The expanding spectrum of diketopiperazine natural product biosynthetic pathways containing cyclodipeptide synthases

P Borgman, RD Lopez, AL Lane - Organic & biomolecular chemistry, 2019 - pubs.rsc.org
Microorganisms are remarkable chemists, with enzymes as their tools for executing multi-
step syntheses to yield myriad natural products. Microbial synthetic aptitudes are illustrated …

Guanitrypmycin Biosynthetic Pathways Imply Cytochrome P450 Mediated Regio‐and Stereospecific Guaninyl‐Transfer Reactions

J Liu, X **e, SM Li - Angewandte Chemie International Edition, 2019 - Wiley Online Library
Mining microbial genomes including those of Streptomyces reveals the presence of a large
number of biosynthetic gene clusters. Unraveling this genetic potential has proved to be a …

Genome mining of cyclodipeptide synthases unravels unusual tRNA-dependent diketopiperazine-terpene biosynthetic machinery

T Yao, J Liu, Z Liu, T Li, H Li, Q Che, T Zhu, D Li… - Nature …, 2018 - nature.com
Cyclodipeptide synthases (CDPSs) can catalyze the formation of two successive peptide
bonds by hijacking aminoacyl-tRNAs from the ribosomal machinery resulting in …

Two Cytochrome P450 Enzymes from Streptomyces sp. NRRL S-1868 Catalyze Distinct Dimerization of Tryptophan-Containing Cyclodipeptides

H Yu, SM Li - Organic letters, 2019 - ACS Publications
Heterologous expression in Streptomyces coelicolor and in vitro enzyme characterization
proved that two P450 enzymes, AspB and NasB, from Streptomyces sp. NRRL S-1868 …

Elucidation of the Streptoazine Biosynthetic Pathway in Streptomyces aurantiacus Reveals the Presence of a Promiscuous Prenyltransferase/Cyclase

J Liu, Y Yang, L Harken, SM Li - Journal of Natural Products, 2021 - ACS Publications
Heterologous expression of a three-gene cluster from Streptomyces aurantiacus coding for a
cyclodipeptide synthase, a prenyltransferase, and a methyltransferase led to the elucidation …

Double the chemistry, double the fun: Structural diversity and biological activity of marine-derived diketopiperazine dimers

NGM Gomes, RB Pereira, PB Andrade, P Valentão - Marine drugs, 2019 - mdpi.com
While several marine natural products bearing the 2, 5-diketopiperazine ring have been
reported to date, the unique chemistry of dimeric frameworks appears to remain neglected …

Widely Distributed Bifunctional Bacterial Cytochrome P450 Enzymes Catalyze both Intramolecular C−C Bond Formation in cyclol‐Tyr‐l‐Tyr and Its Coupling with …

J Liu, L Harken, Y Yang, X **e… - Angewandte Chemie …, 2022 - Wiley Online Library
Tailoring enzymes are important modification biocatalysts in natural product biosynthesis.
We report herein six orthologous two‐gene clusters for mycocyclosin and guatyromycine …

Coupling of Guanine with cyclo-l-Trp-l-Trp Mediated by a Cytochrome P450 Homologue from Streptomyces purpureus

H Yu, X **e, SM Li - Organic letters, 2018 - ACS Publications
A cyclo-l-Trp-l-Trp tailoring P450 with novel function from Streptomyces purpureus was
identified by heterologous expression in S. coelicolor and in vitro assays the recombinant …

Production of Diketopiperazine Derivatives by Pathway Engineering with Different Cyclodipeptide Synthases from Various Streptomyces Strains

SA Stierle, L Harken, SM Li - ACS Synthetic Biology, 2023 - ACS Publications
Cyclodipeptides from fungi and bacteria are often modified by different tailoring enzymes.
They display various biological and pharmacological activities, and some derivatives are …

Increasing cytochrome P450 enzyme diversity by identification of two distinct cyclodipeptide dimerases

J Liu, X **e, SM Li - Chemical Communications, 2020 - pubs.rsc.org
Genome mining revealed the presence of two cdps-p450 operons in Saccharopolyspora
antimicrobica. Heterologous expression, biochemical characterisation and structure …