Template catalysis of acetyl transfer reactions

Chung, N.M.; Lohrmann, R.; Orgel, Leslie E.

doi:10.1016/0005-2787(71)90059-1

Cited by 12 publications

(3 citation statements)

References 7 publications

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“…Chung et al 23 did show sigtuficant enhancement of the transfer of acetyl from the adenylate anhydride to ester through complexation of acetyl adenylate with poly(U).…”

Section: Resultsmentioning

confidence: 97%

N‐Acetyl‐D and L‐esters of 5′‐AMP hydrolyze at different rates

Wickramasinghe

Lacey

1993

Chirality

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Studies of the properties of aminoacyl derivatives of 5'-AMP are aimed at understanding the origin of the process of protein synthesis. Aminoacyl (2',3') esters of 5'-AMP can serve as models of the 3'-terminus of aminoacyl tRNA. We report here on the relative rates of hydrolysis of Ac-D- and L-Phe AMP esters as a function of pH. At all pHs above 3, the rate constant of hydrolysis of the Ac-L-Phe ester is 1.7 to 2.1 times that of Ac-D-Phe ester. The D-isomer seems partially protected from hydrolysis by a stronger association with the adenine ring of the 5'-AMP.

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“…Chung et al 23 did show sigtuficant enhancement of the transfer of acetyl from the adenylate anhydride to ester through complexation of acetyl adenylate with poly(U).…”

Section: Resultsmentioning

confidence: 97%

N‐Acetyl‐D and L‐esters of 5′‐AMP hydrolyze at different rates

Wickramasinghe

Lacey

1993

Chirality

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“…For example, formation of complexes of adenylic acid derivatives has been used as the basis for experiments showing the formation of oligoadenylates on a poly U template (Sulston et al, 1968) and acetyl transfer from acetyl adenylate to adenosine while both are complexed with poly U (Chung et al, 1971).…”

Section: Discussionmentioning

confidence: 99%

A model for the coevolution of the genetic code and the process of protein synthesis: Review and assessment

Lacey

Weber

White

1975

Origins Life Evol Biosphere

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The contemporary genetic code and the process of protein biosynthesis most assuredly evolved from a simpler code and process. We believe that there was obligatory coevolution of the two and that the earlier code and process must have involved a more direct linkage between the amino acids and the information macromolecule. We propose that an early form of translating existed in which amino acids were attached directly to the 'messenger' RNA along the backbone as 2'OH aminoacyl esters. These esters then condensed with each other on the RNA backbone yielding a peptide covalently attached to the RNA, without the use of tRNA's and ribosomes. THis presentation is concerned with experimental data which indicate that such a simple translation system is possible and must have involved the following steps: (1) formation of the aminoacyl adenylate anhydride, (2) transfer of the amino acid from the adenylate to immidazole, (3) transfer of the amino acid from imidazole to 2'OH groups along the backbone of RNAs, (4) condensation of the amino acids to yield peptides. Steps (1)-(3) have been confirmed in chemical systems. Our preliminary evidence indicates step (4) is also possible. The aminoacylation of polyribonucleotides and the subsequent formation of peptides is a dynamic and experimentally accessible system for studying genetic coding specfities and our present studies are now concentrated on step (4), looking for such specifities.

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“…Template-directed polymerization mediates the translation of genetic information into functional macromolecules and ultimately enables the evolution of biopolymers. Over the past few decades, several researchers have explored the use of nucleic acid-templated polymerization reactions in the absence of enzymes to generate sequence-defined synthetic oligomers and polymers without the structural constraints imposed by the biosynthetic machinery. − The DNA- or RNA-templated polymerization of synthetic building blocks raises the possibility of performing test tube evolution on synthetic polymers toward desired functional properties through iterated cycles of translation (polymerization), selection, amplification, and mutation (as an example, see Figure ) 1 Example of a simplified scheme for the evolution of synthetic polymers using DNA-templated polymerization.…”

Section: Introductionmentioning

confidence: 99%

DNA-Templated Polymerization of Side-Chain-Functionalized Peptide Nucleic Acid Aldehydes

et al. 2008

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Abstract:The DNA-templated polymerization of synthetic building blocks provides a potential route to the laboratory evolution of sequence-defined polymers with structures and properties not necessarily limited to those of natural biopolymers. We previously reported the efficient and sequence-specific DNA-templated polymerization of peptide nucleic acid (PNA) aldehydes. Here, we report the enzyme-free, DNA-templated polymerization of side-chain-functionalized PNA tetramer and pentamer aldehydes. We observed that polymerization of tetramer and pentamer PNA building blocks with a single lysine-based side chain at various positions in the building block could proceed efficiently and sequence specifically. In addition, DNAtemplated polymerization also proceeded efficiently and in a sequence-specific manner with pentamer PNA aldehydes containing two or three lysine side chains in a single building block to generate more densely functionalized polymers. To further our understanding of side-chain compatibility and expand the capabilities of this system, we also examined the polymerization efficiencies of 20 pentamer building blocks each containing one of five different side-chain groups and four different side-chain regio-and stereochemistries. Polymerization reactions were efficient for all five different side-chain groups and for three of the four combinations of side-chain regio-and stereochemistries. Differences in the efficiency and initial rate of polymerization correlate with the apparent melting temperature of each building block, which is dependent on side-chain regio-and stereochemistry but relatively insensitive to side-chain structure among the substrates tested. Our findings represent a significant step toward the evolution of sequence-defined synthetic polymers and also demonstrate that enzyme-free nucleic acid-templated polymerization can occur efficiently using substrates with a wide range of side-chain structures, functionalization positions within each building block, and functionalization densities.

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Template catalysis of acetyl transfer reactions

Cited by 12 publications

References 7 publications

N‐Acetyl‐D and L‐esters of 5′‐AMP hydrolyze at different rates

N‐Acetyl‐D and L‐esters of 5′‐AMP hydrolyze at different rates

A model for the coevolution of the genetic code and the process of protein synthesis: Review and assessment

DNA-Templated Polymerization of Side-Chain-Functionalized Peptide Nucleic Acid Aldehydes

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