PhD Scientific Days 2026

Poster Session 2.G - Pharmaceutical Sciences and Health Technologies

Synthesis and unambiguous assignment of absolute configurations for bacillamide B–D and neobacillamide A alkaloids, and their antipodes

Előadó neve

Pollák, Patrik

Neptune code

QDQ5IR

Előadó munkahelye

Egis Pharmaceuticals Plc.

Előadó telefonszáma

06203791333

Előadó e-mail címe

pollakpatrik.chem@gmail.com

Az előadás címe

Synthesis and unambiguous assignment of absolute configurations for bacillamide B–D and neobacillamide A alkaloids, and their antipodes

Szerző(k) neve és munkahelye

Patrik Pollák¹

1: Egis Pharmaceuticals Plc.

Bemutatás módja

Poszter

Szekció

Poster Session 2.G - Pharmaceutical Sciences and Health Technologies

Language of the presentation

Hungarian

Preferred session

Pharmaceutical Sciences and Health Technologies

Összefoglaló szövege

The increasing frequency of algal blooms in aquatic ecosystems has intensified interest in bacillamide alkaloids due to their notable algicidal properties.[1,2] During a critical review of the literature, we identified several inconsistencies and contradictory reports concerning the absolute configuration and the optical rotation of both naturally isolated and synthetically prepared bacillamides.
To resolve these issues, we developed a new enantioselective synthesis of bacillamides B–D, neobacillamide A, and their antipodes, starting from the respective enantiomers of 2-(1-hydroxy)ethyl-thiazole. This synthetic route enables the efficient and stereocontrolled preparation of all target compounds, including their antipodes.
Crucially, single-crystal X-ray diffraction (XRD) analysis of the picrate salt of (–)-bacillamide D provided an unambiguous assignment of its absolute configuration. Using this result as a stereochemical reference point, we reliably determined the absolute configurations and directions of optical rotation for the entire series of synthesized bacillamides and their enantiomers. Chiral HPLC methods has also been developed to confirm the enantiomeric excess (ee) for all alkaloids and their enantiomers.
Our findings correct earlier misassignments in the literature and provide a definitive structure–chirality–optical rotation correlation for this class of bioactive natural products. The clarified stereochemical data are essential for a deeper understanding of structure–activity relationships and for the future design of analogues with enhanced biological efficacy.

References:
[1] Wang, B.; Tao, Y.; Liu, Q.; Liu, N.; Jin, Z.; Xu, X. Mar. Drugs 2017, 15, 247.
[2] Wang, Y.; Liu, Q.; Wei, Z.; Liu, N.; Li, Y.; Li, D.; Jin, Z.; Xu, X. Sci. Rep. 2018, 8, 8555.

University

Semmelweis University

Supervisor

Dr. Balázs Volk and Dr. Mátyás Milen

Publication of my abstract

I give consent to the publication of my abstract on the website of the congress.

phd.section.field

after finishing doctoral studies with absolutorium (PhD)

Kind

Szabad

Status

elfogadva

Accepted presentation method

poszter

Előadás fájl jóváhagyás

nem rendelkezett róla

Előadó

7362

Start

19:06

End

19:09