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7
Synergies of Chemistry and Biochemistry for the Production of
-Amino Acids

Josefa Mar´ ıa Clemente-Jim´ enez, Sergio Mart´ ınez-Rodr´ ıguez, Felipe Rodr´ ıguez-Vico, and
Francisco Javier Las Heras-V´ azquez

7.1
Introduction

β-Amino acids have attracted increasing attention over recent years as they play a
key role in chemical biology, the synthesis of natural products, and the manufacture
of drugs. Contrary to proteinogenic α-amino acids, β-amino acids only occur as
constituents of natural products and are often characterized by important biological
and physiological activities [1]. In consequence, β-amino acids are constituents of
several natural products such as taxol, dolastatins, jasplakinolide, theopalauam-
mide, and many others [2]. β-Amino acids have been also used as building blocks of
peptides, peptidomimetics, and many other physiologically active compounds [3].
Furthermore, β-amino acids show interesting pharmacological properties in their
free form [2], or as their cyclized (β-lactam) derivates [4]. β-Alanine, a natural β-
amino acid, is a precursor of coenzyme A (CoA) and pantothenic acid in bacteria and
fungi (vitamin B5) [5]. β-Alanine is widely distributed in the central nervous system
of vertebrates and is a structural analog of the major inhibitory neurotransmitters
γ-amino-n-butyric acid (GABA) and glycine, suggesting that it may be involved
in synaptic transmissions [6]. In the field of sports, β-alanine supplementation
increases muscle buffer capacity in humans, thus potentially enhancing physical
performance during high intensity exercise while also delaying the onset of neuro-
muscular fatigue [7, 8]. Taurine (2-aminoethanesulfonic acid) is another important
natural β-amino acid which exerts a variety of biological actions that may maintain
physiological homeostasis, and recent data have shown the effectiveness of taurine
supplementation against insulin resistance as well as both insulin dependent and
non-insulin dependent diabetes mellitus [9]. 2-Aminoethylphosphonate (2-AEP),
the most common naturally occurring phosphonate, also known as ciliatine,isan
important precursor used in the biosynthesis of phosphonolipids, phosphonopro-
teins, and phosphonoglycans [10]. β-Homoalanine (3-aminobutyric acid, 3-ABA)
is employed for plant protection in sustainable agriculture as a plant activator
against various pathogens by means of a natural defense mechanism known as
induced resistance [11, 12]. β-Aminoisobutyric acid (α-methyl-β-alanine, 3-AiBA) has

Cascade Biocatalysis: Integrating Stereoselective and Environmentally Friendly Reactions, First Edition.
Edited by Sergio Riva and Wolf-Dieter Fessner.
c 2014 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2014 by Wiley-VCH Verlag GmbH & Co. KGaA.