4.8 Article

Identification of the Azaserine Biosynthetic Gene Cluster Implicates Hydrazine as an Intermediate to the Diazo Moiety

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Biosynthesis of Tasikamides via Pathway Coupling and Diazonium-Mediated Hydrazone Formation

Guang-Lei Ma et al.

Summary: Naturally occurring hydrazones are rare, but widely used in the synthesis of organic compounds and functional materials. In this study, a novel family of microbial metabolites, tasikamides, was discovered. These tasikamides have a unique cyclic pentapeptide scaffold and contain a hydrazone group. The biosynthesis of tasikamides was found to require two gene clusters, one for the cyclic peptide scaffold and another for the synthesis of alkyl 5-hydroxylanthranilate. The findings revealed a novel mechanism for the formation of specialized metabolites through the coupling of two biosynthetic pathways.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

A Natural Dihydropyridazinone Scaffold Generated from a Unique Substrate for a Hydrazine-Forming Enzyme

Kenichi Matsuda et al.

Summary: Functional groups containing nitrogen-nitrogen bonds are uncommon but can be found in a wide range of natural products. Recent research on the biosynthetic pathways of these functional groups has revealed the presence of overlooked biosynthetic genes in bacteria, indicating the existence of unidentified natural products with unique functional groups.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Bacterial Avenalumic Acid Biosynthesis Includes Substitution of an Aromatic Amino Group for Hydride by Nitrous Acid Dependent Diazotization

Seiji Kawai et al.

Summary: The diazo group is an important functional group that can confer biological activity to natural products owing to its high reactivity. This study discovered a new diazo group biosynthesis gene cluster and revealed an unprecedented pathway for amino group removal via diazotization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Complete Biosynthetic Pathway of Alazopeptin, a Tripeptide Consisting of Two Molecules of 6-Diazo-5-oxo-l-norleucine and One Molecule of Alanine

Seiji Kawai et al.

Summary: The study revealed the complete biosynthetic pathway of Alazopeptin, elucidating the synthesis pathways of DON and its derivative N-acetyl DON, enriching the enzymology knowledge of N-N bond formation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Biochemistry & Molecular Biology

Biosynthesis of triacsin featuring an N-hydroxytriazene pharmacophore

Antonio Del Rio Flores et al.

Summary: The study identified all enzymes required for constructing and installing the N-hydroxytriazene pharmacophore of triacsins, paving the way for future mechanistic interrogation and biocatalytic application of enzymes for N-N bond formation.

NATURE CHEMICAL BIOLOGY (2021)

Article Chemistry, Medicinal

Direct Alkylation of Deoxyguanosine by Azaserine Leads to O6-Carboxymethyldeoxyguanosine

Susanne M. Geisen et al.

Summary: This study characterized the formation of O-6-CMdG by L-azaserine through a series of chemical and enzymatic studies, providing insights into its role as a chemical probe for DNA damage and mutation research in cancer.

CHEMICAL RESEARCH IN TOXICOLOGY (2021)

Article Biochemistry & Molecular Biology

The Biosynthetic Gene Cluster of Pyrazomycin-A C-Nucleoside Antibiotic with a Rare Pyrazole Moiety

Guiyun Zhao et al.

CHEMBIOCHEM (2020)

Article Chemistry, Applied

Thermal Stability and Explosive Hazard Assessment of Diazo Compounds and Diazo Transfer Reagents

Sebastian P. Green et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2020)

Review Biochemistry & Molecular Biology

Recent advance in the biosynthesis of nitrogen-nitrogen bond-containing natural products

Yohei Katsuyama et al.

CURRENT OPINION IN CHEMICAL BIOLOGY (2020)

Article Chemistry, Multidisciplinary

Discovery of Unprecedented Hydrazine-Forming Machinery in Bacteria

Kenichi Matsuda et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Multidisciplinary Sciences

Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin

Kwo-Kwang A. Wang et al.

NATURE COMMUNICATIONS (2018)

Article Multidisciplinary Sciences

Structural and mutational analysis of the nonribosomal peptide synthetase heterocyclization domain provides insight into catalysis

Kristjan Bloudoff et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2017)

Article Biochemistry & Molecular Biology

Structural and functional aspects of the nonribosomal peptide synthetase condensation domain superfamily: discovery, dissection and diversity

Kristjan Bloudoff et al.

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEINS AND PROTEOMICS (2017)

Article Biochemistry & Molecular Biology

A nitrous acid biosynthetic pathway for diazo group formation in bacteria

Yoshinori Sugai et al.

NATURE CHEMICAL BIOLOGY (2016)

Article Multidisciplinary Sciences

Structural elements of an NRPS cyclization domain and its intermodule docking domain

Daniel P. Dowling et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2016)

Article Chemistry, Multidisciplinary

Potassium N-Iodo p-Toluenesulfonamide (TsNIK, Iodamine-T): A New Reagent for the Oxidation of Hydrazones to Diazo Compounds

Simon M. Nicolle et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

Review Oncology

Serine, glycine and one-carbon units: cancer metabolism in full circle

Jason W. Locasale

NATURE REVIEWS CANCER (2013)

Review Medicine, Research & Experimental

Nonribosomal peptide synthetases involved in the production of medically relevant natural products

Elizabeth A. Felnagle et al.

MOLECULAR PHARMACEUTICS (2008)

Article Biochemistry & Molecular Biology

Multienzyme docking in hybrid megasynthetases

Carsten D. Richter et al.

NATURE CHEMICAL BIOLOGY (2008)