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

Abstract

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 °C and 70 °C at pH 8 and 6, respectively. The reaction was followed by means of ¹³C NMR and high-resolution mass spectrometry employing both unlabeled and ¹³C-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 ¹³C-Labeled Glycine with Formaldehyde at pH 8

3.2 Reaction of ¹³C-Labeled Glycine with Formaldehyde at pH 6

3.3 Serine-Promoted Decarboxylation of Glyoxylate

4 Conclusions

Key words

prebiotic - glycine - glyoxylate - serine - transamination - decarboxylation

• References and Notes

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