Prosekin

General info

Original publication	Girard, 2021
Original source	Pseudomonas prosekii LMG 26287T
Other known sources (non-putative)	n.a.
Stereochemistry determined by	n.a.

Chemical properties

CAS	n.a.
Molecular formula	C52H92N8O14
Molecular weight	1053.4 g/mol
Mono-isotopic mass	1052.6733 Da
Solubility	n.a.
CMC	n.a.
Minimal surface tension	n.a.
NMR data available in literature	DMF-d7 (Girard, 2021)

Introduction

Prosekin was isolated from the Antarctic isolate Pseudomonas prosekii LMG 26287^T in the context of a study into the export systems of Pseudomonas lipopeptides. More specifically, Girard et al. revealed a strong correlation of the phylogeny of the PleB transporter – partly driving export of Pseudomonas LPs – with CLiP chemical diversity. Specifically, the authors concluded that PleB is suitable as a diagnostic sequence for genome mining, allowing assignment of the putative metabolite to a particular LP family. By applying this approach, the sequence of the Bananamide group member prosekin was predicted and characterized.

Chemical structure

The structure of prosekin has been determined by NMR spectroscopy and mass spectrometry. This compound features an amino acid sequence composed of 8 amino acids, of which 6 are involved in the macrocycle, and thus structurally belongs to the Bananamide family. Prosekin has a saturated fatty acid moiety, 3-hydroxydecanoate (3-OH C10:0). Compared with the family’s namesake LP bananamide, prosekin features an Ile at position 7 (instead of Leu), a Glu at position 2 like MDN-0066 (instead of Asp for bananamides A to G) and a Ser at position 6 (instead of Gln for bananamides A to C). The sequence of prosekin is thus 3-OH C10:0 – Leu – Glu – Thr – Leu – Leu – Ser – Ile – Ile.

NMR Fingerprint matching

References

Girard, et al. “Transporter gene-mediated typing for detection and genome mining of lipopeptide-producing Pseudomonas.” Applied Environmental Microbiology (2021): https://dx.doi.org/10.1128/aem.01869-21.