Related Experiment Video
Updated: Apr 16, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Elucidation of the Guanitrypmycin Biosynthetic Pathway in Kitasatospora azatica Leading to Structure Revision and
1Philipps-Universität Marburg, Fachbereich Pharmazie, Institut für Pharmazeutische Biologie und Biotechnologie, Robert-Koch-Straße 4, Marburg 35037, Germany.
Abstract:
A recently reported incorrect structure revision and assignment of guanitrypmycins raised our attention and encouraged us to clarify the disagreement with additional experimental data. Genome mining of Kitasatospora azatica revealed the presence of a biosynthetic gene cluster for guanitrypmycin-type alkaloids. Expression of this silent cluster in Streptomyces albus led to the identification of two cyclo-l-Trp-l-Trp (1) adducts with guanine (2a and 2b) and two with hypoxanthine (3a and 3b). Detailed NMR analysis and comparison with the published data proved that compound 2a, which was misassigned to guanitrypmycin C3-1 with an N1-C8' connection in a previous report, corresponds to guanitrypmycin D3 with a C2-C8' connection, obtained by a precursor-directed biotransformation. The NMR data of 3b differ clearly from those of guanitrypmycin C3-4 with a C3-C2' connection published in 2019 and correspond very well to those of an allegedly revised guanitrypmycin C3-4 with a C3-C8' connection published in 2024. We therefore corrected this revision and named 3b guanitrypmycin C3-5.
More Related Videos
09:04A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
09:08From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028
Published on: January 13, 2017
Related Concept Videos
Biosynthesis of Nucleic Acids
Amino Acid Biosynthetic Pathways
Inorganic Nitrogen Assimilation
Allosteric Proteins-ATCase
Aspartate transcarbamoylase (ATCase) is a cytosolic enzyme that catalyzes the condensation of L-aspartate and carbamoyl phosphate to N-carbamoyl-L-aspartate. This reaction is the first step in pyrimidine biosynthesis. UTP and CTP, the end products of the pyrimidine synthesis...
Peptidoglycan Synthesis