Synthesis of sugar amino acids via base hydrolysis of sugar aminonitriles
Other Title(s)
تحضير أحماض أمينية سكرية عن طريق التحلل المائي القاعدي لنتريلات السكر الأمينية
Dissertant
Thesis advisor
al-Araji, Suad Mustafa
al-Fattahi, Yusuf Ali
Comitee Members
al-Rafiq, Ilham M.
al-Azzawi, Ahlam Maruf
al-Qazzaz, Fatin Fadil
University
University of Baghdad
Faculty
College of Science
Department
Chemistry Department
University Country
Iraq
Degree
Master
Degree Date
2007
English Abstract
This work includes synthesis of new N-substituted sugar-a-amino acids, so that one of the monosaccharide carbon atoms represents the a- position of the a-amino acid.
In order to obtain these derivatives; the known 2,3:4,5-di-Oisopropylidene- b-D-fructopyranose (89) and 1,2:3,4-di-O-isopropylidene- a-D-galactopyranose (91) were prepared from D-fructose and Dgalactose, respectively and used as starting materials.
The oxidation of the primary alcohol (89) by using dimethyl sulfoxide/acetic anhydride, pyridinium chlorochromate or pyridinium dichromate/acetic anhydride afforded the corresponding aldehyde (90), but the latter method had the priority over the other two methods for the oxidation of (89) and also for the oxidation of the alcohol (91) to the corresponding aldehyde (92).
Compounds (90) and (92) were subjected to a modified Streckertype reaction, whereby different primary aliphatic amines in common with the cyanide ion were introduced successfully, and new a- aminonitriles (93-98) were thus obtained in good yield.
Thin-layer chromatography of the prepared a-aminonitriles, indicated that each derivative may exist in a mixture of two stereoisomers with different proportions.
Base hydrolysis of the sugar-a-aminonitriles (93-98) by using (35%) aqueous sodium hydroxide solution, at reflux temperature gave the desired sugar-a-amino acids (99-104).
FTIR spectroscopy was utilized for the characterization of the synthesized compounds.
Main Subjects
No. of Pages
95
Table of Contents
Table of contents.
Abstract.
Abstract in Arabic.
Chapter One : Introduction.
Chapter Two : Experimental.
Chapter Three : Results and discussion.
References.
American Psychological Association (APA)
Muhammad, Umar Abd al-Latif. (2007). Synthesis of sugar amino acids via base hydrolysis of sugar aminonitriles. (Master's theses Theses and Dissertations Master). University of Baghdad, Iraq
https://search.emarefa.net/detail/BIM-599321
Modern Language Association (MLA)
Muhammad, Umar Abd al-Latif. Synthesis of sugar amino acids via base hydrolysis of sugar aminonitriles. (Master's theses Theses and Dissertations Master). University of Baghdad. (2007).
https://search.emarefa.net/detail/BIM-599321
American Medical Association (AMA)
Muhammad, Umar Abd al-Latif. (2007). Synthesis of sugar amino acids via base hydrolysis of sugar aminonitriles. (Master's theses Theses and Dissertations Master). University of Baghdad, Iraq
https://search.emarefa.net/detail/BIM-599321
Language
English
Data Type
Arab Theses
Record ID
BIM-599321
