ORCID

0000-0002-7811-1339

Keywords

natural product biosynthesis, nitrogen-nitrogen bond

Subject Categories

Biochemistry | Molecular Biology

Abstract

N-Nitroglycine (NNG) is a nitramine [R(R′)N–NO2; R′=H or alkyl] natural product (NP) produced by certain actinomycetes, such as Streptomyces noursei. At the beginning of this project, the biosynthesis of this NP was unknown. The goal was to determine how NNG and its nitramine moiety are enzymatically formed. This could lead to the discovery of novel nitramine NPs with diverse applications as well as alternative/green synthesis of nitramine explosives. This work begins by examining diverse biochemical N–N bond formation strategies. Nitrogen cycle enzymes, nitration of NPs, kutzneride biosynthesis, the aspartate/nitrosuccinate superfamily, hydrazinoacetic acid (HAA) biosynthesis, and streptozocin biosynthesis are among the topics discussed en route to developing a hypothesis and experimental design for the project. This discussion leads to the performance of a combination of stable isotope labeling assays, genome mining, recombinant expression, and in vitro characterization experiments. It was determined that HAA is a precursor for NNG, along with which enzymes are responsible for forming HAA, and what the biosynthetic gene cluster (BGC) of NNG is. The work finishes by performing bioinformatic analysis of the NNG BGC and proposing the full biosynthetic pathway for NNG.

Completion Date

2026

Semester

Summer

Committee Chair

Caranto, Jonathan

Degree

Doctor of Philosophy (Ph.D.)

College

College of Sciences

Department

Chemistry

Format

PDF

Document Type

Dissertation

Language

English

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