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Bananamides 1 – 3
General info
| Original publication | Nguyen, 2016 |
| Original source | Pseudomonas fluorescens BW11P2 |
| Other known sources (non-putative) | – |
| Stereochemistry determined by | Not determined |
Chemical properties
| CAS | – |
| Molecular formula | C55H97N9O14 |
| Molecular weight | 1108.4 g/mol |
| Mono-isotopic mass | 1107.7155 Da |
| Solubility | – |
| CMC | – |
| Minimal surface tension | – |
| 3D conformation | – |
| NMR data available in literature | Methanol-d4 (Nguyen, 2016) |
Introduction
Bananamides 1, 2 and 3 were discovered by indexing the pseudomonas metabolome through the molecular networking of mass spectrometric sequence tags. Their producing bacterium, Pseudomonas fluorescens BW11P2, was collected from the banana rhizoplane in the wetlands of Galagedara (Sri Lanka) and represents the only non-putative source of bananamides 1 – 3 to date.
Chemical structure
Using MS/MS and liquid state NMR spectroscopy, it was determined that bananamides 1, 2 and 3 all have an identical amino acid sequence, being Leu1 – Asp2 – Thr3 – Leu4 – Leu5 – Gln6 – Leu7 – Ile8, whereby the molecule is cyclized by means of an ester bond between the C-terminal carbonyl carbon of the side chain hydroxyl moiety of Thr3. Both compound differ only in their N-terminal fatty acid moiety, being 3-hydroxy dodecanoic acid (3-OH C12:0), 3-hydroxy dodecenoic acid (3-OH C12:1) and 3-hydroxy decanoic acid (3-OH C10:0) respectively. No information is available concerning the stereochemistry of the individual amino acids.
They are the namesake CLiPs of the bananamide group; a collection of structurally similar cyclic lipodepsipeptides such as MDN-0066 and bananamides D – G.
NMR fingerprint data
Recently, it was established that the planar structure and stereochemistry of CLiPs can be assessed by simple comparison to a reference. (De Roo, 2022) More specifically, by matching NMR spectra of a CLiP from a newly isolated bacterial source with those of existing (reference) CLiPs, one can determine whether they are identical or not. A detailed explanation on what NMR fingerprint matching is, and how to use it, can be found here.
Below, we provide the reference NMR data of bananamide I, II and III (also called A, B and C) in an Excel format. This data is recorded in methanol at room temperature, and can be used to asses similarities of newly isolated CLiPs to bananamides I to III.
References
Nguyen, et al. “Indexing the Pseudomonas specialized metabolome enabled the discovery of poaeamide B and the bananamides.” Nature Microbiology2 (2016): https://dx.doi.org/10.1038/nmicrobiol.2016.197.
De Roo, et al. “An nuclear magnetic resonance fingerprint matching approach for the identification and structural re-evaluation of Pseudomonas lipopeptides.” Microbiology Spectrum (2022) https://dx.doi.org/doi:10.1
External links
Bananamide 1 – PubChem or NORINE database