H2020Индивидуална стипендия2019–2021

ELECTROSULF · Electrochemical Sulfonylation of Lysine Residues in Continuous Flow Microreactors.

„Хоризонт 2020“ — Действия „Мария Склодовска-Кюри“

Период: 2019-09-05 → 2021-09-04
Финансиране от ЕС: 175 572 €
Участници: 1
Схема: MSCA-IF-EF-ST

Линиите свързват координатора с партньорите.

Накратко на български

Електрохимичният синтез в микрореактори позволява по-бързо и чисто модифициране на молекули, като например добавянето на азотни групи към арени. Този подход намалява времето за реакция и избягва използването на метални катализатори, което прави индустриалните процеси по-ефективни и екологични.

Този кратък обзор е генериран от изкуствен интелект

Кратко обяснение, генерирано от езиков модел по текста на CORDIS. Оригиналът е по-долу.

Резултати накратко

Electrochemical Sulfonylation of Lysine Residues in Continuous Flow Microreactors.

Electrochemistry has become an important tool for organic chemists as it allows to selectively functionalize molecules by tuning the applied voltage, without the addition of strong oxidant/reductant agents. As electrons are considered green reagents and not harsh conditions are generally involved, synthetic electrochemistry can be seen environmentally friendly. Although known for centuries, this technique has only recently become an intriguing possibility for scientists, and it gets explored more and more, due to modern technological advances. In this sense, continuous-flow chemistry with its benefits (better heat- and mass transfer, higher productivity, etc.) can significantly contribute to the development of new more efficient transformations, also in a bigger scale. The combination of electrochemistry and continuous-flow technology could have a strong impact in synthetic chemistry, with important consequences for the industrial sets up too. In fact, the development of new electrochemical synthesis in flow is important as it might contribute to an industrial shift towards more efficient processes and thus to a more sustainable society. Taking this in consideration, the aim of my project was to learn how to use the electrochemical microflow reactor to find and tune new reactivities. Although the first attempts were unsuccessful, I finally managed to optimize and develop the electrochemical azolation of arenes in flow, proving once more the great potential of electrochemistry in flow. Compared to other azolation methods, electrochemistry does not require neither metal nor organic catalyst; moreover, the reaction time can be reduced to 10 min in flow, instead of several hours in batch.

Текст от CORDIS, на английски · Данни: CORDIS, © Европейски съюз

Цел на проекта

Peptides are important molecules, ubiquitous in biological systems. Their relevance in the pharmaceutical sector is proven by the constant increase which the global market of peptide-based drugs is experiencing in the last years. As a consequence, several methods have been developed to modify peptides (e.g. condensation, cross-coupling, transition-metal catalysis, and photocatalysis), being lysine with its free amine one of the most preferred handles used by chemists to introduce a new moieties, e.g. cytotoxic drugs or fluorescent labels. Several transformations as alkylation, arylation, oxidation, acylation and condensation have been described for lysine. However, it would be very appealing to introduce selectively a sulfonyl group, which would result in the formation of a sulfonamide, a functionality which is widely employed in drugs. Although several oxidative sulfonylations are reported in the literature, their drawbacks motivate me to look for greener synthetic strategies. Electrosynthesis represents an advantageous alternative, which has been re-discovered in the last years also thanks to its employment in continuous-flow microreactors. With the support of this modern technology, it is possible to minimize the difficulties connected to older electrochemical processes (such as mass-transfer limitation, the need of a supporting electrolyte,and the difficult scale-up). ELECTROSULF aims at developing a novel sulfonylation of lysine by electrochemical means with the use of a flow microreactor. The reaction mechanism will be also properly studied. My strong background in organic chemistry together with Prof. Timothy Noël’s expertise in flow processes and reaction miniaturization will guarantee the success of ELECTROSULF, whose achievement will have a great impact on the pharmaceutical sector, paving the path to a new approach for peptide modification.

Оригинален текст от CORDIS (на английски).

Участници

TECHNISCHE UNIVERSITEIT EINDHOVEN · EindhovenКоординаторНидерландия