7SAG

Solution NMR structure of barrettide C

Summary for 7SAG

• Entry DOI: 10.2210/pdb7sag/pdb
• NMR Information: BMRB: 30952
• Descriptor: Barrettide C (1 entity in total)
• Functional Keywords: antifouling, marine natural product, toxin
• Biological source: Geodia barretti
• Total number of polymer chains: 1
• Total formula weight: 3245.55

Authors

Payne, C.D.,Rosengren, K.J. (deposition date: 2021-09-22, release date: 2022-01-12, Last modification date: 2024-10-23)

Primary citation

Steffen, K.,Laborde, Q.,Gunasekera, S.,Payne, C.D.,Rosengren, K.J.,Riesgo, A.,Goransson, U.,Cardenas, P.
Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti .
J.Nat.Prod., 84:3138-3146, 2021

PubMed Abstract: Natural product discovery by isolation and structure elucidation is a laborious task often requiring ample quantities of biological starting material and frequently resulting in the rediscovery of previously known compounds. However, peptides are a compound class amenable to an alternative genomic, transcriptomic, and discovery route by similarity searches of known peptide sequences against sequencing data. Based on the sequences of barrettides A and B, we identified five new barrettide sequences (barrettides C-G) predicted from the North Atlantic deep-sea demosponge (Geodiidae). We synthesized, folded, and investigated one of the newly described barrettides, barrettide C (NVVPCFCVEDETSGAKTCIPDNCDASRGTNP, disulfide connectivity I-IV, II-III). Co-elution experiments of synthetic and sponge-derived barrettide C confirmed its native conformation. NMR spectroscopy and the anti-biofouling activity on larval settlement of the bay barnacle (IC 0.64 μM) show that barrettide C is highly similar to barrettides A and B in both structure and function. Several lines of evidence suggest that barrettides are produced by the sponge itself and not one of its microbial symbionts.

PubMed: 34874154
DOI: 10.1021/acs.jnatprod.1c00938

Experimental method

SOLUTION NMR