How Small Heterocycles Make a Reaction Network of Amino Acids and Nucleotides Efficient in Water
Abstract: Organisms use enzymes to ensure a flow of substrates through biosynthetic pathways. How the earliest form of life established biosynthetic networks and prevented hydrolysis of intermediates without enzymes is unclear. Organocatalysts may have played the role of enzymes. Quantitative analysis of reactions of adenosine 5’‐monophosphate and glycine that produce peptides, pyrophosphates, and RNA chains reveals that organocapture by heterocycles gives hydrolytically stabilized intermediates with balanced reactivity. We determined rate constants for 20 reactions in aqueous solutions containing a carbodiimide and measured product formation with cyanamide as a condensing agent. Organocapture favors reactions that are kinetically slow but productive, and networks, over single transformations. Heterocycles can increase the metabolic efficiency more than two‐fold, with up to 0.6 useful bonds per fuel molecule spent, boosting the efficiency of life‐like reaction systems in the absence of enzymes.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
How Small Heterocycles Make a Reaction Network of Amino Acids and Nucleotides Efficient in Water ; volume:131 ; number:37 ; year:2019 ; pages:13221-13226 ; extent:6
Angewandte Chemie ; 131, Heft 37 (2019), 13221-13226 (gesamt 6)
- Urheber
- DOI
-
10.1002/ange.201905427
- URN
-
urn:nbn:de:101:1-2022080106382136906273
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
2025-08-15T07:35:08+0200
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Tremmel, Peter
- Griesser, Helmut
- Steiner, Ulrich E.
- Richert, Clemens
Ähnliche Objekte (12)
How Small Heterocycles Make a Reaction Network of Amino Acids and Nucleotides Efficient in Water
Barcoded Nucleotides
The Enzyme‐Free Release of Nucleotides from Phosphoramidates Depends Strongly on the Amino Acid
Photoinduced Minisci Reaction with Diazines: An Approach Toward Original Fused Heterocycles.
SYNTHESES OF SIX- AND SEVEN-MEMBERED NITROGEN HETEROCYCLES FROM CYCLIC AMINO PHOSPHONIUM SALTS
Enantioselective Minisci-Reaction of N-Heterocycles and Amides through Hydrogen-Atom Transfer
Structural diversity using amino acid “Customizable Units”: conversion of hydroxyproline (Hyp) into nitrogen heterocycles
Pyridine Nucleotides in Biological Oxidations
Cyclic Nucleotides in Platelet Function
Stereoselective Synthesis of Phosphorothioate Nucleotides
Brook Rearrangement as Trigger for Dearomatization Reaction: Synthesis of Non‐Aromatic N ‐Heterocycles **
Chemische Berichte, Heterocycles
How Small Heterocycles Make a Reaction Network of Amino Acids and Nucleotides Efficient in Water
Barcoded Nucleotides
The Enzyme‐Free Release of Nucleotides from Phosphoramidates Depends Strongly on the Amino Acid
Photoinduced Minisci Reaction with Diazines: An Approach Toward Original Fused Heterocycles.
SYNTHESES OF SIX- AND SEVEN-MEMBERED NITROGEN HETEROCYCLES FROM CYCLIC AMINO PHOSPHONIUM SALTS
Enantioselective Minisci-Reaction of N-Heterocycles and Amides through Hydrogen-Atom Transfer
Structural diversity using amino acid “Customizable Units”: conversion of hydroxyproline (Hyp) into nitrogen heterocycles
Pyridine Nucleotides in Biological Oxidations
Cyclic Nucleotides in Platelet Function
Stereoselective Synthesis of Phosphorothioate Nucleotides
Brook Rearrangement as Trigger for Dearomatization Reaction: Synthesis of Non‐Aromatic N ‐Heterocycles **
Chemische Berichte, Heterocycles
How Small Heterocycles Make a Reaction Network of Amino Acids and Nucleotides Efficient in Water
Barcoded Nucleotides
The Enzyme‐Free Release of Nucleotides from Phosphoramidates Depends Strongly on the Amino Acid
Photoinduced Minisci Reaction with Diazines: An Approach Toward Original Fused Heterocycles.
SYNTHESES OF SIX- AND SEVEN-MEMBERED NITROGEN HETEROCYCLES FROM CYCLIC AMINO PHOSPHONIUM SALTS
Enantioselective Minisci-Reaction of N-Heterocycles and Amides through Hydrogen-Atom Transfer
Structural diversity using amino acid “Customizable Units”: conversion of hydroxyproline (Hyp) into nitrogen heterocycles
Pyridine Nucleotides in Biological Oxidations
Cyclic Nucleotides in Platelet Function
Stereoselective Synthesis of Phosphorothioate Nucleotides
Brook Rearrangement as Trigger for Dearomatization Reaction: Synthesis of Non‐Aromatic N ‐Heterocycles **