Discovery of Acyl-Surugamide A2 from Marine Streptomyces albidoflavus RKJM-0023-A New Cyclic Nonribosomal Peptide Containing an N-ε-acetyl-L-lysine Residue

Zacharie A Maw; Bradley Haltli; Jason J Guo; Donna M Baldisseri; Christopher Cartmell; Russell G Kerr

doi:10.3390/molecules29071482

Discovery of Acyl-Surugamide A2 from Marine Streptomyces albidoflavus RKJM-0023-A New Cyclic Nonribosomal Peptide Containing an N-ε-acetyl-L-lysine Residue

Molecules. 2024 Mar 27;29(7):1482. doi: 10.3390/molecules29071482.

Authors

Zacharie A Maw¹, Bradley Haltli^{1

2}, Jason J Guo³, Donna M Baldisseri⁴, Christopher Cartmell⁵, Russell G Kerr^{1

2

6}

Affiliations

¹ Department of Biomedical Sciences, Atlantic Veterinary College, University of Prince Edward Island, Charlottetown, PE C1A 4P3, Canada.
² Nautilus Biosciences, Croda Canada Limited, Charlottetown, PE C1A 4P3, Canada.
³ Department of Chemistry & Chemical Biology, Barnett Institute for Chemical and Biological Analysis, Northeastern University, Boston, MA 02115, USA.
⁴ Bruker Biospin Corp., 15 Fortune Drive, Billerica, MA 01821, USA.
⁵ Department of Pharmacology, Comprehensive Center for Pain & Addiction, College of Medicine, University of Arizona, Tucson, AZ 85724, USA.
⁶ Department of Chemistry, University of Prince Edward Island, Charlottetown, PE C1A 4P3, Canada.

Abstract

We report the discovery of a novel cyclic nonribosomal peptide (NRP), acyl-surugamide A2, from a marine-derived Streptomyces albidoflavus RKJM-0023 (CP133227). The structure of acyl-surugamide A2 was elucidated using a combination of NMR spectroscopy, MS2 fragmentation analysis, and comparative analysis of the sur biosynthetic gene cluster. Acyl-surugamide A2 contains all eight core amino acids of surugamide A, with a modified N-ε-acetyl-L-lysine residue. Our study highlights the potential of marine Streptomyces strains to produce novel natural products with potential therapeutic applications. The structure of cyclic peptides can be solved using MS2 spectra and analysis of their biosynthetic gene clusters.

Keywords: GNPS; Streptomyces; acyl-surugamide A2; cyclic nonribosomal peptide; cyclic peptide; marine Streptomyces; natural products; nonribosomal peptide; surugamide.

MeSH terms

Amino Acids
Lysine*
Peptides, Cyclic
Streptomyces* / genetics

Substances

Lysine
Amino Acids
Peptides, Cyclic

Supplementary concepts

Streptomyces albidoflavus

Grants and funding

We gratefully acknowledge financial support from the Natural Sciences and Engineering Research Council of Canada (605010), the Canada Foundation for Innovation, and the Jean and Jean-Louis Lévesque Foundation.