Structural aspects of phenylglycines, their biosynthesis and occurrence in peptide natural products

Covering up to February 2015 Phenylglycine-type amino acids occur in a wide variety of peptide natural products, including glycopeptide antibiotics and biologically active linear and cyclic peptides. Sequencing of biosynthesis gene clusters of chloroeremomycin, balhimycin and pristinamycin paved the...

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Bibliographic Details
Published in:Natural product reports 2015-08, Vol.32 (8), p.127-1235
Main Authors: Al Toma, Rashed S, Brieke, Clara, Cryle, Max J, Süssmuth, Roderich D
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Amino Acids - metabolism
Biological Products - chemistry
Biological Products - metabolism
Glycine - analogs & derivatives
Glycine - chemistry
Glycine - metabolism
Molecular Structure
Peptides - chemistry
Peptides - metabolism
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Summary:Covering up to February 2015 Phenylglycine-type amino acids occur in a wide variety of peptide natural products, including glycopeptide antibiotics and biologically active linear and cyclic peptides. Sequencing of biosynthesis gene clusters of chloroeremomycin, balhimycin and pristinamycin paved the way for intensive investigations on the biosynthesis of 4-hydroxyphenylglycine (Hpg), 3,5-dihydroxyphenylglycine (Dpg) and phenylglycine (Phg) in recent years. The significance and importance of this type of unusual non-proteinogenic aromatic amino acids also for medicinal chemistry has drawn the attention of many research groups and pharmaceutical companies. Herein structures and properties of phenylglycine containing natural products as well as the biosynthetic origin and incorporation of phenylglycines are discussed. Phenylglycine-type amino acids occur in a wide variety of peptide natural products. Herein structures and properties of these peptides as well as the biosynthetic origin and incorporation of phenylglycines are discussed.
ISSN:0265-0568
1460-4752
DOI:10.1039/c5np00025d