Synthesis of [13C3]-B6 vitamers labelled at three consecutive positions starting from [13C3]-propionic acid

Thomas Bachmann; Michael Rychlik

doi:10.3390/molecules23092117

Synthesis of [¹³C₃]-B6 vitamers labelled at three consecutive positions starting from [¹³C₃]-propionic acid

Thomas Bachmann
, Michael Rychlik

Chair of Analytical Food Chemistry

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

[¹³C₃]-labelled vitamers (PN, PL and PM) of the B6 group were prepared starting from [¹³C₃]-propionic acid. [¹³C₃]-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 [¹³C₃]-PN to [¹³C₃]-PL was undertaken using potassium permanganate and methylamine followed by acid hydrolysis of the imine derivative. [¹³C₃]-PM could be prepared from the oxime derivative of [¹³C₃]-PN by hydrogenation with palladium.

Original language	English
Article number	2117
Journal	Molecules
Volume	23
Issue number	9
DOIs	https://doi.org/10.3390/molecules23092117
State	Published - 23 Aug 2018

Keywords

Isotopologues
Labelled vitamers
Pyridoxal
Pyridoxamine
Pyridoxine
Synthesis
Vitamin B6

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10.3390/molecules23092117

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title = "Synthesis of [13C3]-B6 vitamers labelled at three consecutive positions starting from [13C3]-propionic acid",

abstract = "[13C3]-labelled vitamers (PN, PL and PM) of the B6 group were prepared starting from [13C3]-propionic acid. [13C3]-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 [13C3]-PN to [13C3]-PL was undertaken using potassium permanganate and methylamine followed by acid hydrolysis of the imine derivative. [13C3]-PM could be prepared from the oxime derivative of [13C3]-PN by hydrogenation with palladium.",

keywords = "Isotopologues, Labelled vitamers, Pyridoxal, Pyridoxamine, Pyridoxine, Synthesis, Vitamin B6",

author = "Thomas Bachmann and Michael Rychlik",

note = "Publisher Copyright: {\textcopyright} 2018 by the authors.",

year = "2018",

month = aug,

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doi = "10.3390/molecules23092117",

language = "English",

volume = "23",

journal = "Molecules",

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T1 - Synthesis of [13C3]-B6 vitamers labelled at three consecutive positions starting from [13C3]-propionic acid

AU - Bachmann, Thomas

AU - Rychlik, Michael

PY - 2018/8/23

Y1 - 2018/8/23

N2 - [13C3]-labelled vitamers (PN, PL and PM) of the B6 group were prepared starting from [13C3]-propionic acid. [13C3]-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 [13C3]-PN to [13C3]-PL was undertaken using potassium permanganate and methylamine followed by acid hydrolysis of the imine derivative. [13C3]-PM could be prepared from the oxime derivative of [13C3]-PN by hydrogenation with palladium.

AB - [13C3]-labelled vitamers (PN, PL and PM) of the B6 group were prepared starting from [13C3]-propionic acid. [13C3]-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 [13C3]-PN to [13C3]-PL was undertaken using potassium permanganate and methylamine followed by acid hydrolysis of the imine derivative. [13C3]-PM could be prepared from the oxime derivative of [13C3]-PN by hydrogenation with palladium.

KW - Isotopologues

KW - Labelled vitamers

KW - Pyridoxal

KW - Pyridoxamine

KW - Pyridoxine

KW - Synthesis

KW - Vitamin B6

UR - https://www.scopus.com/pages/publications/85052799510

U2 - 10.3390/molecules23092117

DO - 10.3390/molecules23092117

M3 - Article

C2 - 30142892

AN - SCOPUS:85052799510

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 9

M1 - 2117

ER -

Synthesis of [¹³C₃]-B6 vitamers labelled at three consecutive positions starting from [¹³C₃]-propionic acid

Abstract

Keywords

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