Bananamides 1 – 3

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General info

Original publicationNguyen, 2016
Original sourcePseudomonas fluorescens BW11P2
Other known sources (non-putative)
Stereochemistry determined byNot determined

Chemical properties

CAS
Molecular formulaC55H97N9O14
Molecular weight1108.4 g/mol
Mono-isotopic mass1107.7155 Da
Solubility
CMC
Minimal surface tension
3D conformation
NMR data available in literatureMethanol-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.

Primary structure of bananamide 1.

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

Bananamide 2 – PubChem or NORINE database

Bananamide 3 – PubChem or NORINE database

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