title: Biosynthesis of natural products containing β-amino acids.
abstract: Covering: up to January, 2014. We focus here on β-amino acids as components of complex natural products because the presence of β-amino acids produces structural diversity in natural products and provides characteristic architectures beyond those of ordinary α-L-amino acids, thus generating significant and unique biological functions in nature. In this review, we first survey the known bioactive β-amino acid-containing natural products including nonribosomal peptides, macrolactam polyketides, and nucleoside-β-amino acid hybrids. Next, the biosynthetic enzymes that form β-amino acids from α-amino acids and the de novo synthesis of β-amino acids are summarized. Then, the mechanisms of β-amino acid incorporation into natural products are reviewed. Because it is anticipated that the rational swapping of the β-amino acid moieties with various side chains and stereochemistries by biosynthetic engineering should lead to the creation of novel architectures and bioactive compounds, the accumulation of knowledge regarding β-amino acid-containing natural product biosynthetic machinery could have a significant impact in this field. In addition, genome mining of characteristic β-amino acid biosynthetic genes and unique β-amino acid incorporation machinery could lead to the discovery of new β-amino acid-containing natural products.
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551, Japan. fkudo@chem.titech.ac.jp.
authors.forename: Fumitaka
authors.initials: F
authors.lastname: Kudo
authors.forename: Akimasa
authors.initials: A
authors.lastname: Miyanaga
authors.forename: Tadashi
authors.initials: T
authors.lastname: Eguchi
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D001688:Biological Products / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D046908:Peptide Biosynthesis, Nucleic Acid-Independent; D010455:Peptides / Q000737:chemistry / Q000378:metabolism; D061065:Polyketides / Q000378:metabolism; D013237:Stereoisomerism; D013302:Streptomyces / Q000235:genetics / Q000378:metabolism
chemical_list: D000596:Amino Acids; D001688:Biological Products; D010455:Peptides; D061065:Polyketides