Methods of Non-a-Amino Acid Synthesis, 2nd Edition

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

3

–C

10

, 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

Synthesis

Methods of Non-α-Amino Acid Synthesis

Michael Bryant Smith

Smith

Second Edition

Second

Edition

Organic Chemistry

K16816

K16816_Cover.indd 1 9/27/13 3:02 PM

Methods of

Non-a-Amino Acid

Synthesis

Second Edition

Methods of

Non-a-Amino Acid

Synthesis

Michael Bryant Smith

University of Connectitcut

Storrs, USA

Second Edition

CRC Press

Taylor & Francis Group

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