Synthesis of acetamides extracted from the Marine Bibalve Codakia orbicularis

Synthesis of acetamides extracted from the Marine Bibalve Codakia orbicularis (Lucinidae)

Réf ABG-134068

Stage master 2 / Ingénieur

Durée 5 mois

Salaire net mensuel gratification

28/10/2025

Institut National des Sciences Appliquées de Lyon

Lieu de travail

Villeurbanne Auvergne-Rhône-Alpes France

Champs scientifiques

• Chimie

Établissement recruteur

The "Laboratoire de Chimie Organique et Bioorganique" of the Institut National des

Sciences Appliquées de Lyon belongs to ICBMS (Institut de Chimie et Biochimie

Moléculaires et Supramoléculaires, ICBMS; webpage: , UMR-CNRS

5246) and is developing innovative research projects at the chemistry-biology interface

associated with methodology, glycochemistry and multistep organic synthesis dedicated to

molecules of therapeutic interest or used in the design of new materials

The team projects are devoted to the development of new synthetic methodology and

its applications to new heterocyclic scaffolds targeting a wide range of enzymes / receptors.

Research is pointing out the development of new heterocyclic scaffolds

using transition metal complexes and their applications to the synthesis of molecules

focusing on pharmaceutical targets (inflammation, anti-coagulants, anti-bacterial agents,

cancer).

Description

The marine bivalve Codakia orbicularis, harbors endosymbiotic bacteria located in its gill filaments.

Bioassay-guided fractionation of an ethyl acetate extract of the gill tissues led to antibacterial fractions (against

Gram positive and negative bacteria). The bioactive fractions were analyzed using standard chromatographic and

spectrometric methods, revealing in particular a ceramide-like compound isolated for the first time in the

biosphere

In collaboration with our partner in Université des Antilles, Guadeloupe (Dr. F. Goudou & Dr. O. Gros),

the objectives of this internship will address the synthesis of several analogues of this metabolite, for a further

evaluation of their antibacterial activity and putative relationships with structural variations. Indeed different

modifications might be carried out including the degree of hydroxylation, the stereochemistry of the two

stereogenic centers, the length of aliphatic chain and the nature of the fatty acid moiety (Figure 1b).

Whilst many different routes to substituted sphingolipids have been reported, including asymmetric

strategies, alternative sequences will be sought with highly selective steps that might minimize tedious

purification strategies. Aware that variation in the sphingosine core and fatty acid alkyl chains could be

introduced by simple cross metathesis and amine acylation respectively, the generation of a set of

hydroxybutenyl aminoalcohol core scaffolds will be targeted starting from readily available -amino acids.

Benefitting from our experience in multi-step organic synthesis, the intern will specially develop valuable skills in

organic chemistry and for example will be able:

• To optimize conditions according to the parameters screened in synthetic methodology
• To characterize structurally complex molecules according classical routine analytical methods skills (1D and 2D

NMR, mass spectrometry, IR).

• To clearly communicate the results, both in writing in a lab book, in short reports and orally in weekly meetings

Profil

The position will be available for five to six months. Appropriate background should include experience in multi-step

organic synthesis and associated analytical skills (NMR, MS, GC, HPLC, UV) will be

appreciated. A good expertise in homonuclear and heteronuclear (1D & 2D) NMR as well as

in the use of classical spectroscopic techniques will also be required. Applications will be

considered from candidates who have (or are expected to obtain) a good degree and level in

organic chemistry.

Prise de fonction

Dès que possible

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