Carbonyl Migration in Uronates Affords a Potential Prebiotic Pathway for Pentose Production.
Journal
JACS Au
ISSN: 2691-3704
Titre abrégé: JACS Au
Pays: United States
ID NLM: 101775714
Informations de publication
Date de publication:
25 Sep 2023
25 Sep 2023
Historique:
received:
08
06
2023
revised:
15
08
2023
accepted:
15
08
2023
medline:
29
9
2023
pubmed:
29
9
2023
entrez:
29
9
2023
Statut:
epublish
Résumé
Carbohydrate biosynthesis is fundamental to modern terrestrial biochemistry, but how this collection of metabolic pathways originated remains an open question. Prebiotic sugar synthesis has focused primarily on the formose reaction and Kiliani-Fischer homologation; however, how they can transition to extant biochemical pathways has not been studied. Herein, a nonenzymatic pathway for pentose production with similar chemical transformations as those of the pentose phosphate pathway is demonstrated. Starting from a C6 aldonate, namely, gluconate, nonselective chemical oxidation yields a mixture of 2-oxo-, 4-oxo-, 5-oxo-, and 6-oxo-uronate regioisomers. Regardless at which carbinol the oxidation takes place, carbonyl migration enables β-decarboxylation to yield pentoses. In comparison, the pentose phosphate pathway selectively oxidizes 6-phosphogluconate to afford the 3-oxo-uronate derivative, which undergoes facile subsequent β-decarboxylation and carbonyl migration to afford ribose 5-phosphate. The similarities between these two pathways and the potential implications for prebiotic chemistry and protometabolism are discussed.
Identifiants
pubmed: 37772180
doi: 10.1021/jacsau.3c00299
pmc: PMC10523364
doi:
Types de publication
Journal Article
Langues
eng
Pagination
2522-2535Informations de copyright
© 2023 The Authors. Published by American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
Références
J Pharm Sci. 2016 Feb;105(2):705-713
pubmed: 26422524
Mol Syst Biol. 2014 Apr 25;10:725
pubmed: 24771084
Nat Chem. 2020 Nov;12(11):1016-1022
pubmed: 33046840
J Am Chem Soc. 2011 Jun 22;133(24):9457-68
pubmed: 21553892
Chem Rev. 2014 Jan 8;114(1):285-366
pubmed: 24171674
Proc Natl Acad Sci U S A. 2020 Jan 14;117(2):883-888
pubmed: 31888981
J Am Chem Soc. 2012 Feb 22;134(7):3577-89
pubmed: 22280414
Org Biomol Chem. 2020 Nov 7;18(41):8459-8466
pubmed: 33057544
Carbohydr Res. 2007 Feb 26;342(3-4):407-18
pubmed: 17204258
Carbohydr Res. 1991 Jan 15;209:13-31
pubmed: 1828004
Chem Biol Drug Des. 2007 Jul;70(1):30-9
pubmed: 17630992
Biochem J. 1955 Jun;60(2):271-4
pubmed: 14389236
Life (Basel). 2020 Jul 28;10(8):
pubmed: 32731352
Proc Natl Acad Sci U S A. 1999 Apr 13;96(8):4396-401
pubmed: 10200273
Front Bioeng Biotechnol. 2022 May 16;10:864787
pubmed: 35651548
Nat Chem. 2022 Oct;14(10):1142-1150
pubmed: 35902742
Biochemistry. 1998 Sep 8;37(36):12596-602
pubmed: 9730832
Sci Rep. 2021 Sep 29;11(1):19356
pubmed: 34588537
Proc Natl Acad Sci U S A. 2023 Mar 28;120(13):e2221984120
pubmed: 36940327
Chemistry. 2018 Nov 13;24(63):16708-16715
pubmed: 29870593
Nat Chem. 2023 Oct;15(10):1470-1477
pubmed: 37443293
Biochem J. 1986 Mar 15;234(3):671-7
pubmed: 3718491
Nat Commun. 2021 Nov 16;12(1):6611
pubmed: 34785682
Life (Basel). 2022 Jan 28;12(2):
pubmed: 35207486
Biophys Chem. 1985 Aug;22(3):197-204
pubmed: 3931718
J Am Chem Soc. 2014 Mar 12;136(10):3720-3
pubmed: 24575857
Chem Sci. 2022 Mar 23;13(17):4838-4853
pubmed: 35655880
Life (Basel). 2019 Nov 14;9(4):
pubmed: 31739415
J Org Chem. 2006 Dec 8;71(25):9503-5
pubmed: 17137382
Annu Rev Biochem. 1955;24:207-74
pubmed: 13249356
Cryst Growth Des. 2022 Apr 6;22(4):2307-2317
pubmed: 35401055
J Bacteriol. 1957 Apr;73(4):452-60
pubmed: 13428674
Orig Life Evol Biosph. 1988;18(1-2):71-85
pubmed: 2453009
Carbohydr Res. 2004 Jun 22;339(9):1609-18
pubmed: 15183735
Proc Natl Acad Sci U S A. 2020 Jun 16;117(24):13267-13274
pubmed: 32487725
Nat Chem. 2022 Feb;14(2):170-178
pubmed: 35115655
Nat Geosci. 2020 May;13(5):344-348
pubmed: 32395178
Orig Life Evol Biosph. 1995 Jun;25(1-3):83-98
pubmed: 11536683
J Mol Evol. 1999 Oct;49(4):424-31
pubmed: 10486000
Chem Rev. 2020 Aug 12;120(15):7708-7744
pubmed: 32687326
Astrobiology. 2020 Apr;20(4):429-452
pubmed: 31841362
Orig Life Evol Biosph. 2001 Feb-Apr;31(1-2):87-102
pubmed: 11296526
Proc Natl Acad Sci U S A. 2019 Dec 3;116(49):24440-24445
pubmed: 31740594
Sci Adv. 2016 Jan 15;2(1):e1501235
pubmed: 26824074
Chem Commun (Camb). 2020 Nov 14;56(88):13563-13566
pubmed: 33151212
Proc Natl Acad Sci U S A. 1995 Aug 29;92(18):8158-60
pubmed: 7667262
Science. 2004 Jan 9;303(5655):196
pubmed: 14716004
Nat Chem. 2012 Nov;4(11):895-9
pubmed: 23089863
Carbohydr Res. 2010 Feb 11;345(3):377-84
pubmed: 20034621
Nature. 2001 Dec 20-27;414(6866):879-83
pubmed: 11780054
Chemistry. 2023 Feb 7;29(8):e202202816
pubmed: 36367459
Ann N Y Acad Sci. 1961 Apr 21;92:105-14
pubmed: 13684759