A Plausible Prebiotic Origin of Glyoxylate: Nonenzymatic Transamination Reactions of Glycine with Formaldehyde

作者:Mohammed Fiaz S; Chen Ke; Mojica Mike; Conley Mark; Napoline Jonathan W; Butch Christopher; Pollet Pamela; Krishnamurthy Ramanarayanan; Liotta Charles L
来源:Synlett, 2017, 28(1): 93-97.
DOI:10.1055/s-0036-1588657

摘要

Glyoxylate has been postulated to be an important prebiotic building block. However, a plausible prebiotic availability of glyoxylate has not as yet been demonstrated. Herein we report the formation of glyoxylate by means of a transamination reaction between glycine and formaldehyde in water at 50 degrees C and 70 degrees C at pH 8 and 6, respectively. The reaction was followed by means of C-13 NMR and high-resolution mass spectrometry employing both unlabeled and C-13-labeled reactants. Other products accompanying the transamination process include serine, sarcosine, N, N-dimethylglycine, and carbon dioxide/bicarbonate. The mechanisms for the formation of glyoxylate and accompanying products are discussed. 1 Introduction 2 Background 3 Results and Discussion 3.1 Reaction of C-13-Labeled Glycine with Formaldehyde at pH 8 3.2 Reaction of C-13-Labeled Glycine with Formaldehyde at pH 6 3.3 Serine-Promoted Decarboxylation of Glyoxylate 4 Conclusions

  • 出版日期2017-1