Toward the Efficient Synthesis of New Phosphopantothenate Derivatives by Using Chlorophosphate Reagents

Jerca Pahor; Stojan Stavber; Alen Čusak; Gregor Kosec; Hrvoje Petković; Ajda Podgoršek Berke

doi:10.1055/s-0035-1562437

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(21): 3763-3772
DOI: 10.1055/s-0035-1562437

paper

Toward the Efficient Synthesis of New Phosphopantothenate Derivatives by Using Chlorophosphate Reagents

Jerca Pahor

^aLaboratory of Organic and Bioorganic Chemistry, Department of Physical and Organic Chemistry, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia eMail: stojan.stavber@ijs.si

^bJožef Stefan International Postgraduate School, Jamova 39, 1000 Ljubljana, Slovenia

,

Stojan Stavber*

^aLaboratory of Organic and Bioorganic Chemistry, Department of Physical and Organic Chemistry, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia eMail: stojan.stavber@ijs.si

^bJožef Stefan International Postgraduate School, Jamova 39, 1000 Ljubljana, Slovenia

^cCentre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins, Jamova 39, 1000 Ljubljana, Slovenia

,

Alen Čusak

^dAcies Bio d.o.o., Tehnološki Park 21, 1000 Ljubljana, Slovenia

^eAlkemika Ltd., Kukovčeva 1, 3000 Celje, Slovenia

,

Gregor Kosec

^dAcies Bio d.o.o., Tehnološki Park 21, 1000 Ljubljana, Slovenia

,

Hrvoje Petković

^dAcies Bio d.o.o., Tehnološki Park 21, 1000 Ljubljana, Slovenia

,

Ajda Podgoršek Berke

^bJožef Stefan International Postgraduate School, Jamova 39, 1000 Ljubljana, Slovenia

^dAcies Bio d.o.o., Tehnološki Park 21, 1000 Ljubljana, Slovenia

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Abstract

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Abstract

Seven new masked analogues of phosphopantothenate, suitable for an evaluation of their potential ability to restore intracellular coenzyme A (CoA) levels, were successfully synthesized in good to moderate yields. The preparation of derivatives masked with (acyloxy)alkyl groups was studied particularly in terms of synthetic efficiency, and the possibility of applying different chlorophosphate reagents for the preparation of a variety of masked derivatives was also investigated. Using this methodology, we have successfully synthesized a new chlorophosphate reagent, suitable for the introduction of the (isobutyryloxy)methyl functionality into the prodrug. Additionally, special attention was given to finding mild and economical reaction conditions for phosphorylation of biological molecules.

Key words

phosphopantothenate - phosphorylation - chlorophosphate reagents - vitamins - phosphates

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