دورية أكاديمية

A Prebiotic Pathway to Nicotinamide Adenine Dinucleotide.

التفاصيل البيبلوغرافية
العنوان: A Prebiotic Pathway to Nicotinamide Adenine Dinucleotide.
المؤلفون: Bechtel M; Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377, Munich, Germany., Kurrle NJ; Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377, Munich, Germany., Trapp O; Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377, Munich, Germany.; Max-Planck-Institute for Astronomy, Königstuhl 17, 69117, Heidelberg, Germany.
المصدر: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Aug 27; Vol. 30 (48), pp. e202402055. Date of Electronic Publication: 2024 Jul 30.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 9513783 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3765 (Electronic) Linking ISSN: 09476539 NLM ISO Abbreviation: Chemistry Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Weinheim, Germany : Wiley-VCH
مواضيع طبية MeSH: NAD*/chemistry , NAD*/metabolism, Ammonia/chemistry ; Niacinamide/chemistry ; Niacinamide/analogs & derivatives ; Phosphorylation ; Prebiotics ; Adenosine Monophosphate/chemistry ; Catalysis ; Acetaldehyde/chemistry ; Oxidation-Reduction ; Water/chemistry ; Pyridinium Compounds/chemistry ; Flavin-Adenine Dinucleotide/chemistry ; Flavin-Adenine Dinucleotide/metabolism
مستخلص: Enzymes play a fundamental role in cellular metabolism. A wide range of enzymes require the presence of complementary coenzymes and cofactors to function properly. While coenzymes are believed to have been part of the last universal ancestor (LUCA) or have been present even earlier, the syntheses of crucial coenzymes like the redox-active coenzymes flavin adenine dinucleotide (FAD) or nicotinamide adenine dinucleotide (NAD + ) remain challenging. Here, we present a pathway to NAD + under prebiotic conditions starting with ammonia, cyanoacetaldehyde, prop-2-ynal and sugar-forming precursors, yielding in situ the nicotinamide riboside. Regioselective phosphorylation and water stable light activated adenosine monophosphate derivatives allow for topographically and irradiation-controlled formation of NAD + . Our findings indicate that NAD + , a coenzyme vital to life, can be formed non-enzymatically from simple organic feedstock molecules via photocatalytic activation under prebiotically plausible early Earth conditions in a continuous process under aqueous conditions.
(© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
References: J. B. Corliss, J.A. Baross, S.E. Hoffman, Oceanologica Acta 1981, 59–69.
W. Martin, J. Baross, D. Kelley, M. J. Russell, Micropor. Mesopor. Mater. 2008, 6, 805–814.
Y. Yamagata, H. Watanabe, M. Saitoh, T. Namba, Nature 1991, 352, 516–519.
L. M. Barge, R. E. Price, Nat. Geosci. 2022, 15, 976–981.
C. Huber, G. Wächtershäuser, Science 2006, 314, 630–632.
C. Sagan, J. Theor. Biol. 1973, 39, 195–200.
C. Sagan, B. N. Khare, Science 1971, 173, 417–420.
H. R. Hulett, J. Theor. Biol. 1969, 24, 56–72.
D. E. Hull, Nature 1960, 186, 693–694.
S. Ranjan, C. L. Kufner, G. G. Lozano, Z. R. Todd, A. Haseki, D. D. Sasselov, Astrobiology 2021, 22, 242–262.
C. Bonfio, L. Valer, S. Scintilla, S. Shah, D. J. Evans, L. Jin, J. W. Szostak, D. D. Sasselov, J. D. Sutherland, S. S. Mansy, Nat. Chem. 2017, 9, 1229.
B. L. Hess, S. Piazolo, J. Harvey, Nat. Commun. 2021, 12, 1535.
S. L. Miller, Science 1953, 117, 528–529.
S. L. Miller, H. C. Urey, Science 1959, 130, 245–251.
W. Gilbert, Nature 1986, 319, 618.
H. B. White, J. Mol. Evol. 1976, 7, 101–104.
A. Kirschning, Nat. Prod. Rep. 2022, 39, 2175–2199.
J. Oró, Biochem. Biophys. Res. Com. 1960, 2, 407–412.
S. Becker, I. Thoma, A. Deutsch, T. Gehrke, P. Mayer, H. Zipse, T. Carell, Science 2016, 352, 833–836.
H.-J. Kim, S. A. Benner, PNAS 2017, 114, 11315.
J. E. V. Trump, S. L. Miller, Science 1972, 178, 859–860.
A. D. Keefe, G. L. Newton, S. L. Miller, Nature 1995, 373, 683–685.
A. Kirschning, Angew. Chem. Int. Ed. 2021, 60, 6242–6269.
A. Kirschning, Nat. Prod. Rep. 2021, 38, 993–1010.
P. Macheroux, B. Kappes, S. E. Ealick, FEBS Lett. 2011, 278, 2625–2634.
N. Pollak, C. Dölle, M. Ziegler, Biochem. J. 2007, 402, 205–218.
T. Seidenberger, J. Siepmann, H. Bley, K. Maeder, F. Siepmann, Int. J. Pharm. 2011, 412, 68–76.
M. J. Dowler, W. D. Fuller, L. E. Orgel, R. A. Sanchez, Science 1970, 169, 1320–1321.
H. Kim, S. A. Benner, Chem. Eur. J. 2018, 24, 581–584.
J. S. Teichert, F. M. Kruse, O. Trapp, Angew. Chem. Int. Ed. 2019, 58, 9944–9947.
C. Ponnamperuma, R. Mack, Science 1965, 148, 1221–1223.
C. Gibard, S. Bhowmik, M. Karki, E.-K. Kim, R. Krishnamurthy, Nat. Chem. 2018, 10, 212–217.
O. R. Maguire, I. B. A. Smokers, W. T. S. Huck, Nat. Commun. 2021, 12, 5517.
A. M. Schoffstall, Orig. Life 1976, 7, 399–412.
M. Bechtel, E. Hümmer, O. Trapp, ChemSystemsChem 2022, 4, e202200020.
M. Bechtel, M. Ebeling, L. Huber, O. Trapp, Acc. Chem. Res. 2023, 56, 2801–2813.
A. C. Closs, M. Bechtel, O. Trapp, Angew. Chem. Int. Ed. 2022, 61, e202112563.
C. Closs, E. Fuks, M. Bechtel, O. Trapp, Chem. Eur. J. 2020, 26, 10702–10706.
A. Mariani, D. A. Russell, T. Javelle, J. D. Sutherland, J. Am. Chem. Soc. 2018, 140, 8657–8661.
L. Li, N. Prywes, C. P. Tam, D. K. O'Flaherty, V. S. Lelyveld, E. C. Izgu, A. Pal, J. W. Szostak, J. Am. Chem. Soc. 2017, 139, 1810–1813.
W. Zhang, A. Pal, A. Ricardo, J. W. Szostak, J. Am. Chem. Soc. 2019, 141, 12159–12166.
S. Neubauer, A. Rugova, D. B. Chu, H. Drexler, A. Ganner, M. Sauer, D. Mattanovich, S. Hann, G. Koellensperger, Anal. Bioanal. Chem. 2012, 404, 799–808.
معلومات مُعتمدة: Molecular Life Volkswagen Foundation; 364653263 Deutsche Forschungsgemeinschaft; 390783311 Deutsche Forschungsgemeinschaft
فهرسة مساهمة: Keywords: Coenzyme; Nucleotide; Phosphorylation; Prebiotic chemistry; Ribose
المشرفين على المادة: 0U46U6E8UK (NAD)
7664-41-7 (Ammonia)
25X51I8RD4 (Niacinamide)
0 (Prebiotics)
0I8H2M0L7N (nicotinamide-beta-riboside)
415SHH325A (Adenosine Monophosphate)
GO1N1ZPR3B (Acetaldehyde)
059QF0KO0R (Water)
0 (Pyridinium Compounds)
146-14-5 (Flavin-Adenine Dinucleotide)
تواريخ الأحداث: Date Created: 20240617 Date Completed: 20240828 Latest Revision: 20240828
رمز التحديث: 20240828
DOI: 10.1002/chem.202402055
PMID: 38884181
قاعدة البيانات: MEDLINE