Although less common than α-amino acids, non-α-amino acids—
where the amino group is not on the carbon immediately adjacent
to the carboxyl group but is attached to another carbon in the chain
(for example, the β, γ, δ carbon)—are components of biologically
important molecules, are signicant in the pharmaceutical industry,
and are useful starting materials for many areas of organic chemistry.
Since the publication of the rst edition of this book nearly 20 years
ago, synthetic work devoted to the preparation of non-α-amino
acids has expanded greatly.
Methods of Non-α-Amino Acid Synthesis, Second Edition has
been extensively rewritten and reorganized, providing an up-to-date
review of strategies and methods for non-α-amino acid synthesis,
particularly those amino acids that are key synthetic intermediates
or important compounds in their own right. It focuses on acyclic
amino acids of C
, but also aminoalkanoic carboxylic acids,
aminoalkenoic acids, and aminoalkynoic acids. The new edition
contains many updated references and has a greater emphasis on
the biological importance of non-α-amino acids. In addition to an
array of synthetic methods, the book offers discussions on why
non-α-amino acids are important.
The book covers synthetic methods that rely on substituent
refunctionalization, the conversion of cyclic precursors to acyclic
amino acids, conjugate addition reactions, and enolate anion
reactions and condensation reactions that lead to non-α-amino
acids. It also examines reactions and strategies that lead to good
diastereoselectivity and enantioselectivity during synthesis. A
chapter devoted to biologically important amino acids includes
separate sections on GABA, GABOB, carnitine, DAVA, statine, and
other signicant amino acids as well as a new section on peptides
and proteins that contain non-α-amino acids. The nal chapter
addresses aminocyclic and heterocyclic amino acids.
Methods of
Non-α-Amino Acid
Methods of Non-α-Amino Acid Synthesis
Michael Bryant Smith
Second Edition
Organic Chemistry
K16816_Cover.indd 1 9/27/13 3:02 PM
Methods of
Non-a-Amino Acid
Second Edition
Methods of
Non-a-Amino Acid
Michael Bryant Smith
University of Connectitcut
Storrs, USA
Second Edition
CRC Press
Taylor & Francis Group
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Boca Raton, FL 33487-2742
© 2014 by Taylor & Francis Group, LLC
CRC Press is an imprint of Taylor & Francis Group, an Informa business
No claim to original U.S. Government works
Version Date: 20130719
International Standard Book Number-13: 978-1-4665-7792-3 (eBook - PDF)
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