Synthesis of 4-Deoxy-4-Fluoro-d-Sedoheptulose: A Promising New Sugar to Apply the Principle of Metabolic Trapping.
d-sedoheptulose
fluorinated carbohydrates
metabolic trapping
pentose phosphate pathway
rare sugars
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
08 Nov 2023
08 Nov 2023
Historique:
received:
17
07
2023
medline:
10
11
2023
pubmed:
8
8
2023
entrez:
8
8
2023
Statut:
ppublish
Résumé
Fluorinated carbohydrates are important tools for understanding the deregulation of metabolic fluxes and pathways. Fluorinating specific positions within the sugar scaffold can lead to enhanced metabolic stability and subsequent metabolic trapping in cells. This principle has, however, never been applied to study the metabolism of the rare sugars of the pentose phosphate pathway (PPP). In this study, two fluorinated derivatives of d-sedoheptulose were designed and synthesized: 4-deoxy-4-fluoro-d-sedoheptulose (4DFS) and 3-deoxy-3-fluoro-d-sedoheptulose (3DFS). Both sugars are taken up by human fibroblasts but only 4DFS is phosphorylated. Fluorination of d-sedoheptulose at C-4 effectively halts the enzymatic degradation by transaldolase and transketolase. 4DFS thus has a high potential as a new PPP imaging probe based on the principle of metabolic trapping. Therefore, the synthesis of potential radiolabeling precursors for 4DFS for future radiofluorinations with fluorine-18 is presented.
Identifiants
pubmed: 37552007
doi: 10.1002/chem.202302277
doi:
Substances chimiques
sedoheptulose
3019-74-7
Sugars
0
Heptoses
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302277Subventions
Organisme : Austrian Science Fund
ID : P32421-N28
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
Genes Dev. 2016 Feb 15;30(4):355-85
pubmed: 26883357
Clin Cancer Res. 2010 Feb 1;16(3):857-66
pubmed: 20103683
J Med Chem. 2015 Jul 23;58(14):5538-47
pubmed: 26102222
Hum Mutat. 2008 Apr;29(4):532-6
pubmed: 18186520
Org Lett. 2013 Oct 4;15(19):4948-51
pubmed: 24032575
J Nucl Med. 1978 Oct;19(10):1154-61
pubmed: 214528
Angew Chem Int Ed Engl. 2014 Jul 7;53(28):7328-34
pubmed: 24895187
Molecules. 2015 Mar 03;20(3):4020-41
pubmed: 25741897
Chem Commun (Camb). 2016 May 4;52(36):6083-6
pubmed: 27043419
Trends Biochem Sci. 2014 Aug;39(8):347-54
pubmed: 25037503
Angew Chem Int Ed Engl. 2005 Mar 4;44(11):1665-8
pubmed: 15685675
Cancer Res. 2007 Feb 15;67(4):1472-86
pubmed: 17308085
Cell Metab. 2012 Jun 6;15(6):813-26
pubmed: 22682222
Org Biomol Chem. 2011 Apr 7;9(7):2209-18
pubmed: 21301710
Chemistry. 2023 Nov 8;29(62):e202302277
pubmed: 37552007
Proc Natl Acad Sci U S A. 2014 Jul 15;111(28):E2866-74
pubmed: 24982199
Metab Eng. 2006 Nov;8(6):639-52
pubmed: 16904360
Protein Cell. 2014;5(8):592-602
pubmed: 25015087
J Org Chem. 2022 Jan 21;87(2):1272-1284
pubmed: 34964642
Nature. 2009 Jun 4;459(7247):717-21
pubmed: 19412164
FEBS Lett. 2008 Oct 15;582(23-24):3330-4
pubmed: 18775706
Anticancer Drugs. 2007 Apr;18(4):427-33
pubmed: 17351395
Genome Res. 2000 Feb;10(2):165-73
pubmed: 10673275
Int J Cancer. 2008 Jun 1;122(11):2422-8
pubmed: 18302154
Genes Chromosomes Cancer. 2004 Jun;40(2):97-108
pubmed: 15101043
J Org Chem. 2016 Nov 18;81(22):10769-10790
pubmed: 27736093
Cancer Lett. 2007 Aug 8;253(1):108-14
pubmed: 17321041
Org Lett. 2011 Jul 15;13(14):3628-31
pubmed: 21671612
Imaging Sci Dent. 2014 Dec;44(4):325-32
pubmed: 25473642
Chem Soc Rev. 2020 Jun 22;49(12):3863-3888
pubmed: 32520059
Biochem Soc Trans. 2013 Apr;41(2):674-80
pubmed: 23514175
Am J Pathol. 2005 Dec;167(6):1763-75
pubmed: 16314486