
volume99
Issue
issue11-12
Publisher
岡山医学会
Publisher Alternative
Okayama Medical Association
Start Page
1529
End Page
1537
ISSN
0030-1558
NCID
AN00032489
Content Type
Journal Article
Official Url
https://www.jstage.jst.go.jp/article/joma1947/99/11-12/99_11-12_1529/_article/-char/ja/
Related Url
http://www.okayama-u.ac.jp/user/oma/index.html
language
日本語
Copyright Holders
岡山医学会
File Version
publisher
Refereed
True
Eprints Journal Name
joma