Item – Theses Canada

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OCLC number
72981986
Link(s) to full text
LAC copy
LAC copy
Author
Connolly, Lori C.(Lori Colleen),1981-
Title
The stereoselective synthesis of nitrile amino acids using a chiral Schiff base complex.
Degree
M. Sc. -- Dalhousie University, 2005
Publisher
Ottawa : Library and Archives Canada = Bibliothèque et Archives Canada, [2005]
Description
2 microfiches
Notes
Includes bibliographical references.
Abstract
This thesis focuses on the synthesis of ('S')- and (' R')-Schiff base complexes of Ni2+, glycine, and 2-[' N'-('N''-benzylprolyl)amino]benzophenone (BPB) and their use in the stereoselective synthesis of a series of nitrile amino acids, a class of non-protein amino acids. Optimized reaction conditions are presented for the alkylation of ('S')- and ('R ')-BPB complexes with alkylcyano bromides (Br(CH2) nCN, n = 2-4). Enantiomerically enriched ('S')- and ('R')-nitrile amino acids (84-96% e.e.) obtained by acid hydrolysis of the alkylated complexes were recrystallized to yield enantiomerically pure nitrile amino acids (>99% e.e.). The diastereoselectivity of the alkylation reaction and enantiomeric purity of the nitrile amino acids was determined by HPLC analysis of diastereomeric, fluorescent derivatives. Optical rotations were used to assign stereochemical configurations. The corresponding ('S')- and ('R')-diamino acids were produced in a single step by reducing the nitrile group of the nitrile amino acids.
ISBN
0494008350
9780494008355