Stereoselective formation of bis(α-aminoacyl) esters of 5′-AMP suggests a primitive peptide synthesizing system with a preference for l-amino acids

Lacey, James C.; Thomas, Ralph D.; Staves, Mark P.; Watkins, Charles L.

doi:10.1016/0167-4838(91)90482-f

Cited by 17 publications

(8 citation statements)

References 6 publications

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“…An identical reaction was carried out in heavy water and the analysis of the reaction medium at 3 h allowed the observation of signals at 5.28 and 5.05 for the 2’‐and 3’‐protons of the phosphodiester 2’,3’‐cAMP (c=cyclic adenosine monophosphate), which could be confirmed by HPLC‐MS with the observation of a signal at 1.24 min (ESI − , m/z =328.0455 Da). Additional signals were observed at 5.51 and 5.61 ppm, which were considered as characteristic of the 2’‐protons of the ribose moiety of aminoacylated species and therefore, correspond to the presence of esters such as 10 and 12 (Scheme ). This assignment could be confirmed by acidifying the solution to about pH 2, a procedure known to destroy any PEMA that could be present in the medium .…”

Section: Resultsmentioning

confidence: 99%

Mixed Anhydride Intermediates in the Reaction of 5(4H)‐Oxazolones with Phosphate Esters and Nucleotides

Liu

Rigger

Rossi

et al. 2016

Chemistry A European J

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Abstract5(4H)‐Oxazolones can be formed through the activation of acylated α‐amino acids or of peptide C termini. They constitute potentially activated intermediates in the abiotic chemistry of peptides that preceded the origin of life or early stages of biology and are capable of yielding mixed carboxylic‐phosphoric anhydrides upon reaction with phosphate esters and nucleotides. Here, we present the results of a study aimed at investigating the chemistry that can be built through this interaction. As a matter of fact, the formation of mixed anhydrides with mononucleotides and nucleic acid models is shown to take place at positions involving a mono‐substituted phosphate group at the 3’‐ or 5’‐terminus but not at the internal phosphodiester linkages. In addition to the formation of mixed anhydrides, the subsequent intramolecular acyl or phosphoryl transfers taking place at the 3’‐terminus are considered to be particularly relevant to the common prebiotic chemistry of α‐amino acids and nucleotides.

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Section: Resultsmentioning

confidence: 99%

Mixed Anhydride Intermediates in the Reaction of 5(4H)‐Oxazolones with Phosphate Esters and Nucleotides

Liu

Rigger

Rossi

et al. 2016

Chemistry A European J

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“…So, although the above-mentioned study ) was carried out using freshly prepared L-amino acid imidazolides, most assuredly some D-isomer was present but in unknown amounts. Furthermore, as will be discussed more thoroughly later, bis 2', 3' esters of Y-AMP are very readily formed (Lacey et al, 1991a). So, in the earlier study ) the hydroxamate assay would be the total for mono-and diesters, and we don't know how much diester was present.…”

Section: R E a C T I O N F O R M I N G Estersmentioning

confidence: 97%

“…The rate constants derived from these data are 0.08 min I for disappearance of the Ac-L-Phe AMP monoester and 0.03 for disappearance of Ac-D-Phe AMP monoester. The products of the reaction are the bis 2', 3' AMP esters (Lacey et al, 1991a).…”

Section: H I R a L D I F F E R E N C E Smentioning

confidence: 99%

Experimental studies on the origin of the genetic code and the process of protein synthesis: A review update

Lacey

Wickramasinghe

Cook

1992

Origins Life Evol Biosphere

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This article is an update of our earlier review (Lacey and Mullins, 1983) in this journal on the origin of the genetic code and the process of protein synthesis. It is our intent to discuss only experimental evidence published since then although there is the necessity to mention the old enough to place the new in context. We do not include theoretical nor hypothetical treatments of the code or protein synthesis. Relevant data regarding the evolution of tRNAs and the recognition of tRNAs by aminoacyl-tRNA-synthetases are discussed. Our present belief is that the code arose based on a core of early assignments which were made on a physico-chemical and anticodonic basis and this was expanded with new assignments later. These late assignments do not necessarily show an amino acid-anticodon relatedness. In spite of the fact that most data suggest a code origin based on amino acid-anticodon relationships, some new data suggesting preferential binding of Arg to its codons are discussed. While information regarding coding is not increasing very rapidly, information regarding the basic chemistry of the process of protein synthesis has increased significantly, principally relating to aminoacylation of mono- and polyribonucleotides. Included in those studies are several which show stereoselective reactions of L-amino acids with nucleotides having D-sugars. Hydrophobic interactions definitely play a role in the preferences which have been observed.

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“…-adcnosine was synthcsized and purified according to [9]. A'-acetyl-L-["C]phenylalanine was prepnred as in [lo], 5'.O-dimrthoxytrityladenosine was prepared as in [I I].…”

Section: Homogeneous Phersase From T/1rrm4smentioning

confidence: 99%

Phenylalanyl‐tRNA synthetase from Thermus thermophilus can attach two molecules of phenylalanine to tRNA^Phe

et al. 1992

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Phenylalanyl‐tRNA synthetase from the extreme thermophilic bacterium Thermus thermophilus can incorporate more than one molecule of phenylalanine into the tRNAPhe. It is shown that the ‘hyperaminoncylated’ tRNAPPhe is the bis‐2′,3′‐O‐phenylalanyl‐tRNAPhe, and its formation is typical for the thermophilic enzyme but does not occur for E. coli phenylalanyl‐tRNA synthetase under the same conditions.

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Stereoselective formation of bis(α-aminoacyl) esters of 5′-AMP suggests a primitive peptide synthesizing system with a preference for l-amino acids

Cited by 17 publications

References 6 publications

Mixed Anhydride Intermediates in the Reaction of 5(4H)‐Oxazolones with Phosphate Esters and Nucleotides

Mixed Anhydride Intermediates in the Reaction of 5(4H)‐Oxazolones with Phosphate Esters and Nucleotides

Experimental studies on the origin of the genetic code and the process of protein synthesis: A review update

Phenylalanyl‐tRNA synthetase from Thermus thermophilus can attach two molecules of phenylalanine to tRNA^Phe

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Stereoselective formation of bis(α-aminoacyl) esters of 5′-AMP suggests a primitive peptide synthesizing system with a preference for l-amino acids

Cited by 17 publications

References 6 publications

Mixed Anhydride Intermediates in the Reaction of 5(4H)‐Oxazolones with Phosphate Esters and Nucleotides

Mixed Anhydride Intermediates in the Reaction of 5(4H)‐Oxazolones with Phosphate Esters and Nucleotides

Experimental studies on the origin of the genetic code and the process of protein synthesis: A review update

Phenylalanyl‐tRNA synthetase from Thermus thermophilus can attach two molecules of phenylalanine to tRNAPhe

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Phenylalanyl‐tRNA synthetase from Thermus thermophilus can attach two molecules of phenylalanine to tRNA^Phe