Synthesis of [(13)C(3)]-B6 Vitamers Labelled at Three Consecutive Positions Starting from [(13)C(3)]-Propionic Acid

[(13)C(3)]-labelled vitamers (PN, PL and PM) of the B6 group were prepared starting from [(13)C(3)]-propionic acid. [(13)C(3)]-PN was synthesized in ten linear steps with an overall yield of 17%. Hereby, higher alkyl homologues of involved esters showed a positive impact on the reaction outcome of t...

Descripción completa

Detalles Bibliográficos
Autores principales: Bachmann, Thomas, Rychlik, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225105/
https://www.ncbi.nlm.nih.gov/pubmed/30142892
http://dx.doi.org/10.3390/molecules23092117
_version_ 1783369698069446656
author Bachmann, Thomas
Rychlik, Michael
author_facet Bachmann, Thomas
Rychlik, Michael
author_sort Bachmann, Thomas
collection PubMed
description [(13)C(3)]-labelled vitamers (PN, PL and PM) of the B6 group were prepared starting from [(13)C(3)]-propionic acid. [(13)C(3)]-PN was synthesized in ten linear steps with an overall yield of 17%. Hereby, higher alkyl homologues of involved esters showed a positive impact on the reaction outcome of the intermediates in the chosen synthetic route. Oxidation of [(13)C(3)]-PN to [(13)C(3)]-PL was undertaken using potassium permanganate and methylamine followed by acid hydrolysis of the imine derivative. [(13)C(3)]-PM could be prepared from the oxime derivative of [(13)C(3)]-PN by hydrogenation with palladium.
format Online
Article
Text
id pubmed-6225105
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62251052018-11-13 Synthesis of [(13)C(3)]-B6 Vitamers Labelled at Three Consecutive Positions Starting from [(13)C(3)]-Propionic Acid Bachmann, Thomas Rychlik, Michael Molecules Article [(13)C(3)]-labelled vitamers (PN, PL and PM) of the B6 group were prepared starting from [(13)C(3)]-propionic acid. [(13)C(3)]-PN was synthesized in ten linear steps with an overall yield of 17%. Hereby, higher alkyl homologues of involved esters showed a positive impact on the reaction outcome of the intermediates in the chosen synthetic route. Oxidation of [(13)C(3)]-PN to [(13)C(3)]-PL was undertaken using potassium permanganate and methylamine followed by acid hydrolysis of the imine derivative. [(13)C(3)]-PM could be prepared from the oxime derivative of [(13)C(3)]-PN by hydrogenation with palladium. MDPI 2018-08-23 /pmc/articles/PMC6225105/ /pubmed/30142892 http://dx.doi.org/10.3390/molecules23092117 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Bachmann, Thomas
Rychlik, Michael
Synthesis of [(13)C(3)]-B6 Vitamers Labelled at Three Consecutive Positions Starting from [(13)C(3)]-Propionic Acid
title Synthesis of [(13)C(3)]-B6 Vitamers Labelled at Three Consecutive Positions Starting from [(13)C(3)]-Propionic Acid
title_full Synthesis of [(13)C(3)]-B6 Vitamers Labelled at Three Consecutive Positions Starting from [(13)C(3)]-Propionic Acid
title_fullStr Synthesis of [(13)C(3)]-B6 Vitamers Labelled at Three Consecutive Positions Starting from [(13)C(3)]-Propionic Acid
title_full_unstemmed Synthesis of [(13)C(3)]-B6 Vitamers Labelled at Three Consecutive Positions Starting from [(13)C(3)]-Propionic Acid
title_short Synthesis of [(13)C(3)]-B6 Vitamers Labelled at Three Consecutive Positions Starting from [(13)C(3)]-Propionic Acid
title_sort synthesis of [(13)c(3)]-b6 vitamers labelled at three consecutive positions starting from [(13)c(3)]-propionic acid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225105/
https://www.ncbi.nlm.nih.gov/pubmed/30142892
http://dx.doi.org/10.3390/molecules23092117
work_keys_str_mv AT bachmannthomas synthesisof13c3b6vitamerslabelledatthreeconsecutivepositionsstartingfrom13c3propionicacid
AT rychlikmichael synthesisof13c3b6vitamerslabelledatthreeconsecutivepositionsstartingfrom13c3propionicacid

Ejemplares similares